The Field Museum! But that might be too much museums.

The Field Museum is definitely cool, if you have the energy for two museums in one go. Parking is insanely expensive in that area (starting at about $18 and going up). Where are you coming from? Are you visiting from out of town/state and staying in a hotel? Are you driving in from the suburbs? I can recommend places maybe to park and then take public transit in.

We're driving down from Milwaukee, but we're trying to decide between driving there and driving to Kenosha and taking the train in.

Have you been to the Art Museum before? To see everything may take longer than you might expect. Both times I was there I wasn't the one setting the itinerary and was only there for a few hours each time, which wasn't enough.

(It's also known as the Art Institute.)

There's no cheap parking downtown, but if you're willing to take the El, you could park further out from downtown and take the train in. Or take Metra, that'll work.

Fun things -- well, if you don't mind the cold, it's certainly worth walking over to Millennium Park to check out The Bean; it's about two blocks to the north. There's also an ice rink right there -- free to skate, although skate rental is $7. The Chicago Cultural Center is across the street, and has a neat "Stitching Salon" thing going this winter that might appeal to your wife.

The Architecture Foundation is right across the street from the Art Institute; again depending on your cold tolerance, they've got some pretty cool tours, some of which involve walking, others are in a bus I believe.

And yes, there's the Field Museum, as well as the Shedd Aquarium and the Adler Planetarium. They're a quick cab ride south of the Art Institute.

Beyond that, it's mostly shopping and office buildings in the Loop.

Whenever I visit the art institute, I very often hop over to My Thai for dinner. They're @ 30 S. Michigan Ave. Here is a short little blurb about it. Mmmm.

I think you can get four hours of parking at the Milennium park Monroe Street garage for $12. At least that's what I remember from the last time I drove, which was a couple of years ago. If you drive into the city on 90/94, exit Monroe East, drive through the intersection of Monroe and Michigan. The garage is underground, almost immediately on your left.

If you decide to take Metra from Kenosha, you'll be taking the line that passes by my house. Be sure to wave.

I always, always recommend having a drink (or nine) at the top of the Hancock. It's just such a beautiful view and the Cherry Blossom is easily the best frou-frou drink in the city.

The Art Institute is four visits, at minimum. Pick a few favorite genres and take your time with those. I do not recommend adding another museum, although both the Shedd and the Adler can be "experienced" briefly. Perhaps a small one like the Museum of Contemporary Art, but that's up across the river and ... it's cold.

I would pick the Art Institute, Millennium Park (and maybe other parts of Grant Park), the Chicago Cultural Center, maybe ride the "L" around the Loop if that's sufficiently novel.

State Street hasn't been a great window-shopping experience for years, alas, but if you're up to it you could hike up Michigan Avenue and toss in the Hancock observation deck (which as I always tell people, has more interesting views of Chicago than the Sears).

The Loop does have some decent restaurants, catering primarily to an office crowd, though. The southeast corner of the Loop is now moderately student-oriented. The north Loop is Chicago's microscopic "theatre district" and has some appropriate amenities.

You can cross the river into the North Pier/Navy Pier area, depending on stamina and weather. If you just want out of the cold, there's the underground shopping mall of Illinois Center (north of Millennium Park, under all those buildings; just ask, or watch for places where the most people are going).

If you ride Metra in, up top has the best views but the seats aren't as comfortable. You can get a $1 CTA bus ride from Ogilvie terminal.

It's hard to know what you want to do, there's plenty depending on your interest.

The Cultural Center is right nearby and boasts a beautiful Tiffany Dome. It's also free, has concerts and exhibits. Marshall Fields on State at Randolph also boasts a Tiffany dome. One of them is the largest TIffany dome, but I can never remember which.

Unless you're actually going to the MCA, in which case, you're in a different neighborhood. Not far away, but not right nearby anymore. In that neighborhood, you're very near to Cru, which is a nice winebar.

Yes a drink at the Hancock is an awesome thing because the service is awful, but the view is amazing. The martinis at Encore (just west of the Cultural Center) are better though.

There is a surprisingly good and fairly inexpensive sushi counter, just south of the Art Institute, at Jackson or Van Buren. Russian Tea Time is near Art Institute as well.

I recommend going into the Daley Center (it's a public building; you'll have to go through the metal detector) because it also has stunning views. Also, you can see the really cool "Atlas Shrugged" transformer on Dearborn and the Picasso, if you do. The Methodist Church in the loop also does tours (it's in the same building as Clarence Darrow's law office).

is there reasonably priced parking?

lol no. i would ride the train from kenosha (or bus, as dhartung suggests) and then walk and/or maybe snag a cab ride to wherever you guys decide to go, eg ROCK N ROLL MCDONALDS

have fun!

Hehe! That McDonald's is fascinatingly large.

Russian Tea Time is a little expensive, but it's a neat experience.