Love Chicago. Might have to drag the BF there this summer as I haven't been in over a year. Architecture tour is a MUST. It's a field trip I take my students on every year. Chicago line has free starbucks and cookies, LOL. I think I've done all of the companies at this point. I like staying close to/on Michigan Ave. I've stayed at the Sheraton on the river, and the W at Navy Pier. Also the Intercontinental on Mich Ave oh and the Waldorf. Others have mentioned the food. Obv, must get a deep dish Pizza. There are a few speakeasy's if you're into that. If you're into architecture try and do one of the FLW tours. I've done both the home/studio and the robie house. Hit up the Sears Tower, or the Hancock. I like the Cubes at the Sears, I think the Hancock has "the tilt". The art museum is nice. We used to show Ferris Buellers Day Off on the bus on the way to Chicago. The year we did the art museum, we found all the kids at the reenacting the scene starring at the painting, LOL. It's one of my fav cities! Shedd's can be good, the museums, etc. You really can't go wrong.