Benable — create shareable lists of things you recommend!
E.g., products you love, local businesses, travel recs - you can add anything to a Benable list!
Events starting in Downtown Chicago June/2025.
16
items Chicago in the summer is when the city truly comes alive. The lakefront shimmers with activity, parks transform into concert venues, and every corner feels electric with culture, food, and music. With warm breezes off Lake Michigan and skyline views ...
Three days of top-tier blues on the Jay Pritzker Pavilion in Millennium Park. Expect headliners like Christone “Kingfish” Ingram with free general admission seating opening at 2 pm daily.
Chicago Blues Festival
A week-long festival spotlighting cutting-edge physical theater, dance, and performance art across venues in the Loop .
Physical Theater Festival
Citywide culinary activations—from pop-ups and panels to charity dinners—culminating in the awards ceremony on June 16 at the Lyric Opera House.
James Beard Awards events
Joffrey Ballet: Alice’s Adventures in Wonderland (through June 22)
A whimsical and modern tap-infused ballet interpretation at the Lyric Opera House.
Alice's Adventures in Wonderland
Lakefront cruises with star performances (launching June 8 with Sister Hazel’s Ken Block and Drew Copeland); options include VIP passes with dinner/drinks.
City Cruises Live is bringing live entertainment to the water!
Heavyweight, Light Heavyweight & Middleweight MMA semifinals at Chicago’s Wintrust Arena.
Professional Fighters League
Summer Music Series: Mondays & Thursdays, Jun 26–Aug 7 at Jay Pritzker Pavilion .
Summer Film Series: Tuesdays starting July 1 (tuesdays through August) .
Grant Park Music Festival: Free classical concerts Wed/Sat/Sun, June through August.
Millennium Park
Monthly open-air market on select Sundays (June 8, July 13, Aug 10) in the Bridgeport area.
Maxwell Street
Navy Pier, 600 E Grand Ave
Free fireworks shows all summer:
Wednesdays at 9PM
Saturdays at 10PM
🎶 Often synced to music. Great to pair with a dinner cruise or Ferris wheel ride.
Fireworks
Flight of Butterflies Art Installation – butterfly sculptures on the Magnificent Mile and Grant Park, now through Sept 2025.
Flight of Butterflies | 07/21/2024
Chicago Architecture River Cruises – ideal downtown riverwalk activity on warm evenings.
Chicago River Boat Architecture Tours
Summer Tequila Tasting Festival (July 26): Sample 20+ tequilas/mezcals with live DJs and bites. 
Chinatown Summer Fair & Chosen Few Picnic: Culture, cuisine, dance, and lakefront house music.
2025 Chicago Summer Tequila Tasting Festival
Lollapalooza
Four days of headliners in Grant Park—with big names like Tyler, The Creator, Olivia Rodrigo & Sabrina Carpenter gracing 8 stages.
Lineup | Lollapalooza | July 31 – August 3, 2025
August: Air & Water Fun
Chicago Air & Water Show (mid‑August): Free acrobatic flybys, parachute teams, and waterfront excitement along Lake Michigan.
Chicago Air and Water Show | Aug. 16 – 17, 2025 | Official Guide & Where to Watch
Bud Billiken Parade & Picnic (Aug 9): Chicago’s iconic African‑American parade and celebration on MLK Drive.
Bud Billiken Parade
September: Food, Flavors & Final Festivals
Taste of Chicago (early Sept): Chicago’s signature food fest with cuisine from top restaurants along the lakefront.
Chicago Jazz Festival continues into early September.
Riot Fest (mid‑Sept, Douglass Par...
Taste of Chicago | Sept. 5 – 7, 2025 | Restaurants & Concerts