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Bucket Listers

attractions & tours, +1

Published JUL 17, 2025

The Best Weekend Getaways & Day Trips from Chicago

Swap skyscrapers for small-town charm, lakeside beaches, and lots of Wisconsin cheese at these getaway trips from Chicago. 🛣 🚘

By Chicago Bucket List

Recommended Experiences

Summer Yacht Series: Meet Me at the Playpen

AUG 23 - SEP 19 

$80

$33

59% OFF

BEST PRICE

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