We did 3 days in Chicago in February and
Obner gave me a lot of good advice. We also have 4 kids, and here is what I discovered. I meant to post a response to that thread afterward, but might as well do it here.
We spent almost an entire day at the Field museum, and everyone had a great time. They seem to have a lot of temporary exhibitions, which cost extra. None of them really caught our interest so we only did the permanent exhibits, and even then still didn't see it all. Our feet were aching by the end, but the oldest didn't want to leave.
After the Field, we went to the Adler planetarium, just a short walk away, and caught a couple super planetarium shows. My kids all like science, and we were all ready for some sit-down time by then. We were able to see the museum parts in between shows. I found out later that our Planetarium membership would have gotten us into a lot of other sites at discount... not sure if this is the "city pass" other people mention, but it seems like a good way to save some cash on admissions. Plus the membership benefits are good in other cities - we just saved $40 in Milwaukee because of that Adler membership.
I was pleasantly surprised how much they all liked the Art institute - I'd expected to be dragged out by a bored family after an hour. Instead we spent 3-4 hours there, so much that we missed out on the museum of science & industry planned for that afternoon (next trip!)
The Bean in Millennium park is probably the single site we most talk about - it seems to have stuck in my kids' memory. Of course, it was 8 am and 20 degrees out when we were there, so we basically had the thing to ourselves.
We were very disappointed with the children's museum. The youngest liked it, but the rest of us were ready to leave after a half-hour. Our hometown has a great children's museum, at which my 11 year old daughter volunteers and helps plan events. She in particular expected more from a big city museum.
We missed out on the Shed Aquarium: it was a free day and the line was insane. Easily a 2 hour wait. Since we were planning on hitting Seaworld in Florida the next week, it didn't seem worth it. I'd still like to go there on the next trip.
We went to the Lego place (a typical lego store - if you've been to one, you know what to expect) and also the American Girl place (both girls blew most of their souvenir money here) but otherwise didn't do much shopping. We went up the Hancock at night (almost empty of other tourists) and ate dessert at the Cheesecake factory, located on ground floor.
We stayed downtown, less than a block from a Red line station. I'd assumed that all Chicago transit lines were elevated, but the red line stations are below ground, like London or Manhattan. Made a big difference in February with little kids. Staying downtown may have cost more, but as I'm sure you're aware being close is a huge benefit with little legs and excess baggage.
By dinner time we were usually pretty beat, but had no problem finding great kid-friendly places to eat. One night we had Lou Malnati pizza delivered to the hotel room. (if you do, pack paper plates and plastic forks.) Fantastic - I'm craving it now.
I hope you have a great time, and I look forward to hearing about your trip - The next time we go it will be in the summer, so the zoo and some architectural walking tours are planned. The wife and I look forward to an adult only trip someday too.
