Chicago...
Art Institute of Chicago
Shedd Aquarium
Field Museum
Go see The Bean
more music and shows then you can shake a stick at.
See if you can get in to a taping of Wait Wait Don't tell me.

I went to Chicago this fall for a family vacation long weekend and had a wonderful time.

Definitely see The Bean, it is stunning, and there are a lot of other cool sculptures nearby. And the Art Institute is a must see also, but they are doing some construction and not all the galleries are open.

I would pass on the Shedd Aquarium due to high cost and high crowds. Also, avoid Navy Pier at all costs-- its basically a huge crowded shopping mall with no stores.

I highly recommend the Museum of Science and Industry, which is near the University of Chicago. They have a Nazi U-boat on display-- not a model or a piece of one, but a whole freakin' u-boat.

As for eating, don't leave the city without a Chicago style hotdog from a street vendor: pickle spear, tomato/onion/pepper relish, mustard and celery salt. Best hotdog ever.

I love Chicago, I go there for business a lot. I agree with what Edgeways and Drifter recommend and don't recommend, though I took a boat cruise or two, and those leave from Navy Pier and are a lot of fun. I like Chicago's funky neighborhoods -- Wicker Park is really cool, and so are Bucktown and Pilsen. I like the restaurants in Andersonville. There's an art district, it's west of the Mag Mile, a friend of mine owns a gallery there, Vale Craft Gallery, it's on W. Superior, along with the other galleries. The Zoo is amazing, and just fun to walk around. If you are a night life kind of person, Rush St. is fun. And, touristy though they may be, I like those blues clubs around there, I've heard some great music there. If you like Asian, Opera in the Loop is really good. Reza's is good Persian, Russian Tea Time is also great. I wish I could remember this Italian place that's great, but I can't. If you have time to see a play, theatre there is awesome and the tix are much cheaper for better seats than Broadway. And do check out the Bean, it is way cool, I love Millennium Park. Have fun.

Quimby's Bookstore, Wicker Park. Greatest and most subversive bookstore in the free world.

I have to second the Museum of Science and Industry as a top pick--I went there on a trip with my high school marching band back in the day, and it was the overwhelming favorite of the trip (beating out the art museum and the aquarium, amongst other things).

The only other thing I still clearly remember from that trip is that they arranged for us all to have a group meal at the "Rock & Roll McDonalds" downtown, and me & my nerd friends singing the Wesley Willis song by that name ad nauseum.

i'm from there and well-acquainted.

the first thing you should do when you get there is get a copy of the Chicago Reader and spend some time perusing for things to do. (also online

i second the passing on the Shedd unless you are *really* into fish--it's super expensive, and i'm sorry but after awhile they start to look the same. Navy Pier is only good for the ferris wheel, and that is way overpriced.

the Art Institute is awesome, and one day or eve is free (maybe Monday? check this out) Field Museum if you like dinosaurs. and Science and Industry if you've got kids or you're way geeky that way. (otherwise, i'd pass.)

The Bean and Millenium Park are a good thing to take in during your jaunt to the Art Institute, but it's not nearly so interesting in the winter.

Wicker Park is the new Lincoln Park, and so gentrified into nice funky stores and cool restaurants. (i miss the old days, but i still go there anyway.) you can take the el from wherever you're staying--the one toward O'hare. i like the EarWax Café, but most people find the service rude and indifferent. Quimby's is awesome if you're into comix. and there are funky little art galleries along thereabouts too. a Lucy Parsons memorial in the park itself.

i wouldn't recommend Rush St. unless you like a certain flavor of young, suburban drunk. better to find outlier (not downtown) bars that are featuring something that interests you in the music department. don't leave anything you like in your car, if you're driving. the el's always a better bet, since parking is a pain in the ass.

Too Much Light Makes the Baby Go Blind is a fun and cheap theatre experience, if they're still doing their thing.

You could take the tour at the sears tower,(tallest building in the US, and stunning on a clear day.) Then I took the nearby train to wicker park for a hotdog, record stores, etc.which was fun.

If you are going to check out bookstores, go visit my friends at Women & Children First, in Andersonville. 57th St. Books and Seminary Books in Hyde Park. Do you like Mexican, there's a great couple of restaurants, one of them is more casual than the other -- Topolampo (sp?) is one and Frontera is the other. I agree with hbh, check out the Chicago Reader for suggestions, that's a good resource. I'll have to ask my friend there for the name of the pizza place he took me to -- it's in Lincoln Pk and the pizza there is the best. Not touristy either, like the places near the Mag Mile. Probably too cold this time of year, but lots of bike paths in Chicago. . .

Cultural Center across from the Millennium Park is pretty interesting, as is the Chicago Historical society, north of the Mag Mile, I enjoyed both, and learned a lot about the history of Chicago at both places. And the Sears Tower is indeed cool, they have some interesting historical displays we really liked. I also just like walking around, looking at the architecture.

I just moved from Chicago after living on the north side for 10 years. The key, I think, is checking out the neighborhoods. Most of the stuff in the loop and on the museum campus that has been mentioned is great, but in my experience the heart of Chicago lies elsewhere.

Here are five of the things I miss the most - all easy recomendations -

Check out the Mexican Fine Arts Center in Pilsen - an amazing place with a great gift-shop.

Much of the north side of the city was home to German immigrants, and some of it still is. That flavor fades every year, but it is still there. Check out Lincoln Square - the historic hub of German Chicago. There is a great block to walk in the center of the neighborhood and several cool old German bars, alongside some good indie record stores and coffee shops. The best German bar in the city, though is a few blocks southeast of Lincoln Square, "Laschetts" on Irving Park, 1/2 a block west of Irving and Addison on the south side of the street. If the Anchor were in a German urban neighborhood it would be Laschetts - a truly special place.

