With long days and warm nights, summer weekends are made for exploring. Whether you’re staying local or venturing out, here are a few events worth adding to your calendar.
Get Inspired at Glenwood Avenue Arts Fest
The Glenwood Avenue Arts Fest returns to Rogers Park with three days of live music, street food, and more than 100 artist booths lining the neighborhood’s cobblestone streets. The free grassroots fest offers open studios, live art demos, and a chance to chat directly with local creators. Grab a drink from a nearby bar, explore the murals under the train tracks, and enjoy music on outdoor stages late into the evening.
Date: August 15-17
Time: Fri 6PM-10PM; Sat 11AM-9PM; Sun 11AM-7PM
Cost: Free
Location: 6900 N Glenwood Ave
More Info: glenwoodave.org
Catch the Thrill at the Chicago Air and Water Show
Look up! The city’s iconic Air and Water Show soars back into town, with the U.S. Air Force Thunderbirds headlining the 2025 lineup. Settle in along the lakefront between Fullerton and Oak Street (North Avenue Beach is prime viewing) for aerial acrobatics, parachute jumps, and flyovers that rattle your bones. Herb Hunter returns as the longtime voice of the show, narrating stunts and skydives from the ground.
Date: August 16-17
Time: 10:30AM-3PM
Cost: Free
Location: Along the Lakefront
More Info: chicago.gov
Head to The Great American Lobster Fest
Navy Pier hosts this annual seafood bash, where lobster lovers can dig into a full East Coast-style feast featuring corn on the cob, buttered potatoes, and more. Expect live music, games, lakefront views, and non-seafood options too! Go big with a Lobster Meal ticket for reserved seating, DJ sets, and easier access to the goods.
Date: August 16-17
Time: 12PM-8PM
Cost: $65+
Location: Navy Pier, 600 E Grand Ave
More Info: greatamericanlobsterfest.com
Pedal with Purpose at Street Love Ride
Light up your bike and join hundreds of others for this annual West Side community ride focused on peace and positivity. The pre-ride party includes music and giveaways, outside St. Agatha Church, before the group pedals a nine-mile route at sunset. Glow sticks, balloon vests, and back-to-school supply donations are all welcome.
Date: August 16
Time: 8PM-10PM
Cost: Free with Registration
Location: St. Agatha Church, 3147 W Douglas Blvd
More Info: eventbrite.com
Experience Taste of Africa 2025: Afro-Fusion on the Beach
Africa meets the world at this high-energy lakeside celebration of food, fashion, and culture. Expect Afrobeat performances, global street eats, and shopping from designers who blend traditional prints with modern silhouettes. Held right on the sand, this free fest invites everyone to explore the beauty and brilliance of the continent-and to join in the dancing, drumming, and storytelling as the sun goes down.
Date: August 16
Time: 12PM-8PM
Cost: Free
Location: Ohio Street Beach, 600 N Lake Shore Dr
More Info: eventbrite.com
