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October 22, 2026 · 1 min read

Things to Do in Chicago This Weekend: October 23–25, 2026

Chicago is packed with fun this weekend — from Halloween parades to glowing pumpkin displays. Here are three can't-miss events to check out!

1. Arts in the Dark Parade

Arts in the Dark Parade – illuminated costumes and puppets along Columbus Drive

Saturday, October 24 · Downtown Chicago

A free Halloween parade featuring elaborate costumes, illuminated puppets, music and performances along Columbus Drive.

Event details →

2. Night of 1,000 Jack-o'-Lanterns

Night of 1,000 Jack-o'-Lanterns at Chicago Botanic Garden

Through Sunday, October 25 · Glencoe

An incredible nighttime stroll through more than 1,000 glowing, intricately carved pumpkins at the Chicago Botanic Garden.

Tickets and details →

3. Jack's Pumpkin Pop-Up

Jack's Pumpkin Pop-Up – giant urban pumpkin patch in River West

All weekend · River West

A giant urban pumpkin patch with a corn maze, carnival games, axe throwing, food trucks and festive photo opportunities.

Event details →

However you spend it

However you spend your weekend, Chicago's got something magical in store. Happy Halloween season! 🎃🍂

Thinking about calling one of these neighborhoods home? Get in touch anytime — I'm always happy to talk neighborhoods, weekend plans, or both.

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Katerina Vielehr · Broker licensed in Illinois · @properties Christie's International Real Estate