June 2026 events calendar for Chicago

The oldest music festival in North America plays host to more than 90 shows throughout summer, featuring big-name headliners like Paul Simon, Alabama Shakes and Chance the Rapper. Check out the full schedule of artists coming to Highland Park this year, and don't forget to pack a picnic.

The Budweiser Concert Series is back at Gallagher Way this summer, with three outdoor shows from Guster, Hippo Campus and Ashley McBryde. GA and VIP tickets are available, and $1 from each ticket sold will go to mental health and wellness organization Backline or sustainability organization Reverb.

From June through September, more than 90 movies will screen in parks across Chicago as part of the Park District's annual Movies in the Parks program. From recent blockbusters like Zootopia 2 and Freakier Friday to classics like Back to the Future and Jumangi, you're sure to find something good to watch (for free!) beneath the stars this summer. Screenings typically begin at 8:45pm, or dusk, each evening. Take a look at the full list of movies and participating parks.

Navy Pier's former Crystal Gardens space is transforming into a retro roller skating rink this summer. Grab your skates and hit the rink for some of the best views in the city, plus an arcade, drinks and groovy disco tunes. At night, the Skate After Dark party turns up the energy for the 21+ crowd with DJ sets on select nights throughout the summer.

Rooftop Cinema Club, the open-air theater perched atop The Emily Hotel, is back for another season. Guests can catch showings of hand-picked classics, cult films and recent releases while also enjoying sweeping views of the skyline and craft beverages. 

Running from May through early November, this season is packed with fresh programming, from curated film collections to immersive themed events like a Singles Night featuring a 90-minute mixer followed by a screening of There’s Something About Mary. 

Heads up, fashion girlies: Reformation is hosting a series of events this month. The "Hot Girls Have Hobbies" series features four themed events, from a game night to a book club, at Reformation shops across the city and will be hosted by local influencers Emily Wittman and Olivia Metzger, and romance book publisher 831 Stories. 

Test your music knowledge on select Tuesday nights with free music bingo at Gallagher Way this summer. Each game covers a different genre, from country and 90s pop to EDM and Broadway. Team sign-up starts at 5:30pm, before the game kicks off at 6pm.

The Chicago Cultural Center is free and open to the public throughout the majority of the year, but if you need an excuse to check out all it has to offer, an Open House should do the trick. This year, the event will feature live music, gallery exhibitions, shopping and more. For a full schedule of activities and to RSVP, visit the official website.

Gallagher Way is showing free outdoor movies on select Wednesday nights through September. From family flicks like Zootopia 2 and High School Musical to classics like How to Lose a Guy in 10 Days and Matilda, there's something for everyone to enjoy. Guests are encouraged to bring a blanket or purchase a VIP or Premier ticket, which includes a reserved seat, snacks and other goodies.

Head to Gallagher Way in Wrigleyville on select Monday evenings throughout the summer to join a free Movement Monday class. This year's lineup includes dance classes, self-defense, yoga and more. Classes are free to attend, but you'll need to reserve a spot in advance.