Chicago Skyline

We visited Chicago in April 2008 and before we left, we asked for suggestions of all the things we really shouldn’t miss. Below is an excellent list of ideas so kindly given to us by Chicagoans, former Chicagoans, and people who really just like Chicago a whole bunch. I have the feeling that pretty much every suggestion on this list is absolutely excellent, but of course we couldn’t try it all; of what we did try, we loved Giordano’s for pizza, the miniature room at the Art Institute, having a drink in the Signature Room of the Hancock Building, catching a show at Second City, the Bongo Room for brunch, and Café Iberico for tapas. We stayed at the Four Points Sheraton just off Michigan Avenue; the location was fabulous and the staff extremely friendly.

98 Reader Suggestions

Jules says:

I just typed up a list for my friends who came to Chicago for a weekend getaway. It's way too long to leave in the comments, so I'll email it to you! Have a great time in my city!
Jules
House of Jules

Rachael W says:

I've only ever been to O'Hare and Midway, but I had to comment because I know where Sean's coming from. I am exactly the same way about baseball, only my team is the Cleveland Indians. And yes, I have traveled to other cities so that I can see them more than once or twice a season.

Heather B. says:

1) I have the Yankees schedule/site bookmarked as well. Ok fine. From March to October it is actually my homepage.

2) Good lord. That trip you went on to Chicago over the summer was exhausting by the end. Especially that last night when it seemed to be a good idea to stay up late even though we both had ass crack of dawn flights. That was fun. When I say that I want to go to Chicago I keep getting reminded that I was just there. Uh, no. I went to the Navy Pier and the W (to pilfer Bliss products of course) and that was all.

Oh and the one time I went to Chicago before that was for my 16th birthday. We saw Oprah and got deep dish pizza. So if you can do the former, awesome. But definitely partake in the latter.

Eva says:

Never mind the wind, just watch out for the plummeting helicopters.

Eva says:

Ooh, the Plummeting Helicopters would be a great name for a noisy, guitar-y, rousing-chorus-y band.

sgazzetti says:

I have no knowledge whatsoever of Chicago, but I wanted to tell you that Future girlfriends of Sean, beware! cracked me up.

Teej says:

OK. Here's what you do.

You can go to Gino's for pizza if you want, but the best pizza in Chicago, in my opinion, is Giordano's. Skip Gino's entirely unless you feel compelled to do it. There are several Giordano's locations and it's truly DELISH, even the thin crust (pepperoni and onion is my favorite). (If you feel compelled to do Gino's because it's the touristy thing to do, I would not go to that giant, new, obnoxious Gino's downtown on Wells. It will be crawling with tourists. If you just want the pizza, maybe try the tiny Gino's on Lincoln.)

Please go to Cafe Baba-Reeba! in Lakeview (which is a neighbohood) on Halsted street. Super delicious tapas, and they should have the covered courtyard open by now. That's our favorite casual restaurant in the city. Try the peach sangria if you're a fan of sweetness.

A super touristy thing that I sort of enjoyed taking people to was the giant Ferris wheel on Navy Pier. Navy Pier is also crawling with tourists, but what can I say? I like the giant Ferris wheel.

Chicago has great museums -- and you already mentioned the Art Institute. But if you go to the Art Institute, PLEASE tell me that you'll go downstairs and check out the miniatures. This woman spent her life making miniature models -- dioramas, I guess? -- of rooms from periods throughout history. A 1740s farmhouse kitchen from Maryland! And 13th-century bedroom from Scotland! They're amazing and the detail is completely mind-blowing.

You might consider walking along Armitage in Lakeview for an afternoon -- good shopping, nice places to stop for a drink or food.

There's always the Frank Lloyd Wright house in Oak Park, which is not far outside the city -- just due west on I-290 for a moment. If you like that sort of thing, it's wonderful.

I also like to take people to the Signature Room lounge of the Hancock Building. Beware: Drinks are ridiculously overpriced. But it's right on the Lake and has an amazing view in clear weather. People never understand how big Lake Michigan is until they get up there. It could be an ocean from that vantage point -- seems to go on forever.

Another yummy dinner spot -- a little fancier than Baba-Reeba! -- is Japonais. It's on the river and the sushi is delish.

You could shop along Michigan Avenue and Oak Street. There's a little area bounded by Chicago, State and Rush that people call the Viagra Triangle because it's packed with old men scamming on not-so-young women. And morons who drive their really expensive cars around the block 50 times for everybody to see. BUT -- Gibson's, which is one of the restaurants there -- has the most delicious mini-filet sandwiches ever. Eat them for lunch, but only if you can sit outside. The inside is kind of a drag.

That's all I can think of for now. If I think of anything else, I'll holler.

Teej says:

Holy crap, my comment is full of punctuation mistakes. Sorry -- 7:30 a.m. is early in my world. Now if you'll excuse me, my pillow is calling. Again.

Superfantastic says:

I second the recommendation for Giordano's. And if you do decide to roadtrip into Wisconsin rather than Michigan, email me and I can give you all kinds of information, particularly if you're interested in Madison. (Definitely the best and most visit-worthy place in Wisconsin, unless you're looking for some sort of authentic dairy farm experience, in which case I cannot help you. Although I can certainly advise you on your cheese purchases.)

Vicki says:

Hi Holly,
I have no recommendations about Chicago whatsoever for you, but I did want to say that I'm flying from France to Chicago for the first time ever next Thursday to visit a friend, and I can't wait!

I'll be keeping an eye on your comments box to check out all the tips your readers send in, and then I'll most probably be stealing them for my own trip.

Ooh no actually I do have one recommendation, my best friend works at a fabulous French restaurant called Bistro Margot in the Old Town, you should eat there and ask for Leah! And then you should say hi to the English girl who'll be propping up the bar in there, 'cos that'll be me waiting for Leah's shift to finish so she can show me the 'real' Chicago!
Also if you do see me feel free to tell me where I can buy your awesome lipslicks from so I can take a crate of them back to France with me!
Cheers!

Jessi says:

Besides the pizza (totally agree with Teej, I was none too impressed with Gino's), there are also two other essential Chicago foods - a Chicago style hot dog and Chicago mix popcorn!

The skinny on the hotdog - there are a few places to get them, but I prefer a place called "Super Dawg" - it is kind of in the suburbs of Chicago (can't remember where, but if you google it, it's the one on Milwaukee Ave) - the dogs are all beef, mustard, ketchup, onions, jalapeno peppers, pickles, and - the best part - day glo relish! The dogs are super good, and Super Dawg is an old style drive in restaurant.

And the popcorn...a mix of sweet and salty, and something wonderful! You can get it at Garrett's Popcorn. There are a few locations around the city; I believe there is one near the Art Institute, and I know there is one right across Michigan Avenue from the Apple Store (which is totally huge BTW).

Hope that helps - enjoy your trip!

leandra says:

Yes, it will be windy! The weather can be very unpredictable in April, so I'm sending warm weather vibes your way.

I second Teej on the miniature rooms at the Art Institute and the humongous glass paperweight collection is amazing too!

I also highly recommend the Field Museum (near Shedd Aquarium), it could take a week to get through the whole place but Sue and the Hall of Gems is worth the price of admission, imho. Enjoy!

Katie says:

Chicago rocks. One of my favorite trips there (with my best friend, which is totally what made it radical) involved a very late night trip to a place called The Weiner Circle, which is definitely an experience. If you're going super late, best to be d-runk. I hear if you go earlier, the atmosphere is more fun than, say, mean spirited. Their hot dogs are very good.

