Events and Things to Do in Winnetka-Glencoe, IL

Saturday, May 2

Featured

We Do Estate Sales full house of treasures Highwood Sale

MAY

2

9:30 AM

281 Michigan Ave, Highwood, IL

Come shop with us Sat-May 2, 930-3, and Sunday May 3, 10-3. we’ve got a full house! 281 Michigan Ave , Highwood. Vintage pool...

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Featured

The International Gem & Jewelry Show - Rosemont, IL (May 2026)

MAY

2

10:00 AM

Donald E. Stephens Convention Center, 5555 N River Rd, Rosemont, IL

The International Gem & Jewelry Show Returns To The Donald E. Stephens Convention Center! Shop Directly From Wholesalers &...

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Sunday, May 3

Featured

Chicago Artisan Market in Fulton Market - Sun, May 3rd (Spring Market)

MAY

3

11:00 AM

401 N Morgan St, Chicago, IL

Join us this Sun, May 3rd (11am-5pm) to shop small, local & sustainable with 115+ talented artisans at our flagship Chicago...

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Saturday, May 9

Featured

NWA at StudioONE

MAY

9

6:30 PM

StudioOne Events LLC, 1799 Green Bay Rd, Highland Park, IL

Get ready for a night of high-flying, hard-hitting LIVE Pro Wrestling as NWA Chicago returns to StudioONE in Highland Park on...

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Thursday, May 21

Featured

Lake Forest College Community Engagement Lifelong Learning Series: Film Discussion Course

MAY

21

5:30 PM

Lake Forest College, 555 N Sheridan Rd, Lake Forest, IL

Explore the art of cinema through the lens of legendary directors John Ford and Akira Kurosawa—join Lake Forest College...

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Saturday, May 2

• First Presbyterian Rummage Sale 8:00 am

  700 N Sheridan Rd, Lake Forest

  
  
• We Do Estate Sales full house of treasures Highwood Sale 9:30 am

  281 Michigan Ave, Highwood

  
  
• The International Gem & Jewelry Show - Rosemont, IL (May 2026) 10:00 am

  Donald E. Stephens Convention Center, 5555 N River Rd, Rosemont

  
  
• Growing Together: Saturday Storytime with Ruth Spiro 10:30 am

  The Book Stall, 811 Elm St, Winnetka

  
  

Sunday, May 3

• Chicago Artisan Market in Fulton Market - Sun, May 3rd (Spring Market) 11:00 am

  401 N Morgan St, Chicago

  
  
• Author Talk 2:00 pm

  1774 2nd St, Highland Park

  
  
• Schmidt-Burnham Log House Opening Day 2:00 pm

  1140 Willow Rd, Winnetka

  
  

Tuesday, May 5

• Trevian SC 2026-27 Season Girls Tryouts 4:30 pm

  North Shore Sportscenter, 1900 Old Willow Rd, Northbrook

  
  

Saturday, May 9

• NWA at StudioONE 6:30 pm

  StudioOne Events LLC, 1799 Green Bay Rd, Highland Park

  
  
• Saturday Storytime with Jonathan Stutzman & Jay Fleck: Uh-Oh, Hugo! 10:30 am

  The Book Stall, 811 Elm St, Winnetka

  
  

Sunday, May 10

• Schmidt-Burnham Log House Open to Public 2:00 pm

  1140 Willow Rd, Winnetka

  
  

Tuesday, May 12

• Chicago Homes: An Evening with Carla Bruni at The Book Stall 6:00 pm

  The Book Stall, 811 Elm St, Winnetka

  
  
• Show & Tell: Work in Progress 7:00 pm

  Writers Theatre, 325 Tudor Ct, Glencoe

  
  
• Evaluating the Pretrial Reforms in Illinois SAFE-T Act 7:00 pm

  Winnetka Public Library (Lloyd Room),768 Oak Street, Winnetka

  
  

Thursday, May 14

• Turning Pages: An Evening with Roberta Rubin 6:00 pm

  The Book Stall, 811 Elm St, Winnetka

  
  

Friday, May 15

• Rembrandt Chamber Musicians: Glinka Sextet with Marta Aznavoorian 7:00 pm

  Nichols Concert Hall, 1490 Chicago Ave, Evanston

  
  
• Wilmette Community Band Spring Concert 7:30 pm

  Community House Winnetka, 620 Lincoln Ave, Winnetka

  
  

Sunday, May 17

• Schmidt-Burnham Log House Open to Public 2:00 pm

  1140 Willow Rd, Winnetka

  
  

Tuesday, May 19

• The Calamity Club: An Evening with Kathryn Stockett 7:00 pm

  The Skokie School, 520 Glendale Ave, Winnetka

  
  

Thursday, May 21

• Lake Forest College Community Engagement Lifelong Learning Series: Film Discussion Course 5:30 pm

  Lake Forest College, 555 N Sheridan Rd, Lake Forest