May 2025 events calendar for Chicago

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 October, this season is packed with fresh programming, from curated film collections to immersive themed events like a Wicked singalong (break out those brooms!); a Mamma Mia! girls' night out event (complete with karaoke, mini makeovers and swag bags); a Pride-ready airing of The Birdcage along with a live drag show; and Wine Wednesdays in partnership with Bucket Listers—and, yes, your ticket includes a glass of vino!

Wrigley Field-adjacent plaza Gallagher Way is once again showing free outdoor movie screenings this summer. Admission is free and attendees are welcome to bring their own food, enjoy on-site concessions or snag a meal from nearby restaurants like Big Star and Smoke Daddy. VIP seating is also available—check out the Gallagher Way website for more details. Gates open at 6pm for each screening and the movies start at 7:30pm.

• May 21: Hook
• June 4: Twisters
• June 11: The Parent Trap
• June 25: Inside Out 2
• July 9: Wicked
• July 16: Top Gun: Maverick
• July 30: The Little Mermaid
• August 13: Moana 2
• August 27: Crazy Rich Asians
• September 10: Space Jam
• September 17: Remember the Titans

During the summer, one of the best aerial displays you'll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

Every night in our dreams, we've wished for this moment: Titanique the Musical is cruising into Chicago! The smash-hit comedy, in which "the music of Céline Dion makes sweet Canadian love with the film Titanic," is gearing up for a Chicago run as a co-production from Porchlight Music Theatre and Broadway in Chicago, with performances set for the Broadway Playhouse at Water Tower Place this spring. 

Led by actress Clare Kennedy McLaughlin, who will play the French-Canadian pop diva herself, Chicago's Titanique will retell the fictionalized story of Titanic's sinking from James Cameron’s 1997 Blockbuster, albeit using Dion's famous power ballads to push the plot forward. Featured tunes include “Because You Loved Me,” “All By Myself,” “To Love You More,” “Tell Him,” “Beauty and the Beast" and two of Dion's most-loved covers, “River Deep, Mountain High” and “I Drove All Night," culminating, of course, in that radio juggernaut “My Heart Will Go On.” 

For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.

You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.