Anything there we shouldn’t miss? My husband’s been before, so he’s got some ideas about what he wants to show me, but in your opinion, what are the two or three must-sees?
What time of year?
Millennium Park is lovely, but the Crown Fountain is awesome when it’s on in the warmer months. “The Bean” (Cloud Gate) is neat too.
Skip the Sears - sorry, Willis - Tower unless you really want to walk out on the glass platform to overlook the city. To avoid a ticket price, long wait, and security screening, go instead on a clear day or night to the Hancock Building, take the (free) elevator up to the lounge, order a drink, and look out over the city.
Agreed on the Hancock vs. Willis observation decks, and on the Art Institute.
Don’t bother with Navy Pier, unless you very much want to feel touristy. It really is an overpriced tourist trap.
We have a lot of very good museums. Depending on where your interests lie, in addition to the Art Institute, you may want to see the Field Museum of Natural History, the Shedd Aquarium, the Adler Planetarium, the Museum of Science and Industry, the Museum of Contemporary Art (and that’s just the big museums). Note that the Field, Shedd, and Adler are all essentially “next door” to one another.
Then, there’s another entire discussion that one could get into on Chicago restaurants. 
Others will, I’m sure, soon chime in with the usual Field Museum, Museum of Science and Industry (avoid the U-505 if you’re in any way claustrophobic), Art Institute examples.
When I last went, one of the most memorable places for me was the Smith Museum of Stained Glass Windows on the Navy Pier. Then again, I’m a sucker for that sort of thing. It’s free, IIRC, unlike most everything else at Navy Pier. Lyric Opera of Chicago is a wonderful company, as you’d probably expect. The space is gorgeous, in a 30’s WPA sort of way, as many Chicago building interiors are.
I was going to recommend Sam’s Wine and Spirits, if you were interested in finding any unusual beer or wine, but it looks like they’ve been bought out by Binny’s Beverages. No idea if their previous fantastic selection and prices have changed in any way.
Goose Island Beer Company has a tasty microbrewery/pub with at least one location on Clybourn. I’m a giant fan of the restaurant Everest, but Chicago certainly doesn’t lack for great restaurants.
Last time I was there, I did a tour of the Frank Lloyd Wright home and studioand really liked it. (YMMV depending on your view of architecture). I personally just love wondering downtown and seeing the architecture, including the Chicago Tribune’s building with its little pieces of buildings from around the world. Then there’s also the Mag Mile for shopping…
In about three weeks, so well within the “freeze your ass off” season, though we’ll miss the Crown Fountain. I definitely want to see The Bean!
The Art Institute and the Fields Museum are in, as well as whatever other museums we have time for. I’m also glad to have restaurant recommendations. Everest looks perfect, and I suppose we need to eat some pizza too.
My wife is an elementary school teacher, and I know that they’ve been able to do tours of the Lyric Opera building, including backstage, on field trips. I don’t know if those tours are generally available to the public, but, if so, she’s said that it’s a very cool tour.
You’ll get a lot of strong opinions on this one. 
Pizzeria Uno is the originator of Chicago-style deep-dish pizza. They have two fundamentally identical restaurants (Pizzeria Uno and Pizzeria Due) a block apart in the River North area. Lou Malnati’s, Giordano’s, and Gino’s East, among others, all have their adherents, as well.
If you like art, be sure to check out the Museum of Contemporary Art as well as the Art Institute. The MCA always has some interesting stuff.
Get a beef while you’re there. You’ll see some dive-looking restaurants advertising “beef” or maybe “beef and dogs”. Stop in and buy one. But make sure to get lots of napkins.
You might enjoy an architecture tour. Too bad you’re not coming during the warmer months, because the boat tours are not to be missed – but there are walking tours year round. Even if you’re not really into that sort of thing, it can be fascinating. Chicago has a very rich architectural history.
Take in a show at Second City and there’s a good chance you’ll see a future SNL cast member or two. If you enjoy bending an elbow at some good neigborhood joints, head to Lincoln Park or Lakeview (and other 'hoods as well, I’m sure, but I know those).
And it may be touristy, and it’s more homogenous than it used to be, but there’s still nothing like walking up and down Michigan Avenue just to get a feel for the city and people-watch. Be sure to go down the stairs across the street from the Tribune Tower and grab a cheezbourgie at the Billy Goat. When you get to Lake St., head a few blocks west to State, and you’ll spot the el tracks you’ve seen on countless movies and TV shows, as well as the famous Chicago Theater. I’ve lived in the area my whole life, but I still love walking around downtown just for the sake of it.
It won’t be that cold. The Chicago Architecture Foundation’s boat tour is not to be missed.
ETA: Haha, I hadn’t even read Wheelz post before I posted the above. To add something new, be sure to include the neighborhoods in your travels instead of just the Loop/Mag Mile/Gold Coast. Hyde Park, Logan Square have plenty to do. Here’s a great essay on the much-overlooked neighborhood of Avondale.
Does the Lava Lamp factory still exist in Chicago and do they give tours?
I think that would be real fun.
Is Ed Debevic’s still around?
Drive through lower Wacker Drive, it is fun and scary.
:eek: Looks it.
Thanks for the links, guys!
They’re in Elmhurst; no idea if they give tours (most factories don’t, anymore, for liability reasons).
Yup, corner of Wells and Ontario. Though, I think it’s incongruous that they have the look of a '50s diner, but now play '80s music. 
I had to pay $15 to go to the top of the Hancock back in Dec. 
I had a class that ran past 5 the week I was there, and I was only there M-F, so I missed going to all the museums and stuff. All of them seemed to close at 5 or earlier during the week. I walked down to the Lincoln Park Zoo hoping to see the lights but they were closed, too. About the only things to do (besides eating & drinking - and I was alone so I didn’t do much of that, either) was walk up & down Michigan Ave. to look at the lights and go to the top of the Hancock. I really need to go back.
Not the Observatory. Go to the Signature Lounge instead. There’s a restaurant as well, but that’ll set you back more money than a drink at the bar. Mind you, if you get a pricey cocktail or two (instead of a beer or soda) that’ll cost you at least $15, but hey, better spending it on a drink than on a trip up a few more floors from there, IMO.
Last time I went, a turkey wrap and a soda at the Signature Room Lounge cost about the same as a trip to the top of the Sears Tower. So consider it a free lunch with your sight-seeing.
Oh, and everyone visits the Signature Room Lounge to look out at the city and eat appetizers so don’t feel like you’re going to be glared at by the staff or anything. I personally try to dress up at least a little to make an event of it but I always see people there dressed in standard tourist shorts 'n t-shirts.
The Signature Lounge is definitely worth a trip, especially in the evening, when the city is all lit up. Great place to grab a drink and have some conversation.
That said, I really do think the Sears/Willis Tower is worth a trip, too, especially since they installed those glass platforms. I went there a couple months ago for the first time since the new addition, and thought it was totally worth the price of admission for the experience. When I went (a Tuesday afternoon) there was absolutely no wait.
See the Chicago skyline from outside the Adler Planetarium.