We drove to Chicago last year, but the Sault crossing! We loved Chicago, a very clean, walkable city! We stayed at the Four Pointes by Sheraton, 1 block from the mag mile. Loved it! Great location. I think our fam's fav thing to do was the Cubs game, what a great atmosphere. I have a 10 and 11 year old girls, and it was their first time at the ball game, and they loved it! We also did Shedd Aquarium, and the architecture tour on the boat. There is a great free trolley that takes you to Navy Pier as well! We also did the tower. It was a great city, with great restaurants as well. We liked Weber Grill for dinner, we visited it twice. The pitcher of Sangria was expensive but awesome. It is an expensive city, more so then even Toronto. We also got our hotel at the 4 pointes on a travelzoo special, it seems to come up often, not just that hotel, but many Chicago hotels! If you would like anymore help just let me know. I was doing the same thing last year, asking for info, if you do a search on these boards you may see some of my posts about it!