The best Memorial Day weekend events in Chicago for 2026

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

This small-yet-comprehensive military library and museum is offering free admission on Saturday, May 23 in honor of Memorial Day. Visit to check out The War of 1812: Countering Peril on the High Seas and at Home, an exhibit chronicling the conflict between the U.S. and the U.K.

Want to know what's even better than a frozen cocktail on a hot day? A frozen cocktail on a rooftop on a hot day. Cool off all Memorial Day weekend long with drinks at these sky-high watering holes—just be prepared to make a reservation or brave a wait for walk-ins. 

Chicago's public beaches officially open for the season on Friday, May 22, at which point visitors are permitted to swim daily from 11am to 7pm. Slather yourself in sunscreen and keep an eye out for beaches with fun amenities like kayak rentals, concessions and picnic areas—and might we suggest dinner and drinks at a waterfront restaurant after your swim?

Not brave enough to take a dip in Lake Michigan yet? Get out on the water with one of the city's best boat tours, from mesmerizing architecture tours along the Chicago River to wind-whipping speedboat cruises on the lake. You can even rent a small electric boat and be your own captain for a day, if you're feeling adventurous.