Fun Things to Do in Chicago
Chicago is a big city that runs on neighborhoods — friendly, unpretentious, and packed with summer festivals, lakefront life, and the best bar culture in the country. It is one of the easiest US cities to plug into.
Happening this week in Chicago
New plans in Chicago drop on Waypoint every week — hikes, trivia nights, dinners, and more. Join the app to see what's on near you and tap to come along.
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Lakefront Trail runs & rides
The 18-mile lakefront path is the city living room — run clubs and cycling groups meet here daily.
Best for: Showing up solo
Summer festivals & street fests
Chicago practically invented the neighborhood street fest — show up and the whole block is your social setting.
Best for: Weekend groups
Bar trivia & pub leagues
Trivia and bags (cornhole) leagues turn a bar night into an instant team.
Best for: Small groups
Beach volleyball at North Avenue
Lakefront beaches host pickup volleyball all summer — newcomers welcome.
Best for: Active people
Improv & comedy classes
Chicago is the home of improv — drop-in classes are a famously fast way to make friends.
Best for: First-time meetups
Where to go in Chicago
Wicker Park
Indie bars, record shops, and a buzzing nightlife strip
Logan Square
Craft cocktails, the 606 trail, and creative crowd
Lincoln Park
Lakefront, the zoo, and lively sports bars
Pilsen
Murals, taquerias, and a thriving arts scene
West Loop
Restaurant Row, galleries, and after-work spots