Events in May in Chicago

• Sat, 09 May, 2026 - 12:00 PM

  FREE Community Pop-up Thrift Boutique

  Mindy Blanco: Allstate Insurance

  Free
• Sat, 02 May, 2026 - 08:00 PM

  Calum Scott in Chicago

  Riviera Theatre
• Sat, 09 May, 2026 - 07:30 PM

  The CBASO & the CBA Chorus in Concert at St James Cathedral

  65 E Huron St

  USD 18
• Fri, 01 May, 2026 - 08:00 PM

  Demi Lovato: It's Not That Deep Tour

  United Center

  420+ Interested
• Fri, 15 May, 2026 - 08:00 PM

  Timmy Trumpet at Salt Shed - Indoor Shed

  Salt Shed - Indoor Shed
• Sat, 23 May, 2026 - 06:00 PM

  SLIDE AWAY 2026

  Byline Bank Aragon Ballroom

  185+ Interested
• Tue, 19 May, 2026 - 09:00 AM

  DigiMarCon Midwest 2026 - Digital Marketing Conference & Exhibition

  Soldier Field Stadium

  USD 102
• Sun, 03 May, 2026 - 03:00 PM

  Chicago Artopia Presents: Tango 21 Dance Theater

  Balzekas Museum Of Lithuanian Culture, South Pulaski Road, Chicago, IL, USA

  Free
• Fri, 22 May, 2026 - 06:00 PM

  Suenos Music Festival - 2 Day Pass

  Hutchinson Field Grant Park
• Sat, 02 May, 2026 - 07:00 PM

  Matteo Lane at Chicago Theatre

  Chicago Theatre
• Sat, 02 May, 2026 - 06:00 PM

  Kim La’Chelle’s 60th Diamond Jubilee 💎

  Downtown Chicago

  73+ Interested
• Sat, 02 May, 2026 - 07:00 PM

  Katt Williams Chicago

  KATT WILLIAMS – Chicago, IL – May 2, 2026

  49+ Interested
• Sat, 30 May, 2026 - 06:00 PM

  Chris L. McKenna and Rory Gibson Chicagoland Private Dinner

  The Chicagoland Area

  12+ Interested
• Sat, 02 May, 2026 - 08:00 PM

  Katt Williams: The Golden Age Tour

  United Center

  4389+ Interested
• Sat, 09 May, 2026 - 12:00 PM

  Paddlers Guide to Safety : Jackson Park Yacht Club

  Jackson Park Yacht Club

  Free