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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
59% OFF

BEST PRICE
Neon Paddle (up to 20% off)
AUG 7 - AUG 28
$125
15% OFF

BEST PRICE
Laugh Factory (Up to 30% off)
AUG 7 - SEP 30
$30
44% OFF
Private Cycleboat Lakefront Cruises
AUG 8 - OCT 1
$1.4K
15% OFF

BEST PRICE
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
AUG 9 - SEP 28

EXCLUSIVE
Millennium Park Summer Film Series (2025)
AUG 12 - AUG 19
Wine Wednesday Rooftop Movie Night - Chicago
AUG 13 - AUG 27

EXCLUSIVE
Air & Water Show Party - Hotel Lincoln
AUG 16 - AUG 17

EXCLUSIVE
Summer Time CHI Booze Cruises
AUG 16 - AUG 31
$30
26% OFF

BEST PRICE
Wrigley Rooftops - Chicago Cubs Season 2025 (Up to 15% off!)
AUG 17 - SEP 28
$93
12% OFF

BEST PRICE
Summer Yacht Series: Meet Me at the Playpen
AUG 23 - SEP 19
$80
59% OFF

BEST PRICE
Neon Paddle (up to 20% off)
AUG 7 - AUG 28
$125
15% OFF

BEST PRICE
Laugh Factory (Up to 30% off)
AUG 7 - SEP 30
$30
44% OFF
Private Cycleboat Lakefront Cruises
AUG 8 - OCT 1
$1.4K
15% OFF

BEST PRICE
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
AUG 9 - SEP 28

EXCLUSIVE
Millennium Park Summer Film Series (2025)
AUG 12 - AUG 19
Wine Wednesday Rooftop Movie Night - Chicago
AUG 13 - AUG 27

EXCLUSIVE
Air & Water Show Party - Hotel Lincoln
AUG 16 - AUG 17

EXCLUSIVE
Summer Time CHI Booze Cruises
AUG 16 - AUG 31
$30
26% OFF

BEST PRICE
Wrigley Rooftops - Chicago Cubs Season 2025 (Up to 15% off!)
AUG 17 - SEP 28
$93
12% OFF

BEST PRICE
Summer Yacht Series: Meet Me at the Playpen
AUG 23 - SEP 19
$80
59% OFF

BEST PRICE
Neon Paddle (up to 20% off)
AUG 7 - AUG 28
$125
15% OFF

BEST PRICE
Laugh Factory (Up to 30% off)
AUG 7 - SEP 30
$30
44% OFF
Private Cycleboat Lakefront Cruises
AUG 8 - OCT 1
$1.4K
15% OFF

BEST PRICE
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
AUG 9 - SEP 28

EXCLUSIVE
Millennium Park Summer Film Series (2025)
AUG 12 - AUG 19
Wine Wednesday Rooftop Movie Night - Chicago
AUG 13 - AUG 27

EXCLUSIVE
Air & Water Show Party - Hotel Lincoln
AUG 16 - AUG 17

EXCLUSIVE
Summer Time CHI Booze Cruises
AUG 16 - AUG 31
$30
26% OFF

BEST PRICE
Wrigley Rooftops - Chicago Cubs Season 2025 (Up to 15% off!)
AUG 17 - SEP 28
$93
12% OFF

BEST PRICE
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