Ah, the crown jewel of comedy in Chicago, and well deserved, at that. Second City launched the careers of hundreds of famous side-splitters. If you’re going to hit one comedy show in Chicago, make it this one. There’s a reason there’s a comedy school here, and that comedy scouts are frequent visitors. It's just that good.
A word of warning: The website is confusing. You’re going to see a whole bunch of shows to choose from and multiple theaters. The resident theaters are the Mainstage and E.T.C. (which stands for nothing, from what I can surmise). The Main Stage is the larger venue, with more broad-based improv, where you’ll see a revue or a “best of” style show, versus the more intimate E.T.C., which hosts more topical and satirical shows, like, say, A Clown Car Named Desire. At both venues, expect to share tables and rub elbows with your neighbors; seating is quite tight. UP Comedy Club, located on the third floor of the complex, is a third option. Operating in a more traditional comedy club manner, it brings in a rotation of stand-up and improv. If you can’t score a ticket to any of the above, you’re still in luck. Every night except Friday, Second City puts on a free improv show following its last performance. (It usually starts around 10:30pm, but check the schedule to see when the last show runs, and plan on the freebie starting 2 1/2 hours later). Note: Kids 10 and up are allowed at Second City, but keep in mind it’s a nightclub atmosphere, and the language and topics aren’t exactly kid-friendly.