Events and Things to Do in Chicago, IL

Sunday, September 20

Featured

Galli Lucha Libre at Avondale Music Hall

SEP

20

5:45 PM

Avondale Music Hall, 3342 N Milwaukee Ave, Chicago, IL

Experience the high-flying excitement of live lucha libre wrestling featuring an incredible lineup of stars including Hijo De...

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Friday, September 25

Featured

Free Bra Fittings to Support Breast Cancer Awareness

SEP

25

10:00 AM

Von Maur, 3810 E Main St, St. Charles, IL

Join Wacoal for Fit for the Cure®, a special in-person event that combines expert bra fittings with meaningful impact in the...

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Wednesday, September 30

Featured

ProPulse | From Industry Legacy to Workforce Intelligence

SEP

30

3:00 PM

The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL

ProPulse 2026 is ProGlove's flagship industry event, bringing together operations leaders, IT decision makers, and innovation...

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Thursday, October 1

Featured

Free Bra Fittings to Support Breast Cancer Awareness

OCT

1

10:00 AM

Von Maur, 4 Orland Square Dr, Orland Park, IL

Join Wacoal for Fit for the Cure®, a special in-person event that combines expert bra fittings with meaningful impact in the...

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Saturday, October 17

Featured

The Wellness Retreat: A Festival Where Mind, Body, and Music Meet

OCT

17

11:00 AM

Chicago, IL

FEATURING ELDERBROOK LIVE AT SUNSET The Wellness Retreat is taking over Chicago’s Northerly Island for one unforgettable day of...

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Thursday, September 17

• Sketch Playlist 9:30 pm

  The iO Theater, 1501 N Kingsbury St, Chicago

  
  

Friday, September 18

• National Guacamole Day at Blanco Cocina + Cantina 11:00 am

  Blanco Cocina + Cantina, 2022 Spring Rd, Oak Brook

  
  
• Barrio Celebrates National Guacamole Day 4:00 pm

  Barrio, 65 W Kinzie St, Chicago

  
  
• 31st Annual Retro on Roscoe Fest 5:00 pm

  2000 W Roscoe St, Chicago

  
  
• Candlelight: Tribute to Michael Jackson 6:30 pm

  Arts Center, 200 N Oak Park Ave, Oak Park

  
  
• Candlelight: Vivaldi's Four Seasons 8:45 pm

  Arts Center, 200 N Oak Park Ave, Oak Park

  
  
• Broadway Rave 9:00 pm

  Subterranean, 2011 W North Ave, Chicago

  
  

Saturday, September 19

• Glitz, Glam & Giving Back: Divas® Running Series Returns to Chicago 7:00 am

  Soldier Field, 1410 Special Olympics Dr, Chicago

  
  
• Chi Town Show Down at Movement Wrigleyville 9:00 am

  Movement Wrigleyville, 1115 W Addison St, Chicago

  
  
• Sox Crawl Halfway to St. Paddy's Day 9:00 am

  Rate Field, 333 W 35th St, Chicago

  
  
• 31st Annual Retro on Roscoe Fest 9:00 am

  2000 W Roscoe St, Chicago

  
  
• Magnificent Mile™ Art Festival 10:00 am

  875 N Michigan Ave, Chicago, IL 60611

  
  
• 6th Annual World Dumpling Fest 11:00 am

  , 2555 N. Ashland Ave., Chicago 60614

  
  
• 2nd Annual Old Town Oktoberfest Returns to Wells 11:00 am

  1360 N Wells St, Chicago

  
  
• Hispanic Heritage with Jewel-Osco - Narragansett Ave, Chicago 12:00 pm

  Jewel-Osco, 2520 N Narragansett Ave, Chicago

  
  
• Mariano’s Brings the Flavors of Italy to Chicago with Grazie! 2026 12:00 pm

  1800 W Lawrence Ave, Chicago

  
  
• Games for Good Benefiting The Friendship Center 2:00 pm

  Begyle Brewing, 1800 W Cuyler Ave, Chicago

  
  
• Shubukai 50th Anniversary Celebratory Performance 3:00 pm

  The Edge Theater, 5451 N Broadway, Chicago

  
  
• The Jury Experience – The Deadly Boat Ride: Will Chicago Deliver Justice? 3:30 pm

  Museum Of Contemporary Art Chicago, 220 E Chicago Ave, Chicago

  
  
• Chicago's Theatre of Magic at the Palmer House a Hilton Hotel 4:30 pm

  Palmer House a Hilton Hotel, 17 E Monroe St, Chicago