SWMBO and i are going to Chicago for 2-3 nights at the end of June. She's never been and i've never spent much time there myself.
So... what do we NEED to see/do?
We like food, we like seeing things, she's big into photography, so if we could get an afternoon in one day of something cool to take pictures of, bonus.
Doesn't have to be automotive related, but if there's a super cool something there on that subject, we're open to it.
Lay it on me!
Would help to know more about what you are into and where in Chicago you're going to be. When I lived there some folks I knew just moved from Kansas and described Chicago as "an amusement park for adults." So there is something for everyone.
For example, if you like art or even tolerate it, the Art Institute of Chicago has probably the finest collection of impressionist artwork in the U.S. and one of the best in the world.
Shopping on the Magnificent Mile-- something your wife might be into more than you, of course.
Top of the tall building http://www.360chicago.com/. Great for the photographer.
The other Museums (Science seems more kid geared, but the Natural History Museum is awesome) and the Aquarium are all along the lakefront and easy to get to.
Car stuff? There's the Volo Auto Museum, though it is a bit out of town. Road America is within driving distance, as well, but maybe further than you want to go. You might check their schedule to see what's going on.
Of course, ya gotta eat the pizza. I like Giordano's. A bit touristy, but the pies are fantastic. Others will tell you Pizzeria Uno (the original-- not to be confused with the failed franchises) or Pizzeria Due. Man, I'm making myself hungry.
Do you like architecture? Take a Chicago River architecture tour: http://www.chicagoline.com/schedule.php. I really enjoyed this, a nice few hours floating down the river learning about all the buildings. I believe you can also purchase overpriced alcohol on board.
What kind of museum do you like? Any of them are good, but my personal favorite is the Museum of Science and Industry. Also available are the Art Institute (awesome, but I've been there too many times), Field Museum, Shedd Aquarium, and Adler Planetarium. The last three are right next to each other.
What kind of food do you like? BBQ? Steak? Polish? Italian? Greek? Jewish? You name it, there is a good one there, and I know of a few good ones personally.
What about music? Old Town School of Folk Music is always a cool place to visit. Numerous blues and jazz places as well.
Second City comedy club is always a good bet. Your sides will probably be hurting by the end of it.
Two zoo's, haven't been to either one since I was 10, but both are good. I guess... Lincoln Park Zoo and Brookfield Zoo.
Chicago Shakespeare theater is on Navy Pier, always can catch a good show there.
Also, this article is about 150% spot on: http://go-go-go.org/2013/02/04/how-to-visit-chicago-like-a-chicagoan/
There is no shortage of things to do / places to eat in Chicago--- that's for sure.
The Museums are great-- and all along the waterfront. If the weather is nice, walk through Grant Park (lots of good photo opportunities) The Science and Industry Museum (with German WWII U-boat out back), Art Museum, and Field Museum are all excellent.
If you are looking for Chicago deep dish pizza-- Lou Malnatis' or Gino's East are both good. If you don't want the gut-bomb, awesome thin-crust pizza is everywhere too--- and it's not that cardboard crap they sell in NY. 
Catch a game at Wrigley Field if you can. Even if you aren't a baseball fan-- it's worth the experience.
Fantastic live music abounds in Chicago-- pick up a "Reader" local free paper to see who's playing where. There is bound to be someone good playing locally. If not, Kingston Mines is a safe bet for good music ( although the crowd may be a bit "yuppy-trendy-hipster") It's just down the street from Wrigley in "Wrigleyville"
Tons to do and see--- and it's a very friendly big city. You should have a blast.
I'll address the rest of the questions later when i have more time, but we berkeleying LOVE aquariums. 
Portillos.
I was just in Chi town for the first time for business week before last. We stayed downtown on Michigan ave.
Highlights of my trip were:
live blues at Blue Chicago. Awesome, especially early in the week when it's a little less tourist-packed. Great little bar, outstanding music.
Billy Goat's Tavern - You can reference Belushi's CheeseBorger CheeseBorger sketches, or the Cubs Curse, but I care about neither. It's just a freaking awesome dive bar. Old, unimproved, perfect. Downstairs subway level off Michigan Avenue.
We had a big reception thing at the Shedd Aquarium. It was okay....but seemed a bit past its prime. The Jellyfish exhibit is mesmerizing though. The freshwater tanks upstaris that simulate different river ecosystems from around the world looked cool but I didn't have time to really check them out.
Best meal I had was at Coco Pazzo - authentic countryside Italian. Not cheap but not the most expensive place we ate either. The antipasti appetizer was really good, as was the braised rabbit. They have two locations, we ate at the cafe one which is a little cheaper and less formal but serves nearly the same menu.
mtn wrote: Portillos.
A must-stop when in Chicago, as is Gino's East and the Chop House.
I like to grab a drink at bar at the Signature Room because you get the 95th Floor view without paying for the Sears Tower or a fancy meal.
If you are feeling romantic, I recommend Geja's Cafe. It is a little Fondue place, make a reservation and ask for a private table. The booths have little curtains and everything. The SO will love you for it.
The only thing that I have done in Chicago that wasn't eating, drinking or shopping was The Blue Man Group. Best place to see them of all IMHO because it is small and the entire place is setup for their show. Way fun.
Pizza, lots of it
Go see Sue at the Field Museum, brought out my inner Dinosaur nerd.
Don't look across from the Field Museum to the Navy Pier, and think, "I can walk there." You can't, and I'll leave it at that.
bigdaddylee82 wrote: Don't look across from the Field Museum to the Navy Pier, and think, "I can walk there." You can't, and I'll leave it at that.
