Events and Things to Do in Chicago, IL

Thursday, October 8

Featured

Free Bra Fittings to Support Breast Cancer Awareness

OCT

8

10:00 AM

Macy's, 1 Woodfield Mall, Schaumburg, 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

8

10:00 AM

Macy's, 4909 Old Orchard Ctr, Skokie, 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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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...

Share

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...

Share

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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Tuesday, October 6

• See Chicago Dance 2026 BOLD IMPACT Gala 9:00 pm

  Venue West, 221 N Paulina St, Chicago

  
  

Wednesday, October 7

• Teen Exploration Day: Archery 4:00 pm

  Chicago

  
  
• Chicago Art Fair 5:00 pm

  THE MART, 222 W Merchandise Mart Plaza, Chicago

  
  
• 2026 Networking Extravaganza 5:30 pm

  1825 W Webster Ave, Chicago

  
  
• Lebanese Wine Dinner at Eden 6:00 pm

  2734 W Roscoe St, Chicago

  
  
• Spanish Tapas & Paella Dinner at Hyatt Lodge 6:00 pm

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

  
  

Thursday, October 8

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

  Macy's, 1 Woodfield Mall, Schaumburg

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

  Macy's, 4909 Old Orchard Ctr, Skokie

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

  McCormick Place, North Building, Level 3 – Hall B1

  
  
• Micheal O’Siadhail – Poetry Reading with Q&A 11:00 am

  American Writers Museum, 180 North N Michigan Ave, Chicago

  
  
• Chicago Art Fair 11:00 am

  THE MART, 222 W Merchandise Mart Plaza, Chicago

  
  
• SPIRITS & SPIRITS: A Spooky and Comedic Cocktail Experience 7:00 pm

  Waukesha Civic Theatre, 264 W Main St, Waukesha

  
  
• Faculty Recital: Sarah Kim, violin & Eugenia Jeong, piano 7:00 pm

  1020 W Sheridan Rd, Chicago

  
  
• Rhett Miller with Reilly Downes & the Acid Cowboys 7:30 pm

  City Winery Chicago, 1200 W Randolph St, Chicago

  
  
• 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