June 2026 events calendar for Chicago

Chicago Pride Fest brings two days of music, drag, vendors and LGBTQ-friendly event to Northalsted in celebration of Chicago Pride Month. Swing by to catch headlining sets from major chart-topping and local artists. Plus, browse arts and crafts from more than 150 vendors and don't miss out on the Proud Pet Parade at noon on Sunday. Once you've had your fill, head to one of the best gay bars in Chicago to keep the party going.

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.

Pepsi is taking over Big Star in Wicker Park through its Local Eats Deserve Pepsi platform. TV star Dylan Efron will make an appearance to celebrate the taco dish he created in collaboration with the restaurant. The event is free to attend, and guests can expect free food and performances by country artist Lauren Watkins and DJ JayFunk.

Celebrate Pride with the whole family at OUT at Gallagher Way. The free all-day event features face painting, balloon artists, bracelet-making, giveaways and Voguing classes, plus performances by the Chicago Gay Men's Chorus and Rock and Roll Playhouse.

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.