1. Watch a musical under the skyline
Tonight on the Millennium Park Film Series slate: Grease. Bring a picnic and some friends to watch the kids of Rydell High sing their hearts out. (Millennium Park, 55 N Michigan Ave, 6:30pm. Free)
The Olympics are about so much more than just sports. Learn the full story of the 1936 Berlin Olympics, which Hitler used as a vehicle for his racial supremacist ideas. (Illinois Holocaust Museum and Education Center, 9603 Woods Dr in Skokie, 10am–5pm. $12, seniors, students $8, children $6)
3. Sip cocktails and watch live jazz
Head to the Whistler as Chicago’s best jazz artists take the stage for a free set. You’re definitely going to want to have a cocktail (or three) while you’re there. (The Whistler, 2421 N Milwaukee Ave, 9:30pm. Free)