Chicago Cruises & Sailing Tours - Page 2

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.

Sort by:

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

4.57

Chicago Skyline Sail

From $88

1 provider live

Sail aboard a majestic tall ship

A great sailing adventure aboard a tall ship

4.57

Chicago Happy Hour Cruise

From $58

1 provider live

Feel the breeze off Lake Michigan

2-hour cruise on the Fred A. Busse

4.57

Chicago Private Catamaran Sailing

From $1500

1 provider live

Sail Chicago's largest chartered catamaran

Sailing from Monroe Harbor on a 38' luxury catamaran

4.57

Chicago Lake Michigan Dinner Cruise

From $176

1 provider live

Indulge in a chef-prepared dinner

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

4.57

Chicago Fireworks Cruise on a Historic Fireboat

From $63

1 provider live

Feel the thrill of Navy Pier’s fireworks

90-minute cruise on a historic fireboat

4.57

Chicago River Brunch Cruise

From $164

1 provider live

Savor a delicious plated brunch

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

4.55

Chicago Air and Water Show Cruise or Skydeck Experience

From $154

1 provider live

Experience the Air and Water Show from prime locations

Fast-track boarding/admission

4.54

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

4.53

Chicago River Architecture Cruise & Center Combo

From $71

1 provider live

Explore diverse architecture along the Chicago River

Architecture cruise on the Chicago River