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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
Arab Summer Cruise (Up to 10% off!)
SEP 6
$75
4% OFF
Summer Yacht Series: Meet Me at the Playpen
SEP 19
$75
14% OFF
BEST PRICE
Wine Wednesday Rooftop Movie Night - Chicago
WEDNESDAY
EXCLUSIVE
Neon Paddle (up to 20% off)
AUG 27 - AUG 28
$125
15% OFF
BEST PRICE
Laugh Factory (Up to 30% off)
AUG 27 - SEP 30
$30
44% OFF
Private Cycleboat Lakefront Cruises
AUG 28 - OCT 1
$1.4K
15% OFF
BEST PRICE
Wrigley Rooftops - Chris Brown (Up to 15% Off!)
THURSDAY
$167
19% OFF
BEST PRICE
Summer Time CHI Booze Cruises
AUG 31
$30
26% OFF
BEST PRICE
Wrigley Rooftops - Chicago Cubs Season 2025 (Up to 15% off!)
SEP 1 - SEP 28
$93
BEST PRICE
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
SEP 6 - SEP 28
EXCLUSIVE
Arab Summer Cruise (Up to 10% off!)
SEP 6
$75
4% OFF
Summer Yacht Series: Meet Me at the Playpen
SEP 19
$75
14% OFF
BEST PRICE
Wine Wednesday Rooftop Movie Night - Chicago
WEDNESDAY
EXCLUSIVE
Neon Paddle (up to 20% off)
AUG 27 - AUG 28
$125
15% OFF
BEST PRICE
Laugh Factory (Up to 30% off)
AUG 27 - SEP 30
$30
44% OFF
Private Cycleboat Lakefront Cruises
AUG 28 - OCT 1
$1.4K
15% OFF
BEST PRICE
Wrigley Rooftops - Chris Brown (Up to 15% Off!)
THURSDAY
$167
19% OFF
BEST PRICE
Summer Time CHI Booze Cruises
AUG 31
$30
26% OFF
BEST PRICE
Wrigley Rooftops - Chicago Cubs Season 2025 (Up to 15% off!)
SEP 1 - SEP 28
$93
BEST PRICE
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
SEP 6 - SEP 28
EXCLUSIVE
Arab Summer Cruise (Up to 10% off!)
SEP 6
$75
4% OFF
Summer Yacht Series: Meet Me at the Playpen
SEP 19
$75
14% OFF
BEST PRICE
Wine Wednesday Rooftop Movie Night - Chicago
WEDNESDAY
EXCLUSIVE
Neon Paddle (up to 20% off)
AUG 27 - AUG 28
$125
15% OFF
BEST PRICE
Laugh Factory (Up to 30% off)
AUG 27 - SEP 30
$30
44% OFF
Private Cycleboat Lakefront Cruises
AUG 28 - OCT 1
$1.4K
15% OFF
BEST PRICE
Wrigley Rooftops - Chris Brown (Up to 15% Off!)
THURSDAY
$167
19% OFF
BEST PRICE
Summer Time CHI Booze Cruises
AUG 31
$30
26% OFF
BEST PRICE
Wrigley Rooftops - Chicago Cubs Season 2025 (Up to 15% off!)
SEP 1 - SEP 28
$93
BEST PRICE
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
SEP 6 - SEP 28
EXCLUSIVE
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