1. Check out the American classics
Spend the day at the Art Institute to see “America After the Fall: Painting in the 1930s.” This iconic collection of pieces by Edward Hopper, Georgia O’Keeffe and Grant Wood explores the Great Depression's impact on the American identity. (Art Institute of Chicago, 111 S Michigan Ave, 10:30am-5pm. Price included in museum admission)
2. Sip some cocktails and groove to jazz
The Whistler hosts Chicago’s finest jazz artists and combos three nights a week for a set of free live music. Enjoy the Whistler’s incredible cocktails and settle in for a nice, relaxing evening. (The Whistler, 2421 N Milwaukee, 9:30pm. Free)
3. Laugh at Chicago’s best improv
iO doesn’t tout itself as the home of longform improvisational comedy for nothing. Check out the Armando Diaz Experience to see what all the hype is about. (iO Chicago, 1501 N Kingsbury St, 8pm. $12)