A Month of Merriment and Mayhem: A Chicago Entertainment Odyssey – May 2025

The vibrant city of Chicago in May 2025 is poised to deliver a captivating tapestry of entertainment, predominantly woven with threads of laughter and theatrical improvisation. This month’s schedule, rich with comedic talent and spontaneous performances, offers a diverse range of experiences for those seeking an escape from the mundane. From the intimate setting of comedy clubs to the grand stages of iconic theaters, Chicago’s entertainment scene promises a month filled with memorable moments. Let’s delve into this exciting lineup, highlighting some of the performers and venues that will be setting the stage for a month of merriment and perhaps a touch of delightful mayhem.

The month kicks off with a strong comedic presence at Zanies Comedy Club in Chicago. From May 1st to May 3rd, the sharp wit of Laura Peek will grace the stage. Known for her observational humor and relatable storytelling, Peek’s multiple shows throughout the weekend offer ample opportunity to catch her engaging comedic style. Her performances, with ticket prices starting at $60, promise an evening of genuine laughs in the classic comedy club atmosphere.

Adding to the opening night’s comedic offerings at Zanies on May 1st is the ever-unpredictable Roast Battle. While the specific performers in each battle vary, this format guarantees a night of sharp and often hilarious comedic sparring, with tickets starting at $132.

Meanwhile, the Io Theater in Chicago starts the month with its signature blend of improv and sketch comedy. On May 1st, audiences can catch Beverly – A Bevy Show, promising a unique and likely hilarious take on the improv format. Tickets for this show start at $28. The Io Theater, a breeding ground for comedic talent, continues its offerings throughout the weekend with Escandalo on May 2nd and May 9th, a show that hints at a lively and perhaps chaotic performance, with tickets from $51.

The first Saturday of May, May 3rd, sees a surge of comedic star power across various Chicago venues. In addition to Laura Peek’s continued run at Zanies, the Vic Theatre welcomes the seasoned comedic presence of Bruce Bruce. With two shows scheduled for the evening (7:00 PM and 9:30 PM), Bruce Bruce’s energetic and often improvisational style, with tickets starting from $16, is sure to have the audience roaring with laughter.

Also on May 3rd, the iconic Riviera Theatre will host the legendary Eddie Griffin. Known for his sharp social commentary and unapologetic delivery, Griffin’s performance, with tickets starting at $97, is undoubtedly a highly anticipated event. His long and successful career speaks volumes about his comedic prowess, promising a night of thought-provoking and hilarious observations.

Adding to the Saturday night entertainment on May 3rd is Heather McMahan at The Chicago Theatre. McMahan, known for her relatable and often self-deprecating humor, brings her unique brand of comedy to a larger stage, with tickets starting at just $9. Her engaging personality and witty anecdotes have garnered a significant following, making this a potentially popular show.

The comedic momentum continues into Sunday, May 4th, with Doug Benson bringing his laid-back and often cannabis-themed humor to Zanies Comedy Club for a special 4:20 PM show, with tickets starting at $56. Benson’s relaxed delivery and witty observations have made him a favorite among comedy enthusiasts. Meanwhile, the Io Theater will present its regular Harold Night, a showcase of long-form improv, offering audiences a chance to witness the spontaneous creativity of Chicago’s improv scene, with tickets from $46. The Theater 3 Mainstage At The Lincoln Lodge offers a different kind of Sunday entertainment with You Win Some, You Dim Sum, a show that promises a unique blend of performance and perhaps even culinary delights, with tickets starting at $32.

The beginning of the week, May 5th, sees Jack Jr. taking the stage at Zanies Comedy Club, with tickets starting at $60, likely bringing a fresh comedic perspective to the venue. Over at the Io Theater, Monday night features Blast!, an energetic improv show featuring the talents of the Io ensemble, with tickets from $40.

Mid-week, on May 7th, City Winery – Chicago offers a different comedic flavor with Bad Momz of Comedy, a show featuring a rotating cast of hilarious mothers sharing their experiences, with tickets starting at $56. The Io Theater continues its diverse programming on the same night with People Presenting Things and Sketch Playlist, offering a mix of structured sketch comedy and potentially quirky presentations, both with tickets starting at $51.

The second weekend of May brings another wave of comedic talent. Zoltan Kaszas will be headlining at Zanies Comedy Club from May 8th to May 11th, with multiple shows each night. Kaszas is known for his clever writing and engaging stage presence, making his multiple performances a highlight of the weekend. Ticket prices for his shows vary, starting from $60 and going up to $132 for some performances.

Adding to the Saturday night lineup on May 10th, Ali Siddiq will be performing at The Chicago Theatre. Siddiq’s comedic style often incorporates his life experiences with sharp wit and insightful observations, promising a compelling and funny performance, with tickets starting at $54. The Io Theater will offer Improvised Jane Austen on May 10th and May 17th, a unique comedic experience that blends the elegance of Austen’s world with the spontaneity of improvisation, with tickets from $67. The same venue will also host Binge the Fringe on May 10th, promising a taste of the eclectic and experimental performances often found at fringe festivals, with tickets from $51.

