Events and Things to Do in Chicago, IL

Saturday, June 20

Featured

The Art of Life Gala

JUN

20

6:00 PM

1029 W 35th St, Chicago, IL

Join us for an immersive experience bringing together art, live music, and health advocacy to raise awareness and support for...

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Saturday, May 23

• Come See All About The Benjamins on Saturday, May 23, 2026, At Rooftop Cinema Club 10:45 pm

  Rooftop at The Emily Hotel, 311 N Morgan St 5th Floor, Chicago, IL 60607

  
  

Sunday, May 24

• 41st Annual Belmont-Sheffield Music Fest 9:00 am

  3200 N Sheffield Ave, Chicago

  
  
• Randolph Street Market Festival returns for its 2026 season, kicking off May 23–24 with the 23rd ann 10:00 am

  1341 W Randolph St, Chicago

  
  
• Hyatt Lodge Oak Brook hosts Memorial Day weekend celebration with Sunday’s Bike the Reserve 10:00 am

  Hyatt Lodge Oak Brook Chicago, 2815 Jorie Blvd, Oak Brook

  
  
• Come See The Princess Diaries on Sunday, May 24, 2026, At Rooftop Cinema Club 11:00 am

  Rooftop at The Emily Hotel, 311 N Morgan St 5th Floor, Chicago, IL 60607

  
  
• Come See Goat on Sunday, May 24, 2026, At Rooftop Cinema Club 2:00 pm

  Rooftop at The Emily Hotel, 311 N Morgan St 5th Floor, Chicago, IL 60607

  
  
• Come See Baby Boy (2001) on Sunday, May 24, 2026, At Rooftop Cinema Club 8:00 pm

  Rooftop at The Emily Hotel, 311 N Morgan St 5th Floor, Chicago, IL 60607

  
  
• Come See Crazy, Stupid, Love on Sunday, May 24, 2026, At Rooftop Cinema Club 11:00 pm

  Rooftop Cinema Club Fulton Market, 311 N Morgan St, Chicago

  
  

Tuesday, May 26

• Plant Repotting 101 with BCollective 5:30 pm

  Alma, 3630 N Clark St, Chicago

  
  
• Belle Tire helps drivers prepare for Memorial Day weekend and summer road travel with new tire and c 8:00 pm

  Belle Tire, 3225 W North Ave, Melrose Park

  
  

Wednesday, May 27

• Live music at Boleo Chicago 6:00 pm

  Boleo, 122 W Monroe St, Chicago

  
  

Thursday, May 28

• The Pink Affair 12:00 pm

  9119 S Exchange Ave, Chicago

  
  
• UChicago Catering Showcase Featuring Love Local Partners & A Sneak Preview of Bahama Shack 4:00 pm

  1452 E 53rd St, Chicago

  
  
• Mariano's Burger Smash with Chef Lamar Moore! 7:00 pm

  Mariano's, 40 S Halsted St, Chicago

  
  
• Stygian Bough 8:00 pm

  Reggies Chicago, 2105 S State St, Chicago

  
  

Friday, May 29

• The Art of the French Girl Makeup Look 4:00 pm

  Sofitel Chicago Magnificent Mile, 20 E Chestnut St, Chicago

  
  
• Come See How to Lose a Guy in 10 Days on Friday, May 29, 2026, At Rooftop Cinema Club 5:00 pm

  Rooftop at The Emily Hotel, 311 N Morgan St 5th Floor, Chicago, IL 60607

  
  
• Wine Fest on the Beach - Wine Tasting at North Ave. Beach 6:00 pm

  Shore Club Chicago, 1603 N Jean Baptiste Pointe du Sable Lake Shore Dr, Chicago

  
  
• Candlelight: 90s Hip-Hop on Strings 6:30 pm

  Arts Center, 200 N Oak Park Ave, Oak Park

  
  
• Candlelight: Tribute to Taylor Swift 6:30 pm

  Stan Mansion, 2408 N Kedzie Blvd, Chicago