Chicago Cruises & Sailing Tours - Page 5

56 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Chicago. Our unbiased ratings help you find the perfect experiences for your trip.

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3.02

Chicago Architecture Boat Tour with Drinks

From $42

1 provider live

Explore Chicago from a boat

Boat tour

2.96

Chicago River Mimosa and Bloody Mary Cruise 1.5 hr

$41-$50

2 providers combined

Sip refreshing mimosas and Bloody Marys

River cruise

2.77

Chicago Architecture River Cruise

From $39

2 providers combined

Cruise along all branches of the Chicago River

Architecture river cruise

2.76

Chicago Architectural River Cruise 90 Min

From $50

1 provider live

Admire Chicago's iconic skyline

Complimentary non-alcoholic beverages

2.43

Chicago River Ghost and Dark History Night Cruise

$46-$50

2 providers combined

Explore Chicago's eerie past on a night cruise

Live commentary on board

2.12

Chicago Lake Michigan Sunset Cruise

$45-$65

3 providers combined

Enjoy the sun setting behind the Chicago skyline

All fees and taxes

2.06

Chicago Lake Michigan Dinner Cruise

$105-$245

6 providers combined

Savor a gourmet buffet with diverse options

Unlimited coffee, hot tea, and iced tea

2.04

Chicago Lake Michigan Skyline Cruise

From $33

2 providers combined

Marvel at Chicago's iconic skyline

Pet-friendly