The Second City

If you're a fan of improv comedy, or just comedy in general, you can't visit Chicago without planning a visit to Second City. Tons of the greatest performers from Saturday Night Live honed their hilarity here, and when you catch a show, you can see why they went on to do big things.

It doesn't matter when you're going to be in town, because Second City always has something funny on the calendar, though you'll have a lot more options when it comes to the schedule if you visit on the weekends.

Here's a tip: if you book your tickets through their website, you can actually snag a deal for a cheap meal at one of the nearby restaurants too.

This place is definitely worth it if you like comedy at all. Just make sure you book your tickets ASAP because they sell out! Last time I went it was a Wednesday night and there weren't any tickets available for the mainstage show when we checked at the beginning of the week. Fortunately, there are more options than just the mainstage shows. We saw a show in a different theater in the same building that was still pretty funny. They also have a walking tour of the neighborhood during the warmer months!