Jacqui says:

The area off the Blue Line Damen El stop in Wicker Park/Bucktown has really changed in the past few years. It is becoming less hipster and more family oriented, so new boutiques have opened on Damen. I love City Sole on Damen for shoes.They have some unique options, and there is always a giant pile of sale shoes to search through. Go to Handlebar in Wicker Park for some delicious vegetarian food and desert (flourless chocolate cake). This is the kind of bar which doesn't have a television (not fancy, just not sport-sy) has a good selection of beers and a nice patio.

Toast(on Damen in Bucktown or Webster in Lincoln Park) for brunch is a nice option, but the wait is LONG, so go early morning or close to closing if it is Saturday or Sunday.

Maren says:

On your way to visit Madison and Superfantastic, you can come see my pond - it has DUCKS! and MUSKRATS! It just doesn't get any better than that really. And if you are, in fact, interested in the dairy farm experience, I CAN help you with that - oh, and the cheese, you definitely need to get some cheese, straight from the factory, it really is the only way.

Jacqui says:

IMHO, avoid Wiener Circle at all costs. But I am not a Lincoln Park bar crowd kind of girl. Too frat party for me.
I forgot to mention that the Field Museum has an exhibit entitled, "Mythic Creatures" right now. I think there will be unicorns. And the Museum of Contemporary Art is always great. Karen Kilimnik has an exhibit there right now.

Amanda says:

I second heading up the Blue Line to Wicker Park/Bucktown. Great boutique shopping down Damen Ave with restaurants and bars to pop into--including Toast, which was mentioned above. While Toast is fab, the wait really is LONG, so I'd suggest heading to another nearby place, Hot Chocolate.

And while everyone's talking pizza and hotdogs, I have to recommend a burger place--Kuma's near California and Belmont. Kind of out of the way from downtown but it's AMAZING.

Touristy-wise, you have to go see the Bean (Cloud Gate)at Millennium Park. Take some fun/wacky pictures and then walk over to Buckingham Fountain for another signature Chicago postcard shot.

I could probably come up with about 100 other things to do here. I love my hometown!

Charise says:

HAH! I have girls' nights 2-3 Wednesdays a month, and on the weeks I don't, my fiance gets all sad and says "I don't get my me time?", which means he doesn't get to spend 4 hours playing computer games with the sound at a mindblowing level. Because I will be in the other room and CAN NOT HANDLE all that noise.

I grew up in the suburbs of Chicago so I was going to have a few suggestions for you but many have already been given: Giordano's, Garret's, etc. You could go ahead and get a Chicago-style hot dog at the ballpark to get two things out of the way at once. If you like Mexican, try Frontera or Topolobampo, Rick Bayless' restaurants. I will try to think of others, but I haven't been back much in the last few years.

My favorite museum is the Museum of Science and Industry. You should see the bean in Millenium Park, some fun pictures can be had with that. For a family reunion one year, we took everyone on an architechture cruise, where you go down the Chicago River and get told the history of all the cool old buildings. A bit touristy, but interesting if you are into that kind of thing.

Lara says:

Oh I fully support Giordano's over Gino's. The deep dish pizza, mmmmmm....maybe that will be lunch today. Ba-Ba-Reeba is alright, but my all-time favorite for tapas is Twist in Wrigley. Tiny place, not well known but oh so delicious.

If the weather's nice take the Brown line to Southport and check out all the bars, restaurants, boutiques, etc. Ethel's chocolates will give you free samples if you ask! Sit out on the street at one of the many cafes/bars/restaurants & watch as the whole neighborhood takes their dog for a walk. Check out the consignment shop for some good finds, too. There's even something in it for Sean, because when you're done you can walk a few blocks down Addison & check out Wrigley Field. Fun for the whole family!

I love my city.

Lara says:

Totally did not read Amanda's comment about her hometown when I wrote mine. Man, we are some Chicago-lovin' nerds (aka AWESOME people).

Diane says:

Garrett's is a must do - it is the best popcorn EVER! And I agree with Teej on just about everything she said to do in her comment. I used to date a guy who lived in Chicago and I loved every weekend that I went there. It is such a fun city and very easy to get around.

Love it all and whatever you do you can't go wrong! Sean should make his way to Toronto for a game as we play the Yankees usually twice a season!

PS - the line about Sean's future girlfriend made me snort at my desk!

g says:

I went to college in Chicago over ten years ago so these recommendations might be outdated. We used to love tapas at Cafe Iberico and nicer dinners at Frontera Grill. On the museum front, I second the recommendations for the Field Museum and the Museum of Science and Industry. Have a great trip!

Christina says:

I have to second Teej's comment about Baba-Reeba... seriously yummy food.

Also, if you happen to hit up Lincoln Park (excellent shopping!) stop by McGee's for a beer and some Irish nachos. I know, I know, it's not deep dish pizza, or a 4-star restaurant, but they're nachos - MADE WITH WAFFLE FRIES INSTEAD OF CHIPS. I think that combination was possibly created in heaven, because DAMN. They are good.

If you decide to head into Michigan, there are some good outlets in Michigan City, Indiana along the way. Oh, and be prepared for the portion of the drive that will take you through Gary, IN - it smells like the world's most enormous, most rotten egg. Seriously, you might want to consider bringing a noseplug.

Elise says:

Other neighborhoods worth visiting are Roscoe village (Kitsch'n or Victory's banner for brunch, Piazza Bella Trattoria or Turquoise Cafe for dinner), or the Southport Corridor (more little boutiques and restaurants - take the brown line to Southport).

Also, the Museum of Science and Industry has a really cool exhibit on glass blowing right now as well that I totally think is worth checking out if you have time.

chirky says:

Roger went to university in Chicago, so I like to consider myself an expert on the city. I'm not, of course -- the only time I've spent there was the week of BlogHer last summer (Roger and I flew up a week early to frolic around the city, and wow: frolic we did. I had the blisters to prove it!). So anyway, these are my suggestions, that if I went back to Chicago today, these are the food places I'd return to without hesitation:

Garrett's Popcorn, DAILY, to feed (ha!) my caramel popcorn habit.

And then, obviously, you'll need to perform your own taste-test between Giordano's and Gino's East deep-dish pizza. I went thinking I was a die-hard Giordano's fan (A year or so before, I had mail-ordered one to surprise Roger, and it was sooooo good, though perhaps the most expensive pizza I’ve ever eaten, what with shipping costs and all), and came home a die-hard Gino's East fan. But that's a decision you'll have to make for yourself, and I won’t hold it against you if you choose Giordano’s because DAMN! They’re both good.

And then, one night when wandering around, we passed a Lebanese restaurant. It was closed, but looked so great that we made a mental note to go back the next day. We did, and we’re STILL talking about it. The restaurant is called Kan Zaman - it’s kind-of downtown, located near Wells and Ontario (Note: There's a Gino's East next door). Get the beef shish kabobs. Gah, that was maybe the most delicious meal we had the entire week – so perfectly tender and flavorful – and not expensive! And huge portions! Holly, the ambience of this place is perfect (hookah, low-lit beaded chandeliers, billowy draping cloths, and sunken, heavily-pillowed booths). There is a belly dancer if you go certain evenings (call ahead to find out when - perhaps on weekends). Go there. And oh! THE BAKLAVA. It was so good we ordered dessert ALL OVER AGAIN, just to get more of it. If you go nowhere else (except Garrett’s, and except to get deep-dish pizza), GO THERE.

chirky says:

Also, I feel compelled to make note of the fact that we taste-tested both Giordano's and Gino's East SEVERAL TIMES EACH throughout the trip. It was kind of an addiction. In fact, I think we survived on deep-dish pizza and Garrett's caramel popcorn.

