Chicago Cruises & Sailing Tours - Page 3

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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4.51

Chicago Skyline Mimosa and Bloody Mary Cruise

From $50

1 provider live

Kick off your Sunday with mimosas

Lake Michigan Cruise

4.51

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

4.49

Chicago Driving Tour with River Cruise

$150-$254

2 providers combined

Cruise along the Chicago River

Admission to Shoreline Architecture Cruise

4.48

Chicago Tiki Bar Cruise on the River

From $41

1 provider live

Feel the warmth of a tiki-inspired design

Music

4.45

Chicago Fireworks Dinner Cruise on Lake Michigan

$142-$273

3 providers combined

Marvel at Navy Pier's fireworks display

Plated dinner

4.44

Chicago River Fireworks Tiki Bar Cruise 90 min

From $50

1 provider live

Cruise along the scenic Chicago River

Air-conditioned vehicle

4.43

Chicago Skyline Party Cruise on Lake Michigan

From $35

1 provider live

Sail in style on a Tiki Chic cruise

Enclosed Climate Controlled Space

4.29

Chicago Architecture Boat Tour with Drinks

From $42

1 provider live

Explore Chicago from a boat

Boat tour

4.28

Chicago River Architecture Cruise

From $57

1 provider live

Explore Chicago's iconic architecture

Local guide (docents)

4.21

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

4.16

Chicago Fireworks Dinner Cruise

From $116

1 provider live

Savor a chef-prepared buffet

Unlimited coffee, hot tea, iced tea, and water

4.11

Chicago River Brunch Cruise

$74-$94

2 providers combined

Savor a chef-prepared brunch

Narrated tour with ambient music