Summer technically starts June 20 … but we know Summertime Chi is already in full swing. Get out there!
🌭 Street Fests
- Do Division: May 30-June 1
- Windy City Hot Dog Fest: May 30-June 1
- Ribfest: June 6-8
- 57th Street Art Fair: June 7-8
- Andersonville Midsommarfest: June 13-15
As always, Chicago is hosting some fun free street fests but don’t forget to donate at the gate!
🎶 Free Blues Music
- Chicago Blues Festival in Millennium Park: June 5-8
- Record Row Concert Series: June 5, 12, 18, 19, 26
Most Chicagoans know about the Blues Festival, but the Record Row Concert Series offers another free option on Thursday nights throughout the summer. It’s hosted by Willie Dixon's Blues Heaven Foundation — one of Chicago’s most unique museums.

Kids enjoying the Puerto Rican People’s Parade in 2022. (risingthermals / Flickr)
🇵🇷 Puerto Rican People’s Parade and Festival
- The Parade: June 14
- The Festival: June 12-15
We know the Puerto Rican celebration is here when the flags start flying from cars. This year, the 47th annual parade kicks off at 2 p.m. on Division and California. The fun goes on for four days in Humboldt Park. Festival admission is free on Thursday and costs $15+ over the weekend.
🏳️🌈
Chicago Pride
- Pride Fest: June 21-22
- A two-day street fest in Northalsted the weekend before the big parade, featuring live music on three stages, drag performances, 150+ vendors, and more. Headliners include Jesse McCartney and Deborah Cox.
- Pride Parade: June 29
- Last year, the Pride Parade was shortened to a two-mile route. This year, the parade follows that same path, starting on Sheridan and Broadway at 11 a.m.
Whether you’re at the official Pride events or not, expect Northalsted to be a non-stop party this month. Get ready, and try not to trip on the discarded feather boas. There’s also Backlot Bash in Andersonville the weekend of the parade. And yes, Jojo Siwa is performing.
🎥 Free Movies
- For the kids: There are 40 family movie screening at parks throughout Chicago during June, plus three screenings outside of Wrigley Field at Gallagher Way.
- For the grown-ups: Summer Screenings, hosted at the Chicago Cultural Center and the Chicago History Museum, kick off June 2 and are entirely free to the public. They feature flicks from around the world, and this season’s theme is Summer of Love.
🏙️ Enjoy the Riverwalk
- Hear free live music at Tiny Tapp & Tiny Cafe on select days from now until early October.
- Catch Art on the Mart projections on the side of Merchandise Mart, perfectly visible from the south side of the river. Animated projections run from 9-9:30 p.m., Thursday through Sunday, beginning June 6.
Don’t forget: There are lots of ways to enjoy the river this summer 🛶