Regarding touristy things, I'll have to think a little bit about that. I think one of my favorite things we did -- besides wandering around the city (I love wandering around cities) -- was a tour of Frank Lloyd Wright's home. Of course, Roger and I are HUGE fans of architecture (in general), so it was fascinating to learn about FLW and to see how his home was designed (timeless!). He designed several of the homes in his neighborhood, also, if you're craving a walking tour.

She Likes Purple says:

I have nothing really to offer. I've only been once and it was for, seriously, 36 hours. I will recommend the Banana Republic on Michigan Avenue because GOOD LORD it's the biggest BR I've ever been in. I also drove quickly past a champagne bar I would have just loved to stop at.

JennieB! says:

I can't believe no one said Avec or Blackbird...

if I could eat 1 meal in chicago - it would be one of those two places!

have fun
oh and my friend Ryan swears you should eat an Italian Beef when your there - I've never yet had one, but they seem to be like Philly Cheesesteaks...

http://en.wikipedia.org/wiki/Italian_beef

also - if you shop at the OG Marshall Fields it will feel like you're shopping in a grand museum - so lovely and old school.

jB!

Gwen says:

Yay! You'll love Chicago. Here's my suggestions for my home city:

Pizza - Pequod's Pizza (2207 N. Clybourn Ave.) It's all about the pan pizza & the caramelized cheese on the outside of the crust. YUM!

View - Signature Room/John Hancock (875 N. Michigan Ave.) Sure, you'll pay $10 for a cosmo, but that's the same price as the observation deck at either the Sears Tower or the Hancock. At least you can enjoy a unique view while enjoying a frosty beverage. Plus, the view from the women's restroom is the best in the city.

Neighborhood - Andersonville (Clark St. from Montrose to Peterson) This whole neighborhood is packed with goodies like wonderful design shops (Scout, White Attic), quirky bars (Hopleaf, Simon's, Konik's), wonderful bakeries (Swedish Bakery & Taste of Heaven), not to mention the Swedish-American Museum. This is my hood & it's totally worth the trip.

Anyway, I hope you two have a wonderful time. Go White Sox!!!!

FunnyGal KAT says:

My only Chicago experience is a trip to the top of the Sears Tower, so I'm no help there. But I wanted to say how considerate it is of you to warn Sean's future girlfriends of the quirks they'll be dealing with. It's got me thinking that perhaps I should write up a list of instructions for the Pretend Husband, maybe his likes and dislikes, how he likes his sandwiches cut, etc. So helpful for the next wife!

Janet says:

It's been at least a year since I've had a Diddy Riese cookie sandwich. Tragic, really.

Margot says:

While Cafe Ba-Ba Reeba IS tasty, it belongs to a restaurant corporation (Lettuce Entertain You) that specializes in big giant restaurants that feel a bit manufactured. So if you're interested in a more local, funky vibe, then Twist in Wrigleyville is charming and delicious option. There's also a lot of improv shows in that part of town, Improv Olympic has always been funny when ever I've gone.

Also, Orange for brunch is delightful. There are 3 locations and they all serve FRUIT SUSHI! Sooo adorable. Also you can custom order fresh-squeezed juices and smoothies and the menu changes weekly. OOH. Your post about candy reminds me in Roscoe Village there's a vintage-y candy shop called Suckers on Damen ave, which is walking distance from an Orange brunch spot.

Honestly, don't forget about the lake. If it's nice then I'd just say chuck it all and go hang out by the water. Rent bikes, walk, or grab a sandwich and drinks for a picnic.

HAVE FUN! :-)

Beth says:

Have Fun! I went to Chicago for the first time last summer for a wedding and I was SO excited. What did I see? Nordstroms and the Hyatt in Evanston. Awesome use of a plane ticket. And I know you can appreciate the significant markup on flights out of Charleston Airport.
The wedding was nice though, the bride wound things up by singing in the hotel bar with her dress thrown over her sholder to get it out of the way (and therefore shared her blue bridal undergraments with a few more than the groom).
:)

Tilly says:

Holy Hell you've gotten GREAT recommendations! And we do seriously love our city, no?!

In addition to what's been said, there is a great little breakfast place on Southport (Southport corridor, brown line stop) called Southport Grocery and it's little and you would have to get there early on the weekend, but OMG so good!

Also, if you are heading to Michigan, I would recommend Saugatuck. It's a little artsy, beach town about 2.5-3 hours drive (depending on how fast you drive and traffic) and I love it. My parents live there and I'm also getting married there in the fall. So, yeah. Super cute and quaint and not too far away. Actually, I will be there that weekend.

Have so much fun! No matter what you do!

missbeegail says:

I second Gwen that Andersonville is a great place for food and a little shopping. My two recommendations there are Hopleaf (http://www.hopleaf.com/) which is an awesome, awesome bar/restaurant that specializes in Belgian beer but honestly has one of the best all-around beer selections in city. And their food is good too. The mussels for two comes with fries and along with a few pints makes a fab meal. The steak frites is delish but GIANT. I recommend going on a weeknight if possible. It gets really crowded on the weekends. If you are just drinking the bar upstairs in open weekends only and is a place to escape the crush of the front bar. Also in that neighborhood is Taste of Heaven (http://chicago.citysearch.com/profile/3717389/) which is a fun place for brunch.

Oh, and several people have said this but if you want the view from up high, the Signature Room is a better bet than the Sears Tower because, hello, you also get booze.

I hope you have a great time!

Megan says:

Chicago! Chicago!

I'm too lazy to read anyone else's comments, so here are my suggestions, probably with some overlap:

1. Walk along the lake.
It's a nice long walk from downtown (cross Lake Shore Drive @ Chicago Ave. or Oak Street) to North Ave and back.

2. Lula Cafe (lulacafe.com)
Full disclosure: it's chock full of hipsters. But it'll get you out of downtown, into a neighborhood (Logan Square), and you can ride the subway there (catch the blue line downtown @ Clark & Lake, get off at Logan Sq., and the restaurant is right on the square). Easy.

3. Rosa's (rosaslounge.com)
If you want to see blues, I'd highly, greatly recommend Rosa's. It's not too far from Lula (by cab). Rosa's is owned by a guy named Tony, who, in his native Italy, met some Chicago blues musicians and then packed up and moved to Chicago to open his own place. It's named after his mom - mama Rosa! - who, to this day, I swear, STILL WORKS THE BAR. She's gotta be in her 70s. It's small and dark (and no smoking indoors anymore!) - a perfect setting to foster a good blues atmosphere.

3. Ride the brown line around the loop.
It's cheap and has great views of downtown, especially when you cross the river. Or ride it all the way to Kimball for more neighborhood views.

4. Chicago Cultural Center (www.flickr.com/search/?q=%22preston%20bradley%22&w=all) There's a really pretty ceiling in there. Used to be the old Chicago Public Library.

5. Millennium Park.

6. B'hai temple in Wilmette (http://www.flickr.com/search/?w=all&q=bhai+wilmette&m=text) You'd need a car for this one, but it's neat.

7. Architecture tour http://www.architecture.org/tours.aspx)
The one on the river is nice, but walking tours are cheaper.

