Chicago Cruises & Sailing Tours - Page 4

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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4.4

Chicago Skyline Party Cruise on Lake Michigan

From $35

1 provider live

Sail in style on a Tiki Chic cruise

Enclosed Climate Controlled Space

4.37

Chicago River Architectural Lunch Cruise

From $74

1 provider live

Savor a plated lunch on the Chicago River

Unlimited coffee, hot tea, iced tea and water

4.33

Chicago Architecture Boat Tour with Drinks

From $42

1 provider live

Explore Chicago from a boat

Boat tour

4.17

Chicago River Architecture Cruise

From $57

1 provider live

Explore Chicago's iconic architecture

Local guide (docents)

4.13

Chicago Fireworks Dinner Cruise on Lake Michigan

$142-$273

3 providers combined

Marvel at Navy Pier's fireworks display

Plated dinner

4.13

Chicago Fireworks Dinner Cruise

From $116

1 provider live

Savor a chef-prepared buffet

Unlimited coffee, hot tea, iced tea, and water

4.07

Chicago River Brunch Cruise

$74-$94

2 providers combined

Savor a chef-prepared brunch

Narrated tour with ambient music

3.98

Chicago Driving Tour with River Cruise

$150-$254

2 providers combined

Cruise along the Chicago River

Admission to Shoreline Architecture Cruise

3.93

Chicago River Architecture Sunset Cocktail Tour

From $69

1 provider live

Cruise with a cocktail in hand

Chicago River Boat Architecture Tour

3.77

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

3.69

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

3.47

Chicago Architecture River Cruise

From $39

2 providers combined

Cruise along all branches of the Chicago River

Architecture river cruise