1. Get jazzy
For a few nights each week, some of Chicago’s best jazz musicians take the stage at The Whistler for the Relax Attack Jazz Series. Spots fill up quick so show up early, grab a cocktail and claim your seat. (The Whistler, 2421 N Milwaukee Ave, 9:30pm. Free)
There are tons of open mics all across the city, but at iO, you’ll find a range of comedic acts and experience. Whether you’re a comedy veteran or stand-up newbie, all guests are bound to have a good time. (iO Theater, 1501 N Kingsbury St, 10pm. Free)
Wander through Aaron Siskind’s photography exhibit of everything from chipped peeling paint to landscape shots. Learn how one of the major influencers of the Abstract Expressionist movement viewed the world. (Art Institute, 111 S Michigan Ave, 10:30am. $14–$25)