Sure you can. It's only... what, 2 miles maybe?
But yeah, that is longer than you want to walk while on a trip.
In reply to mtn:
Technically, I'm sure it is physically possible, though it is much farther away by land, than it looks when viewed across the lake. We wound up in an area of what I assume are high-rise apartments, at the top of a very tall retaining wall, looking down at several lanes of a very busy road we still had to cross, and still 1/2 a mile or more to go. We took a cab from there, the cabbie just laughed at us, but applauded our effort.
bigdaddylee82 wrote: In reply to mtn: Technically, I'm sure it is physically possible, though it is much farther away by land, than it looks when viewed across the lake. We wound up in an area of what I assume are high-rise apartments, at the top of a very tall retaining wall, looking down at several lanes of a very busy road we still had to cross, and still 1/2 a mile or more to go. We took a cab from there, the cabbie just laughed at us, but applauded our effort.
Bah, you did it wrong! There is a walking path right along the lake that you can take straight from the Field Museum to Navy Pier.
Still a long way though.
Great advise has been given.
I will second the idea of a Cubs game. It should be done! I am not a big baseball fan but take pride in saying I have been to an afternoon game a Wrigley.
If staying downtown, take the train to Wrigley.
My wife and I rented a tandem bike on rode the downtown waterfront. For me it was fun but she references it all the time. She really enjoyed it. It was a perfect weather day. A little touristy but not overly expensive and fun.
For hotels, I have had luck with Priceline in years past. On the weekends, Chicago hotels are either packed (some convention or event) or rather empty.
I have gotten as good as $69 per night for The Hyatt on Wacker via Priceline. It is an 1,800 room hotel so unless they have it fully booked with their meeting space then it is rather empty, and cheap.
Just expect that the downtown hotel will jam you on parking at $25 per day or more.
Oh--- and if you find yourself near Logan Square---- visit Marble Bar+ Grill. Ask for Jay, and tell him I sent you. He's an old buddy of mine, and he'll hook you up!
http://www.marblelogansquare.com/
you may want to take a cab home though....
I'll also be in Chicagoland (Autobahn Country Club) at the end of June--- competing in a 4-hour karting race to help end homelessness in Dupage County IL. (where my hometown is)
http://dupagepads.org/race_to_end_homelessness/
I'll be on the PB+J's team sponsored by the Davi Law Group. (shameless plug) Feel free to donate to a good cause, or come out to root us on!
https://dupagepads.ejoinme.org/MyEvents/Drivefor75/PersonalFundraiserSignupFundraising/tabid/534439/Default.aspx?joinme=34181
http://www.chicagobrewbus.com/
We just went on this last month, and it was actually pretty fun. Lake Effect and Haymarket make some great beer(Disclaimer: This is of course if you've gotten past your addiction to that Rolling Rock crap)
Otherwise, Giadornos(sp?) pizza, and a few other things.
ProTip: SKIP PUBLIC TRANSIT!!!! Whore up UBER to get around Chicago. It worked well for us
pinchvalve wrote: The Blue Man Group. Best place to see them of all IMHO because it is small and the entire place is setup for their show. Way fun.
Just like Astor Place Theatre in Manhattan. 
I'm a big fan of the museum of science and industry. Not too many places where you can go to walk through a WWII U-boat. (It's been a few years, but I assume it's still there)
In reply to wae:
It's still there, it's just underground now. 
Honestly, there are so many great places to eat in Chicago. My inlaws live in the South Loop, so there are a lot of places to eat.
If you're interested in the most delicious foot long grilled cheese, you need to stop in at The Scout Waterhouse. They add bacon or ham or egg and it comes with a tomato bisque to dip it in. http://instagram.com/p/ekxKIllJtI/
I also second the Museum of Science and Industry. Not only do they have the U-505 German U-Boat, they have a Boeing 727 along with several other planes, the Spirit of America land speed car, the Pioneer Zephyr train, a real awesome model railroad, and the Coal Mine which has been an exhibit there since I believe the 1930s.
The Shedd Aquarium is pretty good. The reef exhibit is worth it alone. The Field Museum is pretty awesome too. I also enjoy the Chicago History Museum where there are many artifacts from the Chicago Fire.
Navy Pier is a tourist trap and rather expensive, but it's still popular.
As someone already said, there is a lot to do.
You have gotten a lot of great suggestions, I'll add a couple, any museum is a plus, Beggars Pizza is the best, skip the Cubs( they stink and yes I'm a White Sox fan :D). If you go to a cubs game, walk a block northwest to Yahtzees bar for a buffalo chicken pizza, awesome. Goose island has very good craft beers. No matter what anyone advises, just enjoy our fine city. One last thing, if you are driving, be prepared to pay an arm, leg, and first born for parking :D Thanks Mayor Daley!
Try the palace grill
I didn't read all the posts but it looks like the architectural boat tour, aquarium (really nice when we were there 7-8 yrs ago) & pizza were mentioned. Did anybody bring up hot dogs? Chicago dogs are different & in a good way. Sears tower (or whatever it's now called) observation deck is kinda cool in an overpriced touristy way if you've not been in big buildings. After 10 minutes we'd had enough. Also, a bunch of Frank Lloyd Wright stuff in & around the area if that's interesting.
Edit to add: the river otters were frisky the day we went to the aquarium. SWMBO & I used to joke that it was always when her roommate was with us, but this & the giant tortoises at the Columbia zoo changed my mind. Tortoises grunt really loudly when doing it...
This thread helped me remember how awesome Chicago is. Lots of great suggestions so far.
In reply to secretariata:
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