The best August 2025 events in Chicago

The Shedd Aquarium's weekly summer concert series presents a rotating lineup of jazz bands on its scenic lakeside terrace, where attendees can dance, have a drink and get a great view of the Navy Pier fireworks. Guests also get access to the Shedd's exhibitions, meaning that you can gaze at the creatures that inhabit the Caribbean Reef, snap a picture of a cute sea otter or touch a sea star.

This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

Wrigley Field-adjacent plaza Gallagher Way is once again showing free outdoor movie screenings this summer. Admission is free and attendees are welcome to bring their own food, enjoy on-site concessions or snag a meal from nearby restaurants like Big Star and Smoke Daddy. VIP seating is also available—check out the Gallagher Way website for more details. Gates open at 6pm for each screening and the movies start at 7:30pm. May 21: Hook June 4: Twisters June 11: The Parent Trap June 25: Inside Out 2 July 9: Wicked July 16: Top Gun: Maverick July 30: The Little Mermaid August 13: Moana 2 August 27: Crazy Rich Asians September 10: Space Jam September 17: Remember the Titans

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 8:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

During the summer, one of the best aerial displays you'll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

Don't be surprised if you get a neck ache from looking up during this beloved two-day event, which brings an array of flying acts to the Chicago lakefront. Join throngs of people at North Beach and surrounding areas (you're best off sticking along the lakefront from Fullerton to Oak Street) to catch air and watercraft demonstrations, including the U.S. Air Force Thunderbirds and the U.S. Army Parachute Team Golden Knights. Civilian acts round out the show with aerobatic daredevils like Bill Stein Airshow, Kevin Coleman and the Warbird Thunder crew, plus stunt biplanes, mini jets and vintage aircraft performing choreographed chaos over the lakefront. 

A spot on the pine bleachers at Drip Collective has become one of the most coveted seats in the city, thanks to the cafe's adventurous beverage menu (hello, mango sticky rice matcha latte!) and hyper-local event programming. Aside from piping hot coffee, Drip has been bringing a different kind of heat this summer with Hot Drip Sessions, a weekends-only DJ pop-up. August marks Hot Drip Sessions' last installment of the summer, featuring house, cumbia and afrobeat sets from locals like Aced Spade, ADONIA and more. Can't make it to West Loop? Drip Collective has been uploading past Hot Drip Sessions onto their YouTube channel. Dive into the archive here.   

Take a car-free ride along DuSable Lake Shore Drive during this annual biking event, which closes down the lakeside thoroughfare to vehicle traffic and allows cyclists to ride through a 30-mile route dotted with rest stops, water and snacks. You'll have to wake up early (the course opens at 6:30am) and enter through one of designated entry points along the road—but the novelty of biking on a stretch of pavement that is decidedly not bike-friendly is worth the hassle. Plus, proceeds from the event support the Active Transportation Alliance, a nonprofit organization that working to improve conditions for pedestrians and cyclists throughout Chicago.

Sportsman's Club's backyard 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. Food is priced a la carte. Check out the full lineup below and start planning your Sunday afternoons accordingly. Starts at 4pm. May 18 - KasamaMay 25 - Rootstock June 1 - Pizz'amiciJune 8 - Mi Tocaya AntojeriaJune 15 - Bacchanal (New Orleans)June 22 - Gibsons ItaliaJune 29 - PerillaJuly 6 - ObelixJuly 13 - AvecJuly 20 - MirraJuly 27 - Brasero & El CheAugust 3 - HawkmoorAugust 10 - ProxiAugust 17 - Joe Flamm & Day Off GroupAugust 24 - Shaws Crab HouseAugust 31 - Lula CafeSeptember 7 - Tripping Billy Z

Brush up on or test out your language skills at this casual hangout at Revolution Brewing. There will be tables set up for each requested language, so attendees can make some new friends while practicing speaking a language they’re learning or already know. All levels are welcome.