I spent Labor Day weekend in Chicago with four girlfriends. It was my fourth trip, so I thought I'd list a few of the things we did in case other non-first-timers are looking for things to do!

Robie House: This is one of Frank Lloyd Wright's houses, in Hyde Park next to the University of Chicago. I was mildly interested in going at first, but am very glad we went; the tour was really fascinating to me. Definitely recommended if you're at all interested in history and/or architecture. The tour was $15 each. We took a cab down from the Loop to save time (about $23), but rode the #6 express bus back from the Museum of Science & Industry stop, about a 10-15 minute walk from Robie House. (Unfortunately we didn't have time to see the museum too! It's on the list for next time.)

http://gowright.org/research/wright-robie-house.html

Second City walking tour of Old Town: I think this is a fairly new offering from Second City (at least, new since my last trip). We really, really enjoyed it. It's a fun mix of Chicago and Old Town history with a lot of Second City history mixed in. Margaret, the tour guide, has been a docent with the architecture foundation (and I think other places as well), and is also an improvisor who's performed at Second City, Improv Olympic and other theaters, so she's perfect for this tour. If you're looking for an in-depth history tour, this probably isn't the best one, but if you're looking to learn a little about Old Town and laugh a lot in the process, it's excellent.

http://www.secondcity.com/performances/detail/633/

Food: We ate at Lou Malnati's, Kinzie Chop House (River North), Twisted Bakery (Old Town), and Davanti Enoteca on West Taylor. All are definitely recommended. Davanti is a cab ride from downtown - we thought about taking the el and walking, but were glad we didn't. Also, this was the first time I'd had Garrett's popcorn and I can't believe I hadn't done it before. Publican was on our list, but unfortunately they didn't have a Labor Day brunch, so we went to Publican Quality Meats instead. It was good - I wouldn't rave about what I had (the tuna melt), but definitely worth a stop if you're in the area.

We also went to a Cubs game, my first. The Cubs were up by two, then proceeded to lose the game in fairly spectacular fashion. I'm told this is a traditional Wrigley experience.

Nice report! The Second City tour sounds like fun. Thanks for sharing your experience. You've given me ideas for when I go to Chicago again.

Great report! I'm headed to Chicago next week and will definitely check out the Robie House. Glad you were able to try out Garretts!

Thanks! I'm glad it's helpful!

Sounds like a fun trip, jent103! Thanks for posting.

Glad you had a great trip. You only need to visit another thousand times to experience everything Chicago has to offer. Post when you come back and I will gladly help add to the Chicago experience.