re: Planning a trip to Chicago in September. Tips?

We had a great time in July. Stayed at Sofitel, which allowed us to walk a lot. I seem to remember a lot of solid deals on hotels (and this was July 4 weekend), and we were looking at 4 and up I think. I'm sure you'll find something affordable downtown, there are a ton of options.

If you're an adult, take the architectural tour, perhaps the morning after you arrive. Gives you insight to other stuff you'll see, we really liked it. We went to the beach, drank at a lot of bars we passed, and packed in a good bit of touristy stuff. Did Willis, which was worth it. Went to a Cubs game and hung out in Wrigleyville, certainly recommend that. The parks were slammed with tourists so we largely just walked by, but I know people recommend checking them out. Went to the Art Institute, which I'd highly recommend if you're into it.

Food wise, we weren't there for long, but we did touristy pizza (Giordanos and Uno). Loved them both, even if locals don't favor them. Also went to Chicago Chop House and Gibsons, and would recommend the latter although Chop House is solid.