The Mexican food in Chicago is amazing! The Rick Bayless places mentioned above are good (but super-pricey!) try one of the little tacquerias in Pilsen, or if you're on the north side check out "Tortas USA" on Ashland, one block south of the Ashland/Lincoln intersection. That place has the best burrito in the world.

If you're into Polish food, there are so many good little spots! The best is probably Bobak's Sausage company on the south side at Archer and Pulaski. It isn't really "little" but the food is just great (and cheap).

Finally, for a rock show be sure not to miss the Empty Bottle. It will feel like the Triple Rock or Turf Club in the cities, same kind of place with a lot of good local bands, cheap cheap beer and great site-lines.

Have fun!

American Girl Doll Store, Levis Store, Dunkin Donuts, Apple store...just kiddin

Seriously, I'd take a day and just walk. There are street performers on Michigan, we walked up to Second City (somewhere north of DT) to see a show and were amazed at all the little restaurants, shops etc. And those residential streets up that way are beautiful. A friend took me to a restauraunt R. Grunts? - supposedly the restaurant that invented the all-you-can-eat salad bar. It was good.
There was a photo gallery across from Mill. Park and maybe a little south on Michigan where I saw a GREAT show. Can't remember the name of it though. There's some cool stuff right around Mill. Park.
Avoid Navy Pier.
Ride the train somewhere.

About a year and half ago, Levy Home Entertainment sponsored a "Romance Authors K-Mart Tour," where 14 romance authors would tool around Chicagoland and then over to Detroit for 3 or 4 days, stopping at K-mart stores and signing books for K-mart shoppers. My editors sent me along to write a story on this. I spent one day with the romance authors on the bus, as I refused to spend more than one day on a bus, when I could be going to the Minny State Fair instead with my kid. We visited K-Marts all over Chicagoland, to the west and the south of the city. I actually had more fun than I thought I would, and ate very well, thanks to Levy. So, RachL, if you run out of things to do, there's always doing a K-Mart tour, I could give you some recs.
Seriously, if you check out Lincoln Sq, per Matt's suggestion, a great little bookstore there is the Book Cellar, they have a wine bar too. Books and wine, what more could you need?

One of the more unique and memorable experiences I've had in Chicago was an evening show at The Playground Theatre. It was cheap and very funny — be sure to BYOB for the full effect!

I live here in Chicago. Let me know if you want to see Blue Man Group-I can get probably get you tickets. I also have some free passes to the Museum of Science and Industry.

plus its fun hearing the suggestions on where to go since I live here. I love trying new places!

I love the shop Scout in Andersonville. It has great vintage home furnisings.

Two things: I've been to a couple of shows at Piven Theater, and it's great. The place where Jeremy Piven got started, owned by his family. Be forewarned, this and the other are nowhere near downtown. The second, and I'd highly recommend, is this weird ice cream place made famous because it was visited by the Beatles. I have no idea where it is and can't remember what it was called, but it was great, and if I were going I would definitely take the time to google it.

I love Chicago. Second only to Duluth.

boystown!!!

Don't forget to visit U.S.Cellular Field, home of the 2005 World Champion White Sox!

hey, i'm a duluth native and have lived in chicago for over 6 years now. this time of year isn't quite as busy as the rest but there is still a lot to do. i would agree that you should pick up a copy of the chicago reader, or visit them online. they are similar to city pages, and have critics' picks for music, film, and art.

i would second the art institute of chicago (no longer has a free day, only thursday evenings) and add the museum of contemporary art: it feels a lot like the walker (free on tuesdays). i agree that a trip to visit millennium park is worthwhile. the cloud gate, commonly known as the bean, is amazing in the right conditions. i love to go there early in the morning when few people are around and take the view in. they also have an outdoor skating rink that stays frozen regardless of the air temperature, great for days like today. and the bandshell there is designed by frank gehry. the architecture center is near there, if you want a guided tour by knowledgeable docents. navy pier is basically a glorified mall, but they do have a cool museum of stained glass that a lot of people miss. and the children's museum there is good for the little ones. a lot of locals prefer the view from the john hancock building over the sears tower. it is only a few stories shorter, but closer to the edge of lake michigan, so you can look north up the coastline. when i have friends from out of town, i will usually eat out someplace and take them for drinks at the lounge on the 96th floor. there is no cover, other than the cost of the drinks. also downtown is the gene siskel film center showing movies you won't see anywhere else.

away from downtown, the bucktown/wicker park area has greatly gentrified, thanks in part to me, but still has great places to visit. i live just a few blocks from the empty bottle and must say, as a music freak, that it is one of my favorite places in the world. the restaurant next door, called bite, has a great, veggie friendly, menu. reckless records is near the blue line, across from earwax, and features a fetus-sized indie music collection. i wouldn't miss the turtle sunday's at margie's candies for anything, worth any wait. the aforementioned quimby's has all the zines you could hope for, type of place that carries zak sally's stuff.

outside of that neighborhood, and that no one has mentioned yet, is the tours of the frank lloyd wright home and studio in oak park (easily accessed by the green line), the garfield conservatory (stay warm on a cold day, love the cactus room), the baji temple (open to the public), and (last but not least) hopleaf in andersonville. hopleaf has a huge selection of imported belgium beers and great food too. if there is anything that sounds interesting, let me know and i'll elaborate.

one more thing. you'll miss it by a week, but they might have it started by the time you get here.

www.museumofmodernice.com

Billy Goat Tavern (as depicted on the SNL 'cheeburger cheeburger' skit); 10 pin, the swankest bowling lanes I've ever been to http://www.centerstagechicago.com/bars/10pin.html; the Fermilab in Naperville; and any malls or chain restraunts in the suburbs ;)

Thanks everyone, you were all very helpful. I'll be sure to check some of these places out!