Events and Things to Do in Chicago, IL

Friday, October 9

Featured

Free Bra Fittings to Support Breast Cancer Awareness

OCT

9

10:00 AM

Macy's, 111 N State St, Chicago, 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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Featured

Free Bra Fittings to Support Breast Cancer Awareness

OCT

9

10:00 AM

Macy's, 1 Oakbrook Center, Oak Brook, 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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Sunday, October 11

Featured

IWRG vs GALLI: La Jaula de Las Locas — Chicago Showdown at Cicero Stadium, October 11 6pm

OCT

11

5:30 PM

Cicero Stadium, 1909 S Laramie Ave, Cicero, IL

Experience the high-octane thrills of Lucha Libre Internacional featuring an action-packed card headlined by a massive Jaula De...

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Thursday, October 15

Featured

Free Bra Fittings to Support Breast Cancer Awareness

OCT

15

10:00 AM

Macy's, 1 Hawthorn Ctr, Vernon Hills, IL

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

Share

Featured

Free Bra Fittings to Support Breast Cancer Awareness

OCT

15

10:00 AM

Bloomingdale's, 900 N Michigan Ave, Chicago, IL

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

Share

Friday, October 16

Featured

Camerata Chicago — Mendelssohn's 'A Midsummer Night's Dream'

OCT

16

7:30 PM

Fourth Presbyterian Church, 126 E Chestnut St, Chicago, IL

Camerata Chicago, led by the chamber orchestra's founder and music director Drostan Hall, opens its 23rd concert season with a...

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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, October 8

• Sketch Playlist 9:30 pm

  The iO Theater, 1501 N Kingsbury St, Chicago

  
  

Friday, October 9

• Free Bra Fittings to Support Breast Cancer Awareness 10:00 am

  Macy's, 111 N State St, Chicago

  
  
• Free Bra Fittings to Support Breast Cancer Awareness 10:00 am

  Macy's, 1 Oakbrook Center, Oak Brook

  
  
• St. Jude Heroes-Bank of America Chicago Marathon Expo 9:00 am

  McCormick Place, North Building, Level 3 – Hall B1

  
  
• Chicago Art Fair 11:00 am

  THE MART, 222 W Merchandise Mart Plaza, Chicago

  
  
• Marathon Meals at FireLake Grill House & Cocktail Bar 12:00 pm

  FireLake Grill House and Cocktail Bar, 221 N Columbus Dr, Chicago

  
  
• State and Lake Chicago Tavern Marathon Meals 12:00 pm

  State and Lake Chicago Tavern, 201 N State St, Chicago

  
  
• Beyond the Grid Fairmont Chicago’s Art Series 1:00 pm

  Fairmont Chicago, Millennium Park, 200 N Columbus Dr, Chicago

  
  
• Three-course marathon dinner at the Albert 4:00 pm

  the Albert, 228 E Ontario St, Chicago

  
  
• Nisi Greek Grill to Bring Flavors of The Greek Islands to Rosemont On October 9th 4:00 pm

  Nisi Greek Grill, 5509 Park Pl, Rosemont

  
  
• Carb Load Menu | Chicago Marathon 5:00 pm

  Somerset, 1112 N State St, Chicago

  
  
• 10th Annual Lincoln Park Wine Fest 5:00 pm

  1001 W Wrightwood Ave, Chicago

  
  
• Celebración de los Muertos: Papel Picado and Paint & Sip Workshops at The Rivvy 6:00 pm

  Hotel 55 Chicago Downtown, 55 E Ontario St, Chicago

  
  
• Martin Sexton - Live Wide Open Tour 2026 6:00 pm

  City Winery Chicago, 1200 W Randolph St, Chicago

  
  
• SPIRITS & SPIRITS: A Spooky and Comedic Cocktail Experience 6:00 pm

  Waukesha Civic Theatre, 264 W Main St, Waukesha

  
  
• The Sheraton Improv Social with The Second City 7:00 pm

  Sheraton Grand Chicago Riverwalk, 301 E North Water St, Chicago

  
  
• Loeffler's Rediscovered Octet 7:30 pm

  915 E 60th St, Chicago

  
  
• Chicago Vampire Ball 2026 8:00 pm

  Warwick Allerton - Chicago, 701 N Michigan Ave, Chicago

  
  
• Candlelight Oak Park: Tribute to Bad Bunny 8:45 pm

  Arts Center of Oak Park, 200 N Oak Park Ave, Chicago, Illinois 60302

  
  

Saturday, October 10

• St. Jude Heroes-Bank of America Chicago Marathon Expo 8:30 am

  McCormick Place, North Building, Level 3 – Hall B1