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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4.3

Chicago Fireworks Dinner Cruise on Lake Michigan

$142-$273

3 providers combined

Marvel at Navy Pier's fireworks display

Plated dinner

4.23

Chicago Skyline Party Cruise on Lake Michigan

From $35

1 provider live

Sail in style on a Tiki Chic cruise

Enclosed Climate Controlled Space

4.22

Chicago River Fireworks Tiki Bar Cruise 90 min

From $50

1 provider live

Cruise along the scenic Chicago River

Air-conditioned vehicle

4.2

Chicago River Architecture Cruise

From $57

1 provider live

Explore Chicago's iconic architecture

Local guide (docents)

3.98

Chicago River Brunch Cruise

$74-$94

2 providers combined

Savor a chef-prepared brunch

Narrated tour with ambient music

3.82

Chicago Night River and Lake Cruise

$46-$50

2 providers combined

Glide along the Chicago River at night

All taxes, fees and handling charges

3.79

Chicago Fireworks Dinner Cruise

From $116

1 provider live

Savor a chef-prepared buffet

Unlimited coffee, hot tea, iced tea, and water

3.67

Chicago River Architecture Sunset Cocktail Tour

From $69

1 provider live

Cruise with a cocktail in hand

Chicago River Boat Architecture Tour

3.65

Chicago Driving Tour with River Cruise

$150-$254

2 providers combined

Cruise along the Chicago River

Admission to Shoreline Architecture Cruise

3.63

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

3.59

Chicago Fireworks 3D Cruise

From $52

2 providers combined

Admire Navy Pier fireworks with music

All taxes, fees and handling charges

3.32

Chicago Lake Michigan Dinner Cruise

$63-$342

3 providers combined

Dine on a gourmet 3-course meal

3-course plated dinner or lunch