The best August 2026 events in Chicago

Sportsman's Club's Sunday BBQ series is back for another glorious year, bringing local restaurants to the bar's patio to cook a meal that's usually paired with a beverage. For the uninitiated, the takeovers are first-come, first-served, with the featured chef holding court over the bar's grill and menu. This year's lineup includes Bar Bambi, Pizz'amici, Milli by Metric, Kimski, Mister Tiger, Diego and more.

For one weekend each year, Southport Corridor becomes a mecca for taco lovers during the Lakeview Taco Fest. More than 10 restaurants offer their take on the tortilla-wrapped dish, serving delicious fare all weekend. You'll also be able to see Mexican wrestling shows, performances from local bands and kid-friendly activities, plus you can vote in a contest to crown Chicago's best taco.

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). 

For one blissful weekend, Fulton Street transforms into an open-air gallery and music venue for the West Loop Art Fest. Shop more than four blocks of art for purchase at this family-friendly festival in Fulton Market, where you'll also enjoy live music and plenty of solid dining options nearby.

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.

Revolve and Cotton are bringing their joint collection to Fulton Market for a four-day pop-up shopping experience. At The Cotton Shop by Revolve, you can browse the pieces, plus participate in a denim recycling program, get custom denim embroidery, snack on free goodies from Lil Sweet Treat, and snap pics in a photo booth. Five people each day will be randomly selected to receive a $100 gift card, and the first 50 guests will get a bag filled with beauty products to bring home.

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.

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.