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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Friday, June 5

Featured

American Dreams

JUN

5

7:30 PM

Niles North High School, 9800 Lawler Ave, Skokie, IL

Northshore Concert Band presents American Dreams: A Program Inspired by the Enduring Ideals of the American Dream: Liberty,...

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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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Friday, May 29

• 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

• North Shore Artisan Market - Winnetka (This Sat-Sun, May 30-31) 10:00 am

  754 Elm St, Winnetka

  
  
• North Center Community Yard Sale 10:00 am

  North Center Neighborhood, Chicago

  
  
• $25 Day! 11:00 am

  Central Street, Central St, Evanston

  
  
• 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

  
  
• The Magnificent Mile™ Spring Art Fest 10:00 am

  875 N Michigan Ave, Chicago

  
  
• Wrigleyville Taco Crawl | 7 Tacos Included | Chicago's Taco Party! 11:00 am

  Wrigleyville's Best Bars & Restaurants (Full List in Details), 3518 N. Clark St., Chicago, IL 60657

  
  
• Come See Lilo & Stitch (2002) on Saturday, May 30, 2026, At Rooftop Cinema Club 11:00 am

  The Emily Hotel, 311 N Morgan St, Chicago

  
  
• Stan's Donuts Grand Opening at Mariano's Aurora 12:00 pm

  Mariano's, 3025 E New York St, Aurora

  
  
• Fifth Annual Windy City Hot Dog Fest & Eating Contest 12:00 pm

  4000 N Milwaukee Ave, Chicago

  
  
• Fire Up the Grill at Mariano's Bucktown! 12:00 pm

  Mariano's, 2112 N Ashland Ave, Chicago

  
  
• Come See 13 Going on 30 on Saturday, May 30, 2026, At Rooftop Cinema Club 1:15 pm

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

  
  
• Chicago Dance Month Kickoff Celebration 3:00 pm

  Navy Pier Lake Stage

  
  
• Come See Brown Sugar on Saturday, May 30, 2026, At Rooftop Cinema Club 4:15 pm

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