Have a good time! I'll cross my fingers that the weather will be kind and obliging.

tina says:

lula. go to lula. www.lulacafe.com you won't regret it. it's where i eat my birthday dinner every year. and lots of other meals in between. i know it can be hard to get out of downtown when you are here visiting, but if you want to really see chicago it's best to get into the neighborhoods. i would second andersonville and bucktown, both mentioned above, and also lincoln square (my nieghborhood!) and logan square (where lula is). the weather here is ALWAYS tricky, so i'll keep my fingers crossed for you.

tina says:

ha! megan beat me to lula. and yes, she's right, be careful of the hipsters. sometimes they bite!

oh, and she's right about the b'hai temple as well. totally worth the trip.

andrea_jennine says:

I also nominate Giordano's over Gino's. Friends of ours who grew up in Chicago (as opposed to being a transplant like me) swear by Pizzeria Due (the original location of the Pizzeria Uno chain), but we haven't made it there yet. Other favorite food spots of mine are Julius Meinl (fabulous Austrian cafe in Wrigleyville), the Bourgeois Pig (coffeeshop) in Lincoln Park, and Tuscany (Italian food to die for; fabulous fresh pasta) in the Village/Little Italy.
Listen to the commenter to told you to visit the miniature room in the lower level of the Art Institute; it's really lovely. Millennium Park is right next door, lots of fun to stroll through. And if you have a nice day, rent some bikes and take the Lake Shore path (you can walk, too, you just won't get as far). There's also a boat tour of Chicago architecture that I've always wanted to try, but it can be a little hard to get tickets.
Oh, I almost forgot - day trips! Try Lake Geneva in Wisconsin and St. Josephine's in Michigan; both are charming. The Michigan dunes are fun, too.
I hope our Windy City isn't too windy for your visit!

E says:

If you do nothing else, foodwise, and you've already had pizza, GO TO Bistro 110: http://www.opentable.com/rest_profile.aspx?rid=2630
Right off Michigan Avenue and all the amazing shopping, the baked garlic app they bring to every table is aaaaaaaaaaaaaaaamazing. Five years later, I still have dreams of it. I live in New York and I'd walk back to Chicago for that place.

Also, though I'm opposed to Mexican outside of Texas, Frontera Grill (Rick Bayless' restaurant) http://www.fronterakitchens.com/restaurants/restaurants.html is awesome... pretty upscale and very good.

Megan says:

I just went back and read everyone's comments. I love Chicago.

Teej says:

Totally forgot about The Weiner's Circle! The Polish is to DIE for (with everything, plus grilled onions). But here's the deal: Their schtick is that the women who work the counter are very, very mean to some people -- particularly the really drunk idiots who show up late at night. And they say things to customers that would make George Carlin blush. But it's funny to observe. They wouldn't say anything to you because you're too sweet. (They never said anything mean to me in all of our visits, and the only things they said to The Mouse were suggestions that he, um, be their man, you could say.) Anyway, Katie's right -- if you go at a normal eating hour and not a drunk eating hour, you won't witness any funny dissing competitions. And really, the Polish is crazy good. (Get fries, too.)

I also echo the recommendations to go to Millennium Park! Totally forgot about that. The Bean is cool and the park is a nice place to walk around, provided the weather is nice.

Another good eating place is Tango Sur in Wrigleyville. Argentinean, BYOB, eat outside.

Finally, one place that we really like to go and get a drink is the bar in the Ralph Lauren restaurant, which is right next door to the giant Polo store on Michigan Ave. Especially if you can get the two leather chairs in front of the fireplace, shown here: http://rlrestaurant.ralphlauren.com/about.asp. (And we've gotten them multiple times, hasn't been too hard.) Super cozy spot.

rosalicious says:

Seeing as I will be in Chicago next week for work (first time visit), this is all so helpful for me too ;)

Megan says:

One more: if you're in town on a Thursday night and like this sort of thing, a taping of Wait Wait Don't Tell Me is fun.

http://www.npr.org/programs/waitwait/

shokufeh says:

I second (or third?) the Garrett's popcorn recommendations, as well as the Baha'i Temple in Wilmette (http://www.bahai.us/bahai-temple). Did anyone suggest Frank Lloyd Wright tours in Oak Park? To be honest, I never did it. But I did enjoy donuts at the Saturday morning Oak Park farmers' market.

Abigail says:

I'm totally going to bypass Chicago even though I grew up there because my memories are nothing compared to the expert advice already in these comments. For real, if I ever go back there and get to do something cool aside from family-related nausea, I'm taking suggestions from your readers.

ANYWAY.

I live in LA and I've only been to Diddy Reese a few times and it is so, so, amazing and I feel like a total douche when I hear you out-of-towners get all excited about it because for real, Abigail, you can't drive twenty minutes to get the best ice cream sandwich ever?

I can't recall you specifically requesting advice for other things to do in LA but those I can give you because I live here and I like to tell people what to do (so sue me). If you're into musicals (which I really hope you are) you should try to see Wicked Sat night. There are usually reasonably-priced tickets on eBay within 24 hours of a show. ALSO, there is a diner on Franklin, Cafe 101, that is delicious. They have sweet potato french fries and black eye milkshakes and waffle brownie sundaes and mac n cheese, and I could go ON AND ON. Also, every time I go there I see someone who has played a small part in one of the many TV shows I watch.

Am I still talking? Last but not least, if you want a Diddy Reese buddy who is not some sort of creepo stalker I SWEAR, I will meet you there and coo over your accent and your writing. See, I am so normal.

Erin says:

ohohoh, I loooove Chicago. I love it so much that I decided to get married there despite the fact that I live 5 hours away and have no family or ties there. I'll brainstorm on some cool places to go for you, but if you are looking for some good pizza, try Connies http://www.conniespizza.com/ We ate there for our wedding reception and it was scrumptious and ooohhhh soooooo cheeesy!

citywendy says:

You and Sean would love the Hopleaf in Andersonville. It gets crowded on Friday and Saturday nights, which could be great people-watching for you and a chance to maybe mingle with the locals, but if that doesn't appeal to you, get there around 5 PM or so for happy hour (though they don't do specials)and enjoy having most of the place to yourself.

citywendy says:

I second the Lula recommendation. Ira Glass says it's his favorite place in Chicago, so you don't have to take my word for it...

Brooke says:

Wow, you almost had me convinced Sean was perfect until that Yankee's thing...because I must say that a day at Fenway park, eating Fenway franks and drinking that $7.00 beer all while singing "Tessie" would make me a happy girl.

Have fun in the windy city.

Jenn says:

Holly, I've never been to Chicago, but I have had an amazing jewelry store bookmarked forever and I would love to live vicariously through you:
http://www.gemjewelryboutique.com/

Also, I think my BF and Sean are long lost Yankee brothers: every vacation we take is also planned around the Yankees schedule and he buys tickets in a three days of vacation to one game ratio. A week in Seattle? Two games. Same thing with San Fran this coming September. Sigh.

Have an amazing time!

bookgeekgirl says:

Oh yay! Chicago! I'm a little bit jealous, actually -- I lived there for a year and a half during grad school and I STILL miss it. San Francisco is lovely, and all, but Chicago felt way more like home to me. Anyway, my recs:

1. I'm going to jump in with the Gino's minority for pizza. I worked right around the corner from the one on Wells and, um, ate probably more of it that I'd like to admit. Yes, it's touristy and can be -crowded- but I like it WAY better than Giordano's. And the salad at Gino's is great, too. (y'know, if you actually decide to eat something green along with your heap 'o cheese).

