May 2025 in Chicago is packed with can’t-miss concerts, hilarious comedy, Broadway sensations, and unforgettable live performances. Whether you’re a music lover, theatre fan, or sports enthusiast, this month brings something special for everyone. Explore the city’s vibrant entertainment scene and make the most of your spring in the Windy City!
Unlock Exclusive Savings for Your May Events in Chicago
Enhance your Chicago experience with exclusive discounts, valid for all ticket purchases:
- 5% off orders over $199 – Use code: “take5”
- 10% off orders over $349 – Use coupon code: “take10”
Don’t miss this chance to enjoy incredible entertainment while keeping your budget in check!
The Highlight Reel: Can’t-Miss May Events in Chicago
1. Smallpools
- Date & Time: May 15, 2025, 7:00PM
- Get Tickets: Buy Tickets for Smallpools at House of Blues Chicago
Smallpools, the indie pop band known for their infectious hooks and energetic live shows, brings their Lovetap! 10th Anniversary Tour to House of Blues Chicago. With hits like “Dreaming” and “Karaoke,” Smallpools has earned a loyal fanbase and a reputation for creating feel-good anthems that light up any venue. Their concerts are a celebration of youthful spirit and singalong moments, making this a must-see event for fans of modern pop and alternative music. Expect a night of dancing, nostalgia, and pure fun as Smallpools delivers a show packed with crowd favorites and new surprises.
Get Discounted Tickets & Promo Codes for Smallpools
- 5% off on purchases over $199 in Smallpools Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Smallpools Tickets. Use coupon code: “take10”.
2. Titanique: The Musical
- Date & Time: May 15, 2025, 7:00PM
- Get Tickets: Buy Tickets for Titanique at Broadway Playhouse
Titanique is the musical comedy sensation that reimagines the Titanic story through the music of Céline Dion. This off-Broadway hit sails into Chicago’s Broadway Playhouse with powerhouse vocals, laugh-out-loud moments, and iconic songs like “My Heart Will Go On.” The show blends nostalgia, camp, and pure theatrical joy, delivering a one-of-a-kind voyage that both parodies and pays tribute to the beloved film. If you love big voices, big laughs, and big heart, Titanique is the must-see musical event of the season.
Get Discounted Tickets & Promo Codes for Titanique
- 5% off on purchases over $199 in Titanique Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Titanique Tickets. Use coupon code: “take10”.
3. Jim Jefferies
- Date & Time: May 15, 2025, 7:00PM
- Get Tickets: Buy Tickets for Jim Jefferies at Vic Theatre
Jim Jefferies, the acclaimed Australian comedian, is known for his brutally honest humor and sharp social commentary. With numerous stand-up specials and a hit TV show, Jefferies has built a global following for his fearless takes on politics, culture, and everyday absurdities. His live shows are a rollercoaster of laughter, wit, and sometimes controversy, but always delivered with his signature charm. Catch Jim Jefferies at the Vic Theatre for a night of unfiltered comedy that will leave you thinking and laughing long after the curtain falls.
Get Discounted Tickets & Promo Codes for Jim Jefferies
- 5% off on purchases over $199 in Jim Jefferies Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Jim Jefferies Tickets. Use coupon code: “take10”.
4. Beyoncé
- Date & Time: May 15, 2025, 7:00PM
- Get Tickets: Buy Tickets for Beyoncé at Soldier Field
Beyoncé, the global superstar and multi-Grammy Award winner, returns to Chicago for a spectacular night at Soldier Field. Known for her powerhouse vocals, groundbreaking performances, and chart-topping hits, Beyoncé’s concerts are legendary events that blend music, dance, and visual artistry. From “Crazy in Love” to “Formation,” her setlists are packed with anthems that have defined a generation. Don’t miss this rare opportunity to witness the Queen Bey live, delivering an unforgettable show that will electrify the city and leave fans in awe.
Get Discounted Tickets & Promo Codes for Beyoncé
- 5% off on purchases over $199 in Beyoncé Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Beyoncé Tickets. Use coupon code: “take10”.
5. Benmont Tench
- Date & Time: May 15, 2025, 8:00PM
- Get Tickets: Buy Tickets for Benmont Tench at Garcias Chicago
Benmont Tench, renowned as the founding keyboardist of Tom Petty and the Heartbreakers, brings his signature sound and soulful musicianship to Garcia’s Chicago. Tench’s career spans decades of rock history, contributing to countless classic albums and collaborating with legends across genres. His solo performances showcase his artistry, storytelling, and deep roots in American music. For fans of classic rock, blues, and heartfelt songwriting, this intimate show is a rare treat and a chance to see a living legend up close.
