What is it? The Grant Park Music Festival is a free, 10-week outdoor classical music series held every summer in Chicago’s Millennium Park, primarily at the Jay Pritzker Pavilion. Running from June 11 to August 16, 2025 , the festival features performances by the acclaimed Grant Park Orchestra and Chorus , along with world-renowned guest artists and conductors. With concerts happening most Wednesdays, Fridays, and Saturdays, the season includes standout pieces like Carmina Burana, Rhapsody in Blue, Boléro, and performances by violinist Joshua Bell . Seating on the Great Lawn and in parts of the Seating Bowl is free and first-come, while membership options are available for reserved seating.

What is it? Windy City Smokeout 2025 is a four-day outdoor festival happening July 10–13 outside the United Center in Chicago. It combines top country music performances with award-winning BBQ from renowned pitmasters across the country. Headliners include Bailey Zimmerman, Old Dominion, Kane Brown, and Jon Pardi, along with a stacked lineup of rising stars and a special Sunday brunch performance. The event is family-friendly, ADA-accessible, and offers multiple ticket tiers including General Admission, VIP, and Platinum. Food, drinks, live music, and good vibes take over Lot C for one of Chicago’s biggest summer parties.

Dates : Saturday, June 21 & Sunday, June 22, 2025

Location: St. George Greek Orthodox Church, 2701 N. Sheffield Ave., Chicago

Beyond Wonderland Chicago returns June 7–8, 2025, at Huntington Bank Pavilion on Northerly Island, featuring headliners like Illenium, Marshmello, Afrojack, SLANDER, and MEDUZA across four immersive stages . The festival runs from 2 PM to 11 PM daily, with no re-entry allowed . Tickets are still available: 2-day GA passes are $209.98, GA+ (with expedited entry and premium restrooms) are $279.98, and VIP passes (with exclusive viewing areas and lounges) are $369.98 . Attendees must be 18+ (21+ for alcohol and VIP), and clear bags are required for entry .

Sueños Music Festival 2025 takes place May 24–25 in Chicago's Grant Park, featuring Latin music stars like Shakira, Don Omar, Peso Pluma, and Grupo Frontera across two stages. With over 30 artists, expanded festival grounds, and ticket options ranging from GA to VIP, it's one of the largest Latin music events in the U.S. Passes are nearly sold out and available on the official Sueños website.

ART on THE MART is the world’s largest permanent digital art projection, lighting up the 2.5-acre façade of Chicago’s THE MART with contemporary artwork. The Spring 2025 program runs Thursdays through Sundays, 8:30–9:00 PM, from April 25 to July 6, best viewed from the Chicago Riverwalk. Featuring immersive visuals and audio, it showcases works from both global and local artists.

Beyoncé is bringing her Cowboy Carter Tour to Chicago’s Soldier Field this weekend with shows on May 15, 17, and 18, starting at 7 PM. Tickets are still available on Ticketmaster, StubHub, Vivid Seats, and SeatGeek, with prices starting around $109. The show features a genre-blending setlist, family appearances, and celebrates her latest album with a country-pop fusion. Fans can also enjoy Beyoncé-themed events across the city, including a bar crawl, immersive pop-ups, and special installations.

Chicago Cabaret Week 2025 runs from May 9–18 and celebrates the city’s dynamic cabaret scene. The festival features over 95 performers at 17 venues across Chicago and the suburbs, showcasing blues, Broadway, burlesque, jazz, R\&B, French chanson, and world music. It’s a unique chance to experience Chicago’s rich musical and theatrical talent in intimate settings.