2. If you want to do the view-of-the-city-from-a-high-building thing, my advice is to skip the Sears tower. Go to the Hancock on Michigan instead. Preferably at dusk or later. At the Sears, you'll pay 10 bucks just to get to the observation deck. At the Hancock, you can go to the bar,instead, one floor below the observation deck. It's free to get in and then you can use your $10 for a drink, instead. Plus, the view from the women's bathroom in the Hancock is AMAZING! My favorite view of the city, in fact.

3. I'll third or fourth or whatever the folks who suggested Wicker Park / Bucktown. That's where I lived, and it's a GREAT neighborhood. Toast is totally delicious and worth the wait for breakfast, if you ask me. The blueberry buckwheat pancakes are fabulous. Another good breakfast (or lunch) place in the neighborhood is Milk and Honey on Division, which also has all sorts of cute boutique-y kind of shopping. And if you still have room after breakfast, the pecan bar at Alliance Coffee shop is killer good. And for dinner in that neighborhood, I'm a big fan of Club Lucky. It's this old school Italian place, with red banquettes and the BEST eggplant parm and martinis (with blue cheese olives -- yum!). The Pontiac cafe does live-band karaoke, which is fun if you're into that sort of thing, but it's pretty full of hipsters. Also, my favorite bar in the area is The Charleston. It's back in a neighborhood, on Charleston street, not on the main drag. They have a pet cat that wanders about the bar and a goat head wearing a chef hat hanging on the wall. AND a really great jukebox. How can you go wrong?

4. The hotel you're staying at is very nice, but it's in an area that'll be pretty shut down at night, if I'm remembering right. When you're searching for a place for a late night drink, with some REAL Chicago character, check out the Billy Goat Tavern. It's underneath Michigan Ave, pretty close to the river, and it was the subject of a Saturday Night Live skit way back when (that cheezborger one). It's full of little old men and has, like, 2 choices of beer on tap (light and dark), but it's open till god-knows-when and it's a nice respite from the glitzy touristy stuff of Michigan Ave.

5. I highly recommend the Architecture Society's river cruises, if it's warm and not too windy when you're there. Really interesting views of the city, knowledgeable tour guides.

6. As for your road trip, Madison, WI is GREAT fun -- pretty college town, good brewpubs and outdoorsy stuff. And driving up the coast of the Lake through Indiana and into Michigan is a pretty drive (once you get past Gary -- STINKY!). You could go to Holland, MI or Grand Haven. In fact, it'll probably be a good time of year for the tulips in Holland.

Okay, I could spend ALL day reminiscing about my favorite Chicago places, but I should probably get back to work now. Have fun! Eat a hot dog and drink an overpriced beer for me at the Sox game!

Anne & May says:

Tell Sean that I know someone who is ALWAYS available for ball games. He'd be so happy not to have to say things like, "And that guy is called the batter. What? That stick in his hand? IT'S A BAT. GOD HELP YOU!

Caitlyn says:

I'm sure someone's already mentioned this (52 is a lot to read!) but isn't Chicago called the windy city because some reported referred to all of the "windy" politicians?

NothingButBonfires says:

Bookgeekgirl! Yes, Holland, Michigan is the town I'm supposed to be checking out for my parents! Did you know it was one of the top ten places to retire to last year?!

A different Gwen says:

Oooh, Holland Michigan is kind of funny, what with the Dutch windmills and the dancing clog girls. Saugutuck is one of the cooler towns between Chicago and Holland. I love Homer's ice cream off the main drag there.

I'm going to get all wacky and trumpet Lou Malnati's pizza, instead of the other G's. I think they've got the best tomato sauce, although the restaurant itself on Wells is a little bit ick. This makes it exactly like all the other pizza restaurants.

Bookgeekgirl and I could be pyschic twins because she has recommended great stuff, especially the Wicker Park 'hood (this season of Top Chef was filmed in Bucktown, if you are a fan of such things; Bucktown also hosted the Real World Chicago and the neighborhood denizens were so unhappy about it, they left a dead body outside the apartment. True story. If you walk by Piece (decent thin crust pizza) on North Avenue, the Real World apartment is across the street). She's also dead on about Hancock vs. Sears.

Seriously, if you take half the suggestions here, you'll have a great time in Chicago, although I would stay out of Lincoln Park, home to Ba-ba-Reeba (except to visit Lori's Shoes on Armitage, because that place is heaven). But that's just me.

And at Comiskey (I know, yes, it's actually called U.S. Cellular Field or some nonsense), make sure you get the grilled polish sausage and onions that are at the stand alone kiosks (you might have to walk a little way to find those, but if you are a hot dog sort of girl, it'll be worth it).

Have fun! April weather, like all Chicago weather, is iffy. Hope you get the good stuff.

Sheila says:

Holly, remember the cheese curd I promised? The DEEP FRIED cheese curds? You MUST come to Wisconsin. Our grass is just beginning to green up for you. Yes, Madison is great, but Milwaukee is closer. We've got the best Mexican food this side of the Rio Grande and lots of great brewpubs. Or! A brewery tour! Free samples! Our team's in town, too, playing the Florida Marlins. (I can get you half-price tickets!) If you decide Milwaukee is for you, email me and I'll give you some suggestions.

If, having seen all of Chicagoland, you want to get away from city viewing, I suggest a drive to Lake Geneva. You'll see lots of pretty farmland (plus also some GIANT homes) on the drive up from Chicago on HWY. 12/59 and Lake Geneva itself is old-timey and quaint. Taffy shops and ice cream parlours, etc.

Melanie says:

I second/third/whatever the recommendation for Cafe Iberico. It's on LaSalle, just south of Chicago Ave. Cafe Babareeba & Twist are good, but Iberico is or FAVORITE.

Another excellent breakfast/brunch place is Bongo Room on Milwaukee Ave in Bucktown. It's a couple blocks from the Milwaukee/Damen/North intersection and sooo good.

My husband and I left Chicago last winter after nine years and we find out today if we get to move back.

Have a great time!

Melanie says:

And I grew up 20 minutes north of Holland in Grand Haven!

Colleen says:

Since my blog is entirely about (ok, so not entirely) Chicago, I will point you there and at the same time tell you that this city is fabulous, and the weather of late has been FINALLY cooperating.

Check out a post I just wrote when my mom was in town, and it names a few places to check out: http://chicagocommutercommentary.blogspot.com/2008/03/my-kind-of-town.html

Have fun!

Emily says:

For pizza, can I recommend the Chicago Pizza and Oven Grinder? They make a pizza pot pie (think pizza in a bowl, crust on top) that needs to be seen (and eaten!) to be believed. You can check out their website, in advance, at http://www.chicagopizzaandovengrinder.com/menu.htm

Have fun!

Gwen says:

Bongo Room! Melanie, thank you. I couldn't remember the name of that place for anything but wanted to recommend it because it's so good.

Rebecca Faulkner says:

As an Oakland resident, I really feel I need to speak up here. I am engaged to a native Chicagoan with native Chicagoan parents, and ALL THREE of them agree that Zachary's deep dish pizza (from here in Oakland!) beats any deep dish they've had in Chicago. Really! According to them (and all the other Chicagoans I've met) Uno's is THE pizza to get in Chicago. But just remember, you should make the trip to Oakland one of these days and have some Zachary's! Maybe have it for lunch after your next trip to the Alameda flea market or something. It's next to Rockridge BART.

Rebecca Faulkner says:

^^ regarding this.

Um, maybe it was called Gino's, not Uno's. I can't remember! I like Zachary's too much.

andrea_jennine says:

Oh, oh, AND check out the Frank Lloyd Wright house in Oak Park (just west of the city).

