Chicago Cruises & Sailing Tours

12 experiences to discover

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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4.41

Chicago Architecture River Cruise and Guided Tour

From $254

Explore Chicago's skyline from the river

All attraction admission fees

4.34

Chicago Lake Michigan Fireworks Dinner Cruise

$103-$122

Savor a multi-course buffet dinner

Three-hour cruise

4.31

Chicago River Brunch Cruise

$103-$110

Savor a chef-prepared brunch

2-hour cruise

4.26

Chicago Lake Michigan Dinner Cruise with Fireworks

$163-$171

Savor a gourmet 3-course dinner

Unlimited coffee, hot tea, iced tea, and water

3.53

Chicago Night River & Lake Cruise

From $45

Glide along the Chicago River and Lakefront

All taxes, fees and handling charges

3.44

Chicago Nighttime River and Lake Cruise

$40-$45

Experience Chicago's skyline as a glittering jewel

1.5-hour nighttime boat cruise of Chicago River and Lake Michigan

3.36

Chicago Fireworks Cruise with 3D Glasses

From $52

Admire fireworks with 3D glasses

2-hour cruise

3.22

Chicago Lake Michigan Brunch Cruise

$105-$108

Feast on a freshly-prepared buffet

Delicious brunch buffet with entrees, salads, and desserts

3.06

Chicago Lake Michigan Sunset Cruise

$34-$45

Admire the sunset over Chicago's skyline

1.5-hour sunset cruise

2.67

Chicago Lake Michigan Skyline Cruise

From $33

Marvel at Chicago's iconic skyline

Pet-friendly

2.57

Chicago Lake Michigan Lunch Cruise

$66-$77

Dine on a gourmet buffet or plated meal

Unlimited coffee, hot tea, iced tea, and water

1.92

Chicago Lake Michigan Thanksgiving Lunch Cruise

$108-$120

Dine on a gourmet Thanksgiving lunch

2-hour Thanksgiving lunch cruise on Lake Michigan