Get Discounted Tickets & Promo Codes for Benmont Tench
- 5% off on purchases over $199 in Benmont Tench Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Benmont Tench Tickets. Use coupon code: “take10”.
6. Bust
- Date & Time: May 16, 2025, 7:30PM
- Get Tickets: Buy Tickets for Bust at Albert Ivar Goodman Theatre
Bust, the daring new play by Pulitzer finalist Zora Howard, takes the stage at Goodman Theatre. This form-defying drama follows a neighborhood thrown into chaos after a police incident goes viral, blending humor, rage, and social commentary. With direction by Lileana Blain-Cruz, Bust explores the limits of community, justice, and what happens when ordinary lives are pushed to the edge. Expect a thought-provoking, laugh-out-loud, and emotionally charged evening of contemporary theatre.
Get Discounted Tickets & Promo Codes for Bust
- 5% off on purchases over $199 in Bust Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Bust Tickets. Use coupon code: “take10”.
7. October London & Tamar Braxton
- Date & Time: May 4, 2025, 7:00PM
- Get Tickets: Buy Tickets for October London & Tamar Braxton at The Chicago Theatre
October London and Tamar Braxton headline the “Calling All Lovers” tour at The Chicago Theatre, joined by special guest Ro James. October London’s smooth, soulful voice and Braxton’s powerhouse vocals promise a night of R&B excellence. Both artists are known for their emotional performances and chart-topping hits, making this show a celebration of love, life, and the unshakable groove of modern soul. Don’t miss this essential experience for any R&B fan.
Get Discounted Tickets & Promo Codes for October London & Tamar Braxton
- 5% off on purchases over $199 in October London & Tamar Braxton Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in October London & Tamar Braxton Tickets. Use coupon code: “take10”.
8. Chicago Cubs vs. San Francisco Giants
- Date & Time: May 5, 2025, 6:40PM
- Get Tickets: Buy Tickets for Cubs vs. Giants at Wrigley Field
Experience the thrill of Major League Baseball as the Chicago Cubs take on the San Francisco Giants at iconic Wrigley Field. The Cubs, with their passionate fanbase and storied history, always deliver excitement on the diamond. Whether you’re a lifelong supporter or a first-time visitor, a Cubs game is a classic Chicago experience filled with energy, tradition, and unforgettable moments. Cheer for the home team and soak up the atmosphere of America’s favorite pastime.
Get Discounted Tickets & Promo Codes for Cubs vs. Giants
- 5% off on purchases over $199 in Cubs vs. Giants Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in Cubs vs. Giants Tickets. Use coupon code: “take10”.
9. Chicago Symphony Orchestra: Mahler’s Symphony No. 6
- Date & Time: May 8, 2025, 7:30PM
- Get Tickets: Buy Tickets for CSO at Chicago Symphony Center
The world-renowned Chicago Symphony Orchestra, led by Jaap van Zweden, presents Mahler’s Symphony No. 6 at Symphony Center. Known for its emotional intensity and sweeping grandeur, Mahler’s Sixth is a showcase for the orchestra’s virtuosity and passion. The CSO is celebrated for its rich sound and artistic excellence, making this performance a must for classical music lovers and anyone seeking a transcendent concert experience in Chicago’s premier venue.
Get Discounted Tickets & Promo Codes for Chicago Symphony Orchestra
- 5% off on purchases over $199 in CSO Tickets. Use coupon code: “take5”.
- 10% off on purchases over $349 in CSO Tickets. Use coupon code: “take10”.
Plan Your Chicago Adventure
From blockbuster concerts and Broadway musicals to world-class sports and comedy, May 2025 in Chicago is bursting with unforgettable experiences. For details and ticket purchases, visit Hunt Tickets and take advantage of exclusive savings!
FAQs for Your Chicago May
- 1. What are some must-see events in Chicago in May?
- Don’t miss Beyoncé at Soldier Field, Titanique, Smallpools, Jim Jefferies, and the Cubs vs. Giants at Wrigley Field.
- 2. Where can I buy tickets for these events?
- Tickets are available through Hunt Tickets and other major ticketing platforms.
- 3. Are there events accessible in downtown Chicago?
- Absolutely! Many of these shows and games are in the heart of the city, easily accessible by public transit or car.
From thrilling concerts to captivating theatre and sporting events, May events in Chicago have something for everyone. Don’t miss out—secure your tickets and enjoy the best of the Windy City!