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Published on APR 30, 2025
The Best Ways to Spend a Day on the Water in Chicago
Booze cruises, architecture tours, jet skiing and more. Here's how to spend a sunny day in Chicago's Playpen. ⛵☀️
By Chicago Bucket List
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Laugh Factory
SEP 10 - 30
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$20
14% OFF
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
SEP 12 - DEC 20
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EXCLUSIVE
Wrigley Rooftops - Chicago Cubs (Up to 15% Off!)
SEP 12 - 13
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Oktoberfest Nation - Chicago
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Chicago Stars FC Matches 2026 (Up to 20% off!)
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$24
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Nightmare on Clark Street
OCT 10 - NOV 1
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EXCLUSIVE
Halloween on the Pier at Offshore Rooftop
OCT 30 - 31
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EXCLUSIVE
The Christkindlmarket Wrigleyville at Gallagher Way
NOV 20 - DEC 31
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The Christkindlmarket Chicago at Daley Plaza
NOV 20 - DEC 24
EXCLUSIVE
The Christkindlmarket Aurora at RiverEdge Park
NOV 20 - DEC 24
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Laugh Factory
SEP 10 - 30
From
$20
14% OFF
Up, Up and Away Yoga on the 99th floor at Skydeck Chicago
SEP 12 - DEC 20
From
EXCLUSIVE
Wrigley Rooftops - Chicago Cubs (Up to 15% Off!)
SEP 12 - 13
From
BEST PRICE
Oktoberfest Nation - Chicago
SEP 17 - OCT 24
From
EXCLUSIVE
Chicago Stars FC Matches 2026 (Up to 20% off!)
SEP 20
From
$24
BEST PRICE
Nightmare on Clark Street
OCT 10 - NOV 1
From
EXCLUSIVE
Halloween on the Pier at Offshore Rooftop
OCT 30 - 31
From
EXCLUSIVE
The Christkindlmarket Wrigleyville at Gallagher Way
NOV 20 - DEC 31
EXCLUSIVE
The Christkindlmarket Chicago at Daley Plaza
NOV 20 - DEC 24
EXCLUSIVE
The Christkindlmarket Aurora at RiverEdge Park
NOV 20 - DEC 24
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