My wife, 2.5 year old son and I traveled to Chicago on vacation from 4/14-4/21/05 and stayed the seven days at the Homewood Suites. It was perfect for us. Like other suites we have stayed in (i.e. Residence Inn, Hawthorne Suites, etc.) the suite had a small kitchen, living room and bedroom. Our son stayed in the living room on the sofa-sleeper while my wife and I stayed in the room. It was very private and worked out great. The room had a good view of the river and the River North. The location was great, close to Michigan Ave and shopping as well as various restaurants, including Joe's Steak and Crab, Pizzeria Uno, ESPN Zone, etc. The Red line (i.e. subway or "L") was only about a block away. Moreover, the great thing about the hotel was that they provided breakfast 7 days a week and from M-Th dinner as well. The best thing about this aspect is that they provided take out boxes if you wanted to bring the food up to your room! That was very convenient something that I never received at either Hawthorne Suites or at the Residence Inn. What I would do is wake up and go down and bring up food for my wife and son while they continued to rest. Please note that although the staff was generally nice and attempted to be helpful, this is NOT the Four Seasons so don't expect it to be. For example, the staff does not make reservations at restaurants, but will give you the phone number. Again, for the price ($139/nt, a discount if you stay at least 7 nights), it wasn't that big a deal anyway. The telephone system worked out well, too. They do not charge if you are dialing a number in that particular area code (i.e. within the loop). If I visit Chicago again, I would definitely stay at and recommend the Homewood Suites.

Also, I would recommend taking the subway from O'Hare to the hotel. You would take the blue line (the entrance is right at the baggage area, if flying AA) transfer to the red line at, I believe, Washington, going North, and two stops later you get off and walk to the hotel a block. The only issue is that with a young child, it was a little bit of a walk going down stairs through a long tunnel and back up some stairs on the transfer, but for $1.75 a person (verses $35 for a taxi) you can't beat the price! Also the subway is fun for the kids. Just be careful about various individuals traveling the subway, like any other big city. Watch your bags, wallets, etc.

As for getting around the city, overall, I realize that Chicago is not that convenient a city to get around. It is actually fairly confusing. The subways don't really go near many of the museums. The bus seems a bit more convenient, but the system is a bit confusing. Taxi apparently is one big way to travel, but the cost can be an issue. We found walking to be fun and rather enjoyable, albeit tiring, but it was a nice way to get familiar with the city.

As for restaurants, I would recommend Joe's Steak and Crab. Very good food, nice service. Our waiter was Scott and he treated us well. We also ate at Morton's and I believe that Joe's was by far a better steak place and the price was a little better.

As for pizza's I personally liked Pizzeria Uno, it was very very convenient as for the location. Just be prepared to wait for a table or for pizza about an hour. My wife liked Lou Minati (sp?). We didn't particularly like Gino's East as much. The pizza was so so and the price was about $5 more.

As for museums, we got the city pass and actually went to all 6 destinations. The best museum for kids was the Museum of Industry and Science. To get there, we took the Metra which was $2.05. We would walk down Michigan Ave to the Metra station right across from the Cultural Center and got a ticket. Just remember the Metra is similar to Amtrak and that there are certain times that the train comes. It is NOT like the subway. So we had to wait about 45 minutes to get on one of the trains. It dropped you off about .5 miles from the Museum (I cannot recall the actual Avenue to take...59th?) and it was a nice short walk. The museum is great for kids who enjoy trains, airplanes, etc. My son loves trains and they have an incredible toy train system going as well as two other trains within the museum. You could spend a number of hours at the museum so plan accordingly.

Museums that I did not particularly like was the Adler Planetarium, rather boring. The Aquarium was nice for kids as well. I would say that it was probably comparable with the Monterey Bay Aquarium. The dolphin show is okay. Field Museum was okay. Probably better for older kids. I was surprised in seeing that their dinosaur exhibit was just okay. Sue was nice to see (the T-rex), but other than that, they didn't have much else in the way of dinosaurs. I did feel, however, that the Field was better than the Natural History Museum in New York. The actual exhibits seemed more up to date than that of the NHM in New York. The Art Institute really is not for kids. We went there and my son did well, but he got bored pretty quickly.
The Hancock Observatory is nice as well. The dates we went to these museums, there were no lines and we had a great time overall.

As for other things to see and do, I would recommend the Wrigley Field tour, neat inside look of the stadium. You get to check out the locker rooms, dugouts, field, press box, bleachers, etc. We also took the Wendela cruise line that takes you onto the lake and on the Chicago River and that was great. The cost for the 90 minute tour is the same as the 60 minute tour and it takes you onto Lake Michigan. I would recommend this. The cost was $19 a person. Another great place to take the time out for is the Lincoln Zoo. It's actually a very nice well kept zoo and it also is free! To be quite honest, I've been to the San Diego Zoo a number of times, and although the SD Zoo is much larger, I actually prefer the Lincoln Zoo. The size is not as huge, the atmosphere is actually nicer and it is pretty kid friendly. To get to Lincoln Park, however, is a bit difficult, so I would recommend the bus. the subway goes nowhere near this location. You could walk, but that is a pretty difficult trek from the River North.

One further thing to note when traveling with kids, child seats are apparently required. So if you plan on taxi or renting a car, keep this in mind. That's one of the reasons why we walked a lot and took the bus or subway.

Seven days is a good amount of time in Chicago. If we had another 2-3 days we would have had the chance to take a look at Oak Park (home of one of the Frank Lloyd Wright homes), some of the colleges (i.e. Northwestern and U of C), or taken a trip to either Wisconsin or Indiana. In fact, the Lincoln Museum apparently just opened up while we were there, but Springfield is probably a good 3-4 hours away by car.

Hope that helps.