If you go to Holland, it looks like you'll be a week too early for Tulip Time, but I'm sure the flowers will be in bloom already. Their site has information on area restaurants and attractions: http://www.tuliptime.com/area-info

erose says:

I glanced over some of the comments, and their recommendations are good, but a lot of what was suggested is very touristy (Michigan Ave. is loaded with tourists, and the shopping is all chains, so it isn't going to be a particularly unique experience)(by the way, I think I win your long sentence contest. Ha!) I'm not sure if anyone mentioned this, but you are not going to want to do any eating, shopping or walking around the ball park before or after the game. It is really not the best of neighborhoods and it doesn't really have anywhere to do those things. It is a pretty good ball park, though, so the game itself should be tons of fun.

As a native, here are my recommendations for some non-touristy places to eat, shop and drink. I live in Wicker Park (Northeast of downtown, $12 cab ride from your hotel, funky, artsy neighborhood) so I will keep my suggestions to the area I know best:

Shopping - Damen Ave. north of North Ave. has lots of fun boutiques, which I LOVE. Prices completely vary, so it is kind of hit or miss. Also, North Ave. has some good shopping. There is a store called Akira (it started as a single shop, but has been successful so it has opened lots of stores now) that has stores all over North Ave., just East of Damen. Each store has something different - mens' clothing, women's clothing, shoes. The shoes are a bit funky for my taste, but the men's and women's clothing stores are very cool. The women's clothing store is at North Ave. and Honore, and the men's store is on North just West of Wolcott (they are only a block apart). North Ave. and Damen also intersect with Milwaukee Ave. Milwaukee also has fun shops, South of the three way intersection. If you walk South on Damen Ave. for half a mile, you will meet Division. Go West on Division for some stores with cute things for the home. Also, there is a sandwich shop called Jerry's, which has the best freaking sandwiches in the whole wide world. They have a menu of 100 sandwiches (you can also build your own) and they also have an excellent beer selection.

Eating - I already started this with Jerry's sandwich shop. Other fun places to check out are Silver Cloud on Damen, north of North Ave. Their slogan is "food your mom would make if she got paid." They have great comfort food. Also on Damen is Coast, which has excellent sushi, but you probably don't need to come from San Francisco to the midwest to get sushi. So, moving right along... Feast is on Damen, also north of North Ave. and it has the most amazing brunch. It has lunch and dinner, too, but they aren't nearly as spectacular. On Milwaukee, southeast of the big intersection, you will find Bin Wine Cafe, which has tons of very tasty wines (they offer flights, which I enjoy). They also have an extensive cheese menu and do a wonderful job of putting a plate together for you, based upon what you are drinking. They have a very limited food menu (other than cheese) but everything they offer is divine. If you are looking for Italian food, Cafe Bionda is on Milwaukee, southeast of the big intersection. It is a very cute, cozy place and the food is wonderful.

Drinking - My current favorite place to drink in Wicker Park is Violet Hour. It is on Damen, about a block south of the big intersection. It is set up like a Prohibition Era speakeasy. There aren't any signs for the place, but you will know it by the small yellow light above the door and the very well dressed bouncer standing outside. They aren't as pretentious as they sound, though. The drinks are all prohibition era recipes and they are out of this world. They have different shaped ice for different drinks, to give you an idea of how specialized each drink is. They are expensive ($12 per drink) but they taste amazing, are really unique, and very strong.

A couple of other notes (I'm now going for the Longest Comment Award):

Deep dish pizza - there are two kinds of "deep" pizzas in Chicago. True deep dish has a very thick almost bread like crust. I agree with a previous poster that Pequods at Webster and Clybourn is the best in the city. There is also stuffed pizza, which has a thin crust but has several inches of cheese. I prefer Giordano's or Uno's for this kind of pizza. Either way, bring pants with an elastic waistband.
Tapas - There are several tapas restaurants in this city, and some are better than others. You will probably want to avoid chainse like Ba BA Reeba and Emilio's. My favorite is 1492, which isn't too far from your hotel. The address is 42 E. Superior.

Other fun places near your hotel: Pops for Champagne at 601 N. State Street and Quartino's at 626 N. State Street.

If you like Greek food, head to Greek Town, which is on Halsted, around Adams. My favorite restaurant there is Pegasus, which is at 130 S. Halsted.

A good resource for ideas, reviews, etc. is www.metromix.com.

I have written way too much here. I'm going to stop typing now. Enjoy your stay!

Adele says:

"Future girlfriends of Sean"?

As if any one could match up to your good self!

Sean would surely be in folly if he ever gave up on Holly.

(thank you, I too will be here all night)

(LOVE Chicago. Jealous. But am going to Vancouver Island for 10 days soon...so that'll do!)

NothingButBonfires says:

Whoa, I have to just thank everyone for these AMAZING suggestions so far. A million thank yous! Having 67 personal tour guides beats the PANTS off having a dog-eared copy of the Lonely Planet, that's for sure. Thank you!

Lindsay says:

Should you decide to try the Wisconsin side trip, I should probably let you know about a little thing called the Mars Cheese Castle, whose exit I don't remember but it's only a few miles across the border on I-94 and you can absolutely see it from the highway.

It's so good, residents of Kenosha don't even get tired of it. As a former resident of Kenosha, I miss it with a large portion of my taste buds. And! I believe the Little Europe restaurant, also off I-94 in Kenosha, is the restaurant with the real grass roof upon which happy sheep frolic and play.

Marcy says:

I second the art institute and would like to add the Museum of Contemporary Art. I have all of the same recommendations for food and shopping but would like to add that Pilson is a great little neighborhood if you're wanting some authentic mexican on the cheap. They encourage you to bring in your own beer, so we usually pick up a six pack of Old Style and take our time over dinner.

I'm an Ann Arbor resident, so I would say COME HERE! Ann Arbor is a great MI stop for food, music and artsy shopping, but may be too far east for 1-2 day trip. South Haven and Saugatuck are both neat little towns, and I enjoy them both much more than Holland, which is a little too conservative and bland for my liking. If you find yourself in Kalamazoo you should stop in for a summer citrus Oberon ale at Bell's. The Everyday People Cafe (in Douglas, right by Saugatuck) has lovely food. Uncommon Grounds (also in Saugatuck) is great for coffee and usually has live entertainment. All of the State Parks along the lakeshore are beautiful, and great if you feel like taking in the lake and dunes without all of the noise and people.

stefanie says:

Hi Holly-
Well, you are certainly lucky with your timing- we've had CRAZY cold weather- just last saturday it SNOWED. -Seriously. It MUST be over now.

Anyway, my two cents are these:
1. FOR SURE giordano's over gino's.
2. My favorite restaurant is called Noon-o-Kebab, its persian food- highly recommended by local old-school persians (aka my dad and his friends) its on Kedzie (you can take the brown line, it also stops in lincoln square, where my favorite bag-buying store is- Secret Closet- if you go to LincSq also eat at Boca dela Veritas- HOMEMADE toretellini and limoncella- YU-UM!)
3. Andersonville is great too, the Hopleaf on Clark Ave for mussels and beer (SO MANY kinds of imported beer- check the website)
4. I'd say places like cafe baba-reba and Japonais are quite trendy- but as you can see my tastes are very local.
5. If you're into international/ music check out The Old Town School of Folk Music (on Lincoln in lincoln square) or the HotHouse (my personal favorite organization- a nfp org which bring international music to chicago) they just moved into their new home (again, check website hothouse.net)
6.I'm a city girl, so I have no clue about Holland MI, but it you can get there via boat (is that crazy?) it may be nicer, cuz driving thru Gary, Indiana is gross (sorry garyians)

Good luck, have fun & Welcome to Chicago!

