The best August 2026 events in Chicago

The Chicago Boat Company and Chicago Canine Rescue are bringing back their second annual All Paws on Deck event at Rockwell on the River. Head to the Avondale spot to board a Duffy Boat alongside adoptable dogs and enjoy gelato from Dolce Arte (there will also be pup cups, of course). 

Nearly 10,000 competitors will swim, bike and run along the lakefront during Supertri Chicago (formerly called the Chicago Triathlon), which starts at Montrose Harbor before zooming down Lake Shore Drive and finishing on Columbus Drive. There are different courses for athletes of all levels, including a sprint and separate races for kids 14 and under. 

Jeppson’s Malört is attempting to set the world record for the most people to take a shot of this polarizing drink at once at its “Bad Decisions for Good Cause” event at Recess (838 W. Kinzie St.) on Sunday, August 30. The event kicks off at 5pm before the official attempt at 7:30pm. Malört will match $10 from every ticket sold to support Ravenswood Community Services, a nonprofit dedicated to providing food, housing and other supportive services to Chicagoans facing hunger and homelessness.

A Gen Z version of Grease takes the stage at the Apollo Theater this season. Vape! The Grease Parody is an Off-Broadway spoof of the iconic 1978 musical, complete with playful takes on the original storylines, modern references and, yes, vapes instead of cigarettes.

Gallagher Way hosts a free night market on most Thursdays through September in partnership with Common Goods, featuring dozens of local vintage vendors selling a mix of home goods, clothing, jewelry and more. Grab a glass of wine, browse the market and stick around to catch live music from a host of different artists.

Hailing from Texas, Grammy Award-winning singer-songwriter Kacey Musgraves made a name for herself with twangy tunes about small-town living, romance and staying true to yourself. She’ll stop at the United Center in support of her latest chart-topping album, Middle of Nowhere, and be joined by opener country band Midland.

Spin classes and weight lifting can wait for the winter. This summer, jump-start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn and in Wrigley Square on Saturdays from May through August.

Local no-kill animal shelter PAWS hosts its 26th annual 5K race at Montrose Harbor, where humans and dogs can make their way through a lakefront course while raising money to support the organization's work. Once you cross the finish line, you'll be able to enjoy live entertainment for humans and pups alike, including a dog agility course and a "doggy oasis" outfitted with pools for cooling off. Don't have a four-legged friend to bring along? Not to worry—there will be plenty of adoptable doggos for you to pet.

The producers behind South Loop Farmers Market are bringing a new shopping experience to the Water Tower Place. On Thursdays from July 9 through September 24, head to the fourth floor to shop vintage treasures, artisan goods and farmers market finds, and enjoy live music and local food. 

This annual fest and conference celebrating the iconic dance music genre born in Chicago brings a full day of DJ sets to Millennium Park. Acts this year are to-be-announced. The live music will be preceded by an open house and panel discussions, and the festival will wrap up with a chill-down session along the Riverwalk. For a full list of programming, visit the DCASE Chicago House Music Festival and Conference website.