Me and the Missus were kicking around the idea of a quick 2 or 3 day trip to Chicago just before the 4th. We've never been to Chicago, other than flying into and out of O'Hare. Here's my questions......
1) The cornerstone of our trip is to catch a couple of the Reds games while they are at Wrigley. I know the Cubs' fan reputation, but will we really have any problems while there wearing our Reds apparel ?
I've never had any problems wearing Reds cap and t-shirt. However, I would avoid the bleachers.
2) Other than Navy Pier and the Sears (used to be) Tower, what else falls into the "While you're in town, do not miss ____________________" category ?
Navy Pier is very "touristy". Others have said this already, but Millenium Park is a must. Since you'll be in town just prior to the 4th, get to Grant Park for the Taste of Chicago. It will be crowded, but it's still a great place to walk around, get a few small samples of local food, and people watch. Walk off the calories along the lakefront. If you like popcorn, get over to Garretts. Architectural tours along the river are great. Lincoln Park zoo is not as nice as Brookfield, but admission is free and is right off the lake if you want to head out to the beach for a bit. View from Hancock building is better than Willis Tower, but I haven't had a chance to go out on the new glass skydeck yet, which seems pretty cool.
3) Hotel recommendations ? Near Wrigley if possible.
Can't help you with near Wrigley, but Hyatt on Wacker and Intercontinental on Michigan Ave are both nice.