Camels & Chocolate says:

Top Chef is in Chicago this season! Perhaps you should turn to it for dining advice? http://www.bravotv.com/Top_Chef/season/4/about/index.php

Also, be glad you have a sports-obsessed boyfriend versus one who turns and looks at you blankly when you talk about how the SEC is the hardest conference in both football and basketball. "Conference, what's a conference?" he blinks stupidly, and you know you can never tell your father this for fear he will turn down the boy without hesitation should he ever ask for your hand in marriage.

NothingButBonfires says:

Okay, now I'm seriously intrigued by Gary, Indiana. Why does it smell so bad?

Kirsten says:

I can't help at all with hints for Chicago, but it seems you have that covered from all the previous comments. (Note to self - get back to Chicago.)

For fun roadtripping places that one must visit, I recommend taking a look at www.roadsideamerica.com (it has the Mars Cheese Castle on it, among many many other things). It lists attractions by name, city, and state so its pretty easy to find things.

Gabbiana says:

I went to college in Chicago. In my four years there, the weather did not get truly warm until June. April is a toss-up: Some nice weekends, but it can also snow. If you're going to spend a few hours sitting immobile in a shady stadium fully exposed to the wind, you'll want a few extra layers. And by "a few" I mean at least three.

I can't believe no one has mentioned the Neo-Futurists and Too Much Light Makes the Baby Go Blind (http://www.neofuturists.org/). Constantly changing, touching, clever. And cheap!

Which leads me to say: Chicago is a great comedy and theater town. Definitely make it over to Second City. See what's playing at the Steppenwolf or any of the big places down in the Loop. Or pick up a copy of the Chicago Reader (http://www.chicagoreader.com/) when you hit the city. It's free, it's everywhere, and it's got listings and reviews for all the small cheap shows that are usually terrible but occasionally fantastic.

I disagree with some of the above in that I hate, hate, hate Navy Pier. Too touristy, too expensive, not much to do unless you are five years old. And I thought Bistro 110 was kind of overrated. All of that said, it has been three years. Moving on.

Chicago Cultural Center: Like someone already wrote, great ceiling, free exhibits. And just across the street from Grant Park and the Art Museum and maybe the bean.

Art Institute / Museum of Contemporary Art / Terra Museum of American Art: Yessss.

If you make it down to Hyde Park (... but why would you?), the campus of the University of Chicago (woo! go Maroons!) is pretty and also right up next to Frank Lloyd Wright's Robie House. And the Museum of Science and Industry isn't far, either. (I like the MSI better than the Field Museum or the Shedd Aquarium.) Then pick up a bucket of wings from Harold's Chicken Shack and a bucket of ribs from Ribs n' Bibs down the street. Congratulations! You are officially me in college.

Places to eat: Gibson's for steak (and the strawberry shortcake dessert, oh god), Triple Crown for Chinese, Giordano's for pizza, Roditys for Greek, Cafe Spiaggia (close to your hotel) for Italian. Also: Cafe Absinthe, Cousin's, Feast. Oberweis for ice cream.

Have fun, Holly. I'm jealous as hell.

sarah Lawrence says:

Everyone here has great recommendations, but I do feel the need to correct the person who said Super Dawg was in the suburbs, since it is my former neighborhood - it's right in the Bucktown/Wicker Park area (a neighborhood of Chicago), so you can check out all the other great things to do in Bucktown/Wicker Park AND enjoy a hot dog (no mustard!)! Coast on Damen (just north of Armitage) is the best sushi restaurant in Chicago in my opinion, possibly because it was just right across the street from me when I lived there. And it's BYOB, which is always fun in my opinion - bring a bottle of wine from the nicest 7 Eleven ever across the street, they actually have a pretty decent selection! Other restaurants and bars in the Damen/Armitage area include Rio's d'Sudamerica (Argentinian), Cafe Laguardia (Cuban - GREAT nachos, made with plantain chips!), the Map Room (Belgian beer bar, amazing selection, great atmosphere, possibly the bar I miss most), and Danny's (an old house converted into a bar, lots of character. And the walls are painted plaid!)

Enjoy your trip, I'm so jealous!!

Sarah says:

Oh, and also, I went to my first Cubs game every in April, and it was freezing. The day before and the day after were in the 70s, but the day I went to the game, it barely broke 40. Just something to keep in mind!

tina says:

holly,

gary, indiana, is a steel mill town. that's why it smells. it's a place that was once quite prosperous, but it has suffered greatly in the same ways that most industrial towns in the u.s. have. if you are interested in architecture, especially the industrial and/or abandoned kind, it can be a beautiful place to visit, but yes, it can also be stinky. for your purposes, if you drive through, which you will if you go to michigan, you should just make sure to turn on what we call 'the gary filter', that little knob that changes the fan from outside air to inside air. oh, and one of gary's main claims to fame is that michael jackson grew up there. so there's that. :)

whoorl says:

Chicago! I second everything Teej said, but don't forget my old stomping grounds, Bucktown and Wicker Park.

And Huntington Beach? DO YOU KNOW HOW CLOSE WE WILL BE TO ONE ANOTHER?!

Anne says:

I tried to post this last night but it didn't go through...
We just found out we will be taking a trip to Chicago in late October! I'm so excited since I have never been and the food just has me drooling already:) Can anyone tell me what the weather might be like around the last week of October? Also we'll have 2 of our kids with us, ages 9 and 12. My daughter(9) of course wants to go to the American Girl store but does anyone have any must do ideas for kids that age? Touristy is fine but I'll be on my own with the kids while my husband attends a conference part of the time so I don't want to travel too far- I think he said we'll be staying near the magnificent mile area??
Thanks for all the great ideas already- I am getting more and more excited!

Leanne says:

I love your blog but this is my first time commenting! I've lived in Chicago my whole life and while I love downtown, I also love the neighborhoods. I live on the NW side. Food: Chicago-style hot dogs, deep-dish PIZZA, Italian beef. Greektown, in the West Loop, is a fun location for dinner. The Billy Goat Tavern is a Chicago legend thanks to the SNL skit..."cheezeborger, no fries -- chips." I love the TV program, "Check Please!" on the local PBS station. The concept: three everyday people, from anywhere in the greater Chicago area, sit down with a host to discuss three eating establishments, one favorite chosen by each guest. You can check the website for recommendations!! Andersonville (on the north side/ red line trains) is a fun Swedish neighborhood with several theaters if that's your thing. Ravenswood and Lincoln Square (north side/ brown line trains) have a wonderful European feel. And the Wicker Park/Bucktown/Ukrainian Village neighborhoods (west side/ blue line) have some great artist galleries, coffee houses, book stores, neat shops, etc.

The Chicago Cultural Center is located on Michigan Avenue across the street from Millennium Park. The park is a MUST SEE!!! There are free rotating art exhibits, music programs, the world's largest Tiffany stain-glass dome, bathrooms AND an information center at the Cultural Center. You can get a lot of free and/or discount coupons for city restaurants and sites. The Hancock Observatory on N. Michigan Ave. is great and I think better than the Sears Tower. The Art Institute and the Field Museum are both better than Science and Industry. In my opinion, Science and Industry has gone down hill over the years and it's a little dumpy. But the U-505 Submarine exhibit (new! improved!) is great! I would highly recommend the Edward Hopper and the Winslow Homer exhibit currently at the Art Institute- wonderful! The Redmoon Theater specializes in high profile and unique productions using both human actors and puppets. Second City and the Neo-Futurists are good picks, too! I love the Old Town School of Folk Music in Lincoln Square- see what's playing. The Chicago Architecture Tours offer both boat tours and walking tours- very enjoyable. Take a walk in Lincoln Park. Walk along the lakeshore.

