August in Chicago: Our Favorite Summer Happenings!
As local real estate brokers who love Chicago, we think of summer as when our city truly shines—and August is packed with events that show off the best of our neighborhoods, culture, and community. If you're new to the area, considering a move, or just looking to fall a little more in love with Chicago, here are a few of my favorite August highlights:
Fiesta del Sol (July 31–August 3): A vibrant celebration of culture and community in the heart of Pilsen, featuring live music, authentic food, local art, and family-friendly activities. This annual event captures the spirit and diversity of the neighborhood with a festive, welcoming atmosphere.
Lollapalooza (July 31–August 3): One of the biggest music festivals in the U.S., Lollapalooza takes over Grant Park for four days of nonstop performances across multiple genres. The 2025 lineup features headliners Tyler, the Creator, Luke Combs, Olivia Rodrigo, Korn, TWICE, RÜFÜS DU SOL, Sabrina Carpenter, and A$AP Rocky, with supporting acts like Gracie Abrams, Doechii, T-Pain, Clairo, Foster the People, and Dominic Fike.
Chicago Ducky Derby (August 7): A beloved charity event where thousands of rubber ducks race down the Chicago River to raise money for Special Olympics Illinois. Family-friendly and full of fun.
Bud Billiken Parade & Picnic (August 9): The largest African American parade in the U.S., celebrating education and community with lively marching bands, dance teams, and cultural pride. It kicks off the back-to-school season in style.
Fan Expo Chicago (August 15–17): A major pop culture convention where fans can meet stars like Ewan McGregor, Orlando Bloom, and Hayden Christensen. Includes celebrity panels, cosplay contests, collectibles, gaming, and more.
UFC 319 (August 16): A thrilling middleweight title fight between Dricus du Plessis and Khamzat Chimaev, sure to be one of the year’s biggest UFC showdowns.
Navy Pier’s Great American Lobster Fest (August 16–17): The Midwest’s largest seafood festival serves up fresh lobster, live music, drinks, and lakefront views at Navy Pier.
Chicago Air and Water Show (August 16–17): A jaw-dropping lakefront spectacle featuring military and civilian aircraft, stunt pilots, and parachute teams soaring above the city skyline.
Chicago House Music Festival & Conference (August 21–24): A celebration of Chicago’s iconic house music genre with live DJ sets, dance showcases, and industry panels. Lineup TBA, but expect top local and global talent.
Taste of Greektown (August 22–24): A lively street festival filled with authentic Greek food, live music, and traditional dancing in the heart of Chicago’s historic Greektown neighborhood.
Chicago Triathlon (August 23): One of the world’s largest triathlons, drawing elite athletes and amateurs to swim, bike, and run along the scenic Chicago lakefront.
Chicago Jazz Festival (August 28–31): A free, citywide celebration of jazz, showcasing artists like Esperanza Spalding, Monty Alexander, Kermit Ruffins, and Eliades Ochoa, alongside Chicago legends like Patricia Barber and Ernest Dawkins.
North Coast Music Festival (August 28–31): Chicago’s premier EDM festival at SeatGeek Stadium features a stacked lineup including Chris Lake, deadmau5 (Drum & Bass set), Excision, Rezz, Kaskade, Seven Lions, Zedd, Sofi Tukker, Galantis, and more for three nights of immersive music and visuals.