Chicago Cruises & Sailing Tours - Page 2

46 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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4.57

Chicago River Plated Dinner Cruise

From $208

1 provider live

Savor a delicious plated dinner

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

4.57

Chicago Sailboat Charter with Captain 3 hr

From $719

1 provider live

Sail along the Chicago Lakefront

USCG-Certified Captain trained in First Aid and CPR

4.57

Chicago River Dinner Cruise

From $204

1 provider live

Savor a delicious plated dinner

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

4.56

Chicago River Architecture Cruise 90 Min

$44-$45

2 providers combined

Explore Chicago's iconic architecture

1.5-hour cruise

4.56

Chicago Fireworks Sailboat Charter

From $567

1 provider live

Sail along Chicago's stunning lakefront

Use of Bluetooth speakers

4.55

Chicago Brunch Cruise on Lake Michigan

From $137

1 provider live

Savor a delicious brunch buffet

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

4.54

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

4.53

Chicago Brunch Cruise on Lake Michigan

From $94

1 provider live

Savor a chef-prepared buffet

Unlimited coffee, hot tea, iced tea, and water

4.53

Chicago Fireworks Dinner Cruise

From $134

1 provider live

Savor a gourmet plated dinner

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

4.52

Chicago River Architecture Cruise & Center Combo

From $71

1 provider live

Explore diverse architecture along the Chicago River

Architecture cruise on the Chicago River

4.52

Chicago Boat Tour

From $299

1 provider live

Sail along the Chicago River

Admission fee

4.52

Chicago Fireworks Cruise on Tall Ship Windy

From $114

1 provider live

Witness Chicago's skyline illuminated

Boarding ticket for public tour