Have a wonderful trip!

bookgeekgirl says:

Someone already answered your question about why Gary smells so godawful, but I wanted to add that you should keep an eye out for the flaming smokestacks as you drive through. Someone once told me that they flame like that to burn off chemicals that are released into the air by the manufacturing. I don't know if that's true, but I'm fairly certain that I am someday going to have babies with extra arms or 5 eyes from having driven through Gary so many times on my way to my folks' house in Michigan. (Yet at the same time, something about the flaming smokestacks fascinates me and reminds me of the Lord of the Rings movies, when the orcs are preparing for war. But maybe that's just me :-)

Also, I've mostly agreed with all the great recommendations folks have given you. However, I'd say skip the sushi. Coast is pretty good, but can't compare to what you get on the West Coast. The 1st time I had sushi out here after moving from the midwest, I was like "OH, this is what it's supposed to taste like!"

emily says:

I just sent you an email with a ton of stuff, and also offering up my car and tour guide services for things you might not get to see downtown. Really, I'm serious - let me know!

Nancy says:

Wow, I have to admit I am eagerly cribbing from these comments for personal gain since, weird as this is, Dakin and I too are going to Chicago next weekend as a little get-away (the 25-28th).

(which, um, hey!?)

The restaurant that I can remember loving from a trip a couple years ago is called Blackbird -- a bit arch, but the food is delectable. Frankly, all I can think about now is PIZZA.

erose says:

Anne,

In late October, it is usually cool and rainy in Chicago. As for things to do with kids, Navy Pier is a great place to entertain them for the day. In late October, they will have the Navy Pier Fright Fest, which is a Halloween themed event for families. They have shows, rides, face painting, haunted houses and other fun things. I took my 7 year old niece last year and she loved it. They have different activities for different age groups, so your 12 year-old daughter will find things she likes as well. Navy Pier also has the Children's Museum, which is the best way to occupy and exhaust kids for an afternoon. They are talking about moving the Children's Museum to Grant Park, so definitely check with your hotel to find out if it has been moved before you plan to go.

If the weather cooperates, Millennium Park is lovely. So is Lincoln Park, which is home to the Lincoln Park Zoo.

The Museum of Science and Industry is very cool and has more stuff that kids enjoy than other museums do.

I hope this helps. Have a great time!

Melissa says:

Wow! I can't believe that no one mentioned the coincidence that you are going to be here the EXACT weekend that the the largest international art show in the world will be going on in Chicago! Lucky you: http://www.artropolischicago.com/

I work in the merchandise mart and have been watching them set up for the past few weeks. I've been excited about this show since I went last year.

Yes, the Art Institute is fantastic - but this is an event made up of 5 very different shows (contemporary, modern, antiques, ect.) that bring an rare collection of artist together. I really recommend checking this out :)

Maren says:

Ok, I know Sheila promised deep fried cheese curds, but I can do one better and provide that AND cheese curds fresh out of the vat - squeaky squeaky! Or if you decide to go to Michigan to help your mom (yawn) you could always come back in September for Cheese Days...A whole weekend devoted to cheese! What could be better? http://www.cheesedays.com/

Anne says:

Thanks erose! My 12 yr old is actually a boy so I'd like to find something cool for him as well. You had some great suggestions- the Halloween thing sounds great and I know he'd like the Science museum too. Thanks so much!

Clea says:

In the South Loop, around 800 S Wabash, try Canadie Le Chocolatier. They have best truffles and gelato I have ever tasted, even in Italy.

Elle says:

I can't recommend Yolk highly enough for breakfast -- amazing. It's in the South Loop, on Michigan around 11th. The cinnamon roll french toast? Like heaven on a plate. Have a great time!!

Daily Tragedies says:

I figure with 92 comments, somebody's told you where to eat pizza. Instead, I will tell you to take your baseball-loving boyfriend and steak-loving self to Harry Carey's Italian Steakhouse & Bar (colloquially known simply as Harry Carey's). Eat the fillet. Trust the chef on medium rare. You can't go wrong.

ladybug613 says:

You should definitely take a trip to Milwaukee. As mentioned before, the Milwaukee Art Museum is a must see. You should also stop in Bay View (a part of Milwaukee that has cute stores and fun restaurants) and try Cafe Lulu on KK and Lincoln. They have the best Asian slaw and potatoes with blue cheese dipping sauce. You should also visit the 3rd ward for more fun shopping. Have fun in Chicago and come to Milwaukee!

Becky says:

I'm from Rockford, Illinois, which is about 90 miles northwest of Chicago (we're not a suburb, nor are we a farm town...it's a legitimate city! people don't usually believe this). If you are heading into WI and taking 90, you will pass through Rockford and I would recommend a stop there. The exit area has a lot of food options (mostly chains in that area, so you'll know what's what) and it's fairly easy to get on and off.

Chicago has WONDERFUL museums. I'm glad to hear you're planning on visiting the Art Institute, which is fabulous. I also love the Shedd Aquarium (then again, I'm a marine biologist) and the Museum of Science and Industry.

April should be mild, but the midwest has very unpredictable weather so bring a few layers if you can and definitely check the weather before you leave. And YES it really will be windy.

Have a fun trip!

Carrie says:

Highly recommend western Michigan. The sand dunes along the lake (especially as you get farther north) are pretty fantastic.

marissa says:

I totally agree - go to the Top of the Cock (hee heee heeeee!!) for drinks at the Signature Room (John Hancock building). Scary elevator ride, but the view is incredible. At night it's breathtaking. Uno is great for deep dish too!

I love Chicago, enjoy!

Aparna says:

Hey Holly,

You had some great suggestions for me when I visited San Francisco so I'm so happy to be able to return the favour -- though with 97 comments already, you really don't need it (but I'm taking note of all the places I haven't tried yet!)

Someone already recommended Hot Chocolate in Wicker Park and I just wanted to add that if you go there, don't be fooled by the name into thinking that you should only have dessert, because their main courses are pretty damn amazing too. Try the mac and cheese. It's the best I've ever had in my life, and normally I don't even like mac and cheese so that's saying a lot.

Also try Earwax Cafe in the same neighbourhood, their chocolate chip buttermilk pancakes are out of this world. The Bongo Room down the road is overall better for a sinfully sweet brunch (such as chocolate french toast with banana creme brulee) so if you want a whole lot of options for your sweet tooth, go there. But if you're just in the area and feel like eating, Earwax is open until midnight most days so I would stop by just for those pancakes.

Wicker Park/Bucktown is one of my favourite neighbourhoods in the world -- nowhere else has such a perfect combination of tattoo parlours, psychics, hipsters, cute boutiques and an insane variety of affordable gastronomic temptations. Also I need to second the Akira recommendation someone made: there are about 4 stores down North Ave, and they're like a cheaper, trendier version of Zara.

I just have one suggestion in a different neighbourhood: if you're going to see a Second City show in Oldtown, you must have dinner next door at the Adobo Grill. They make their guacamole fresh at your table, it's so good I could make a whole meal just out of that.

Have a great time in Chicago! It's a foodie's dream (I would say it's better than Singapore apart from the lack of good Indian food), you're going to love it. I'm currently eating my way through Europe but I miss Chicago madly, so please hit up some good places and then blog all about it :)

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