Events and Things to Do in Chicago, IL

Saturday, May 30

Featured

North Center Community Yard Sale

MAY

30

10:00 AM

North Center-Roscoe Village, IL

Come shop unique finds and household treasures at the North Center Community Yard Sale, hosted by the North Center Neighbors...

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Featured

North Shore Artisan Market - Winnetka (This Sat-Sun, May 30-31)

MAY

30

10:00 AM

754 Elm St, Winnetka, IL

Join us in downtown Winnetka, IL this Sat-Sun, May 30-31 (10am-4pm both days). The North Shore Artisan Market will be OUTDOORS...

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Featured

$25 Day!

MAY

30

11:00 AM

Central Street, Central St, Evanston, IL

May has five Saturdays, and on Saturday, May 30, Central Street is declaring it $25 Day! Come spend $25 and show your support...

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Sunday, May 31

Featured

North Shore Artisan Market - Winnetka (This Sat-Sun, May 30-31)

MAY

31

10:00 AM

754 Elm St, Winnetka, IL

Join us in downtown Winnetka, IL this Sat-Sun, May 30-31 (10am-4pm both days). The North Shore Artisan Market will be OUTDOORS...

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Featured

North Center Community Yard Sale

MAY

31

10:00 AM

North Center-Roscoe Village, IL

Come explore the treasures at the North Center Community Yard Sale! This 2 day neighborhood event, hosted by the North Center...

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Featured

Out of the Darkness Campus Walk - Northwestern University

MAY

31

12:00 PM

Chicago, IL

HOPE WALKS HERE!!! Out of the Darkness Campus Walk Northwestern University Sunday, May 31, 2026 Schedule Check in: 12:00...

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Sunday, June 7

Featured

The Great Bake Walk

JUN

7

9:45 AM

Chicago, IL

THE GREAT BAKE WALK Follow The Crumbs To Something Sweet Sunday, June 7, 2026 - 10:00 AM - 1:00 PM Ticketholder Check-In:...

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Friday, June 12

Featured

Wrestling Interstellar 2, Live Professional Wrestling

JUN

12

6:00 PM

Juliana Restaurant, 3001 W Peterson Ave, Chicago, IL

Experience the high-octane energy of live Chicago pro wrestling at this family-friendly event presented by Ultimate Combat...

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Thursday, May 28

• Stygian Bough 8:00 pm

  Reggies Chicago, 2105 S State St, Chicago

  
  

Friday, May 29

• Fifth Annual Windy City Hot Dog Fest & Eating Contest 9:00 am

  4000 N Milwaukee Ave, Chicago

  
  
• 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: Tribute to Taylor Swift 6:30 pm

  Stan Mansion, 2408 N Kedzie Blvd, Chicago

  
  
• Raising a Glass to Women-Led Business Brands with Jen Wall of Barefoot Wine 6:30 pm

  Mariano's, 3030 N Broadway, Chicago

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

  Arts Center, 200 N Oak Park Ave, Oak Park

  
  
• Chicago Arte Agave Tequila & Mezcal Festival 7:00 pm

  Artifact Events, 4325 N Ravenswood Ave, Chicago

  
  
• Chicago Arte Agave Tequila & Mezcal Festival 7:00 pm

  Artifact Events, 4325 N Ravenswood Ave, Chicago

  
  
• Jagged Little Pill at The Lodge Performing Arts Center, Elgin 7:00 pm

  The Lodge Performing Arts Center, 18 Villa Ct, Elgin

  
  
• Now Extended Through June 21st: “Going Bacharach” Presenting the Greatest Hits of Bacharach at the A 7:30 pm

  Apollo Theater Chicago, 2550 N Lincoln Ave, Chicago

  
  
• Emo Night Brooklyn 8:00 pm

  Bottom Lounge, 1375 W Lake St, Chicago

  
  
• Come See Sinners on Friday, May 29, 2026, At Rooftop Cinema Club 8:15 pm

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

  
  
• Candlelight Oak Park: Tribute to Coldplay on Strings 8:45 pm

  Arts Center, 200 N Oak Park Ave, Oak Park

  
  
• Candlelight Oak Park: Tribute to Coldplay on Strings 8:45 pm

  Arts Center, 200 N Oak Park Ave, Oak Park

  
  
• Pete & Bas Save America 10:00 pm

  Subterranean, 2011 W North Ave, Chicago

  
  
• Come See 50 First Dates on Friday, May 29, 2026, At Rooftop Cinema Club 11:30 pm

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

  
  

Saturday, May 30

• Bubble Run | Chicago 2026 8:00 am

  SeatGeek Stadium, 7000 S Harlem Ave, Bridgeview

  
  
• Dino Dash 9:00 am

  Brookfield Zoo Chicago, 8400 31st St, Brookfield