Chicago Cruises & Sailing Tours - Page 3

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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4.53

Chicago Thanksgiving Lunch Cruise on the River

From $16814

1 provider live

Savor a gourmet 3-course Thanksgiving meal

2-hour Thanksgiving lunch cruise on the Chicago River

4.53

Chicago Fireworks Cruise on Tall Ship Windy

From $114

1 provider live

Witness Chicago's skyline illuminated

Boarding ticket for public tour

4.52

Chicago Dinner Cruise on Lake Michigan

From $130

1 provider live

Savor a delicious dinner buffet

Delicious dinner buffet with freshly prepared entrees, salads, and desserts

4.51

Chicago Brunch Cruise on Lake Michigan

From $94

1 provider live

Savor a chef-prepared buffet

Unlimited coffee, hot tea, iced tea, and water

4.51

Chicago Fireworks Dinner Cruise

From $134

1 provider live

Savor a gourmet plated dinner

Best views of Navy Pier’s fireworks display (weather permitting)

4.51

Chicago Skyline Mimosa and Bloody Mary Cruise

From $50

1 provider live

Kick off your Sunday with mimosas

Lake Michigan Cruise

4.5

Chicago Boat Tour

From $299

1 provider live

Sail along the Chicago River

Admission fee

4.5

Chicago River Mimosa and Bloody Mary Cruise 1.5 hr

$41-$50

2 providers combined

Sip refreshing mimosas and Bloody Marys

River cruise

4.45

Chicago Skyline Sail on Tall Ship Windy

From $91

1 provider live

Sail on Chicago's official tall ship

Restroom on board

4.43

Chicago Tiki Bar Cruise on the River

From $41

1 provider live

Feel the warmth of a tiki-inspired design

Music

4.42

Chicago Fireworks Dinner Cruise on Lake Michigan

$142-$273

3 providers combined

Marvel at Navy Pier's fireworks display

Plated dinner

4.37

Chicago Seadog Fireworks Speedboat Cruise

From $62

2 providers combined

Marvel at Chicago's skyline during a thrilling speedboat ride

Scenic views of the Chicago skyline