May 2025 events calendar for Chicago

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 8:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

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

Bingo Loco, an interactive rave show that takes place in cities around the world, comes to West Loop’s Morgan MFG this spring, with five dates in Chicago (March 28, April 11, April 25, May 10 and May 23.) The traditional game of bingo gets reimagined as a three-hour long immersive experience, complete with epic dance offs, rave rounds, lip sync battles, confetti showers, CO2 cannons, conga lines and prizes ranging from international trips to lawnmowers. One thing’s for sure—this ain’t bingo night at the senior center.

Started in 2022, this two-day extravaganza returns to Grant Park over Memorial Day weekend. Taking place on a single stage in Grant Park's Hutchinson Field, Sueños will feature headlining sets from Peso Pluma, Shakira, Don Omar, Grupo Frontera, Archangel, Bellakath and more 

In addition to two days of music, you can try food from some of Chicago's best Latin restaurants, a host of art installations and experiential activations, and a Ferris wheel in the park that you can ride between (or during) sets. It's one of the largest new festivals to come to launch in Chicago in years and a fitting addition to a summer festival calendar that's more crowded than ever.

Whether you like your hot dogs dragged through the garden or topped with ketchup, this Portage Park fest has you covered. Local favorites, including Byron's Hot Dogs, Baked Cheese Haus, Chicago Doghouse, Frannies, Lee Concessions, Tikka Masala Dogs and Sausage Fest Food Truck, will compete to see who makes the best frankfurter, as voted on by fest-goers. In addition, there will be live entertainment, arts and craft vendors, a kids area, a top dog parade and a hot dog eating competition.

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Attendees can explore the five Festival Days, full days of programming in a given neighborhood, including in Lakeview on April 27, in Bridgeport on May 10, in Lincoln Park on May 18, and at the Art Institute of Chicago on June 7, as well as thought-provoking discussions and exciting live performances sprinkled throughout the schedule. 

Some of the fest’s biggest speakers this season include Broadway star Leslie Odom, Jr., beloved comedian Ed Helms, artist Tonika Lewis Johnson, musicians like Jon Batiste and Jim Jaramusch, podcaster Ezra Kein, TV icon Paul Reiser, bestselling author Ron Chernow and more. You can see a full schedule of programming on the Chicago Humanities Festival website.

Pilsen's annual Mole de Mayo street festival—which honors the traditional Mexican sauce with a mole cook-off, plus a market full of vendors—is back this Memorial Day weekend, taking over the stretch of 18th Street between Morgan and Halsted from Saturday, May 24 through Monday, May 26. Grab some enchiladas smothered in aromatic mole and don't miss the festival's lucha libra wrestling matches. A Children’s Zone will present games, arts and crafts and interactive activities for the kiddos.

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.