Beyond the headliners, various venues continue to offer a diverse range of entertainment:

• Io Theater:
  • May 8th: Beverly – A Bevy Show (From $28)
  • May 9th: Escandalo (From $51)
  • May 11th: Harold Night (featuring various Io Theater performers) (From $46)
  • May 12th: Blast! (featuring the Io Theater ensemble) (From $40)
  • May 13th: Freak of the Week: 2 Dead Ass Hoes (likely featuring a comedic duo) (From $30)

The Beat Kitchen on May 9th offers a musical interlude with the band Vial, with tickets starting at $37, providing a change of pace from the predominantly comedic offerings.

The middle of May continues with more comedic highlights. Debra DiGiovanni, known for her sharp and often self-deprecating humor, will be at Zanies Comedy Club on May 14th, with tickets starting at $60. Her engaging storytelling and quick wit are sure to entertain. The Io Theater on the same night offers The Gist – An Improvised Sketch Show and Family – An Improv Show, providing further opportunities to witness the unpredictable and hilarious nature of improv, with tickets from $35 and $46 respectively.

May 15th brings a significant comedic force to the Vic Theatre with Jim Jefferies. Known for his controversial yet insightful takes on social and political issues, Jefferies’ performances (also on May 16th with multiple shows) are highly anticipated, with ticket prices starting from $56. His no-holds-barred style of comedy has earned him a dedicated following. The Beat Kitchen on the same night offers a different kind of entertainment with Kyle Gordon, with tickets starting at $49, potentially a musical or comedic act with a unique style. Zanies Comedy Club on May 15th and 16th will also feature Cy Amundson, offering his comedic stylings with tickets starting at $60. Additionally, Zanies will host another Roast Battle on May 15th, with tickets from $56.

• Zanies Comedy Club (May 17th): Cy Amundson (From $60)
• Io Theater (May 16th): Escandalo (From $51)
• Io Theater (May 17th): Improvised Jane Austen (From $67)

Sunday, May 18th, at Zanies Comedy Club features Laila Roth, promising a different comedic voice. The Io Theater on the same night presents the Asian Persuasion Comedy Variety Show, featuring a lineup of talented Asian-American comedians. Thalia Hall on May 18th offers a different kind of comedic duo with Two Dykes and a Mic, featuring comedians Rachel Scanlon and Caroline Rose, suggesting a potentially bold and boundary-pushing performance.

The week of May 19th starts with the familiar Blast! at the Io Theater, featuring the Io ensemble. May 20th sees the return of Freak of the Week: 2 Dead Ass Hoes at the same venue, likely featuring the comedic duo behind the show. May 21st brings Tommy Ryman to Zanies Comedy Club, likely offering his brand of observational or storytelling humor. The Theater 1 Brown Room At The Lincoln Lodge on the same night hosts The Popout Comedy Show, promising a surprise lineup of Chicago comedic talent. The Io Theater on May 21st also features Family – An Improv Show.

The latter part of May is equally packed with comedic talent. Casey Balsham will be performing at Zanies Comedy Club from May 22nd to May 23rd, likely bringing her unique comedic perspective to the stage. On May 22nd, The Chicago Theatre welcomes the highly popular Nikki Glaser for two shows. Known for her sharp wit, honest and often raunchy humor, and engaging stage presence, Glaser’s performances are sure to be a major draw. Zanies on May 22nd also features Chris Andrade, offering his comedic stylings, and the Io Theater will have Sketch Playlist on the same night.

• Zanies Comedy Club (May 24th): Andre Kim (Multiple Shows)
• Io Theater (May 23rd): Escandalo (From $51)
• Io Theater (May 24th): Improvised Jane Austen (From $67)

Sunday, May 25th, at Zanies features Manuel Angel Redondo, while the Io Theater will host its regular Harold Night, featuring the resident improv team. Park West on May 25th offers a performance by Yohay Sponder, though details are limited.

The final week of May continues the comedic journey. May 26th features Blast! at the Io Theater, showcasing the talents of their improv ensemble. May 28th brings international comedy to Thalia Hall with Urzila Carlson, known for her energetic and observational humor. The Io Theater on the same night will have Family – An Improv Show.

• Zanies Comedy Club (May 29th – May 31st): Justin Silva (Multiple Shows)
• Io Theater (May 29th): Bluebird Improv (Multiple Shows)
• City Winery – Chicago (May 29th): Two Jews Comedy (featuring comedians Ashley Gutermuth and Wendy Liebman)
• Io Theater (May 30th): Escandalo
• The Chicago Theatre (May 30th): Matt Mathews
• Io Theater (May 31st): Improvised Jane Austen
• The Chicago Theatre (May 31st): Nikki Glaser (Two Shows)

This extensive schedule highlights Chicago’s vibrant and diverse entertainment scene in May 2025. The strong emphasis on comedy, ranging from established headliners to local improv troupes and unique variety shows, ensures that there will be something to tickle everyone’s funny bone. The variety of venues, from the intimate setting of Zanies and the Io Theater to the grand stages of The Chicago Theatre and the Vic Theatre, adds to the richness of the offerings. Whether you’re a fan of stand-up, improv, sketch comedy, or even a musical interlude, Chicago in May promises a month filled with laughter, spontaneity, and unforgettable performances. Remember to check the provided links for the latest ticket information and showtimes, and prepare for a month of entertainment that will leave you smiling long after the final curtain falls.