Chicago Cruises & Sailing Tours - Page 4

46 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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3.87

Chicago Architecture River Cruise

From $39

2 providers combined

Cruise along all branches of the Chicago River

Architecture river cruise

3.79

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

3.23

Chicago Architectural River Cruise 90 Min

From $50

1 provider live

Admire Chicago's iconic skyline

Complimentary non-alcoholic beverages

3.16

Chicago Lake Michigan Brunch Cruise

$63-$176

2 providers combined

Feast on a freshly-prepared brunch buffet

Delicious brunch buffet with entrees, salads, and desserts

3.03

Chicago Fireworks 3D Cruise

From $52

2 providers combined

Admire Navy Pier fireworks with music

All taxes, fees and handling charges

2.95

Chicago Lake Michigan Dinner Cruise

$63-$342

3 providers combined

Dine on a gourmet 3-course meal

3-course plated dinner or lunch

2.91

Chicago Lake Michigan Sunset Cruise

$45-$65

3 providers combined

Enjoy the sun setting behind the Chicago skyline

All fees and taxes

2.79

Chicago Night River and Lake Cruise

$46-$50

2 providers combined

Glide along the Chicago River at night

All taxes, fees and handling charges

2.52

Chicago Lake Michigan Skyline Cruise

From $33

2 providers combined

Marvel at Chicago's iconic skyline

Pet-friendly

1.72

Chicago Lake Michigan Dinner Cruise

$105-$245

6 providers combined

Savor a gourmet buffet with diverse options

Unlimited coffee, hot tea, and iced tea