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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3.43

Chicago Night River and Lake Cruise

$46-$50

2 providers combined

Glide along the Chicago River at night

All taxes, fees and handling charges

3.18

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

2.98

Chicago Lake Michigan Skyline Cruise

From $33

2 providers combined

Marvel at Chicago's iconic skyline

Pet-friendly

2.85

Chicago Architectural River Cruise 90 Min

From $50

1 provider live

Admire Chicago's iconic skyline

Complimentary non-alcoholic beverages

2.73

Chicago Lake Michigan Dinner Cruise

$63-$342

3 providers combined

Dine on a gourmet 3-course meal

3-course plated dinner or lunch

2.49

Chicago Lake Michigan Sunset Cruise

$45-$65

3 providers combined

Enjoy the sun setting behind the Chicago skyline

All fees and taxes

2.44

Chicago River Architecture Cruise 90 Min

$44-$45

2 providers combined

Explore Chicago's iconic architecture

1.5-hour cruise

1.88

Chicago Lake Michigan Dinner Cruise

$105-$245

6 providers combined

Savor a gourmet buffet with diverse options

Unlimited coffee, hot tea, and iced tea