Top Chicago Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

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Chicago Architecture River Cruise

5 star rating: Highly Recommended 2378 Reviews

Experience one of the world’s most beautiful cities on a 75-minute cruise on the historic Chicago River. On this architecture cruise, head down the main branch ... 

Location: Chicago, Illinois
Duration: 75 minutes

From USD $43.68

Chicago Architectural River Cruise

5 star rating: Highly Recommended 129 Reviews

Take in the views on this 90-minute Architectural Tour, a jaw-dropping excursion through a city that defied all expectations … even the laws of gravity.

Location: Chicago, Illinois
Duration: 90 minutes

From USD $48.16

Chicago Odyssey Dinner Cruise

4.5 star rating: Recommended 41 Reviews

Expect the exceptional on this 2.5-3 hour premier Chicago dinner cruise experience. Newly renovated, this luxury vessel features a newly furnished rooftop ... 

Location: Chicago, Illinois
Duration: 2.5 to 3 hours

From USD $88.26

Spirit of Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 77 Reviews

Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan. Glimpse top Chicago attractions like ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $108.66

Chicago City Tour with Optional Architecture River Cruise

5 star rating: Highly Recommended 91 Reviews

Don’t miss Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $35.00

Chicago Odyssey Lunch Cruise

4.5 star rating: Recommended 16 Reviews

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Tantalize your taste buds and discover Chicago's wonderful city skyline on this 2-hour lunch ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $74.66

Chicago Odyssey Brunch Cruise

5 star rating: Highly Recommended 8 Reviews

Experience Chicago's amazing skyline views from a unique vantage point on board this unforgettable 2 hour brunch cruise. With unsurpassed views of the Sears ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $95.06

Chicago Odyssey Valentine's Day Dinner Cruise

Your most memorable Valentine’s Day yet is waiting on the water, when you and your sweetheart join us aboard the Odyssey for dinner. Take a romantic 3 hour ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $149.46

Lake Michigan Sightseeing Cruise

4.5 star rating: Recommended 84 Reviews

Admire all of Chicago's fabulous lakefront sights and attractions on this 40-minute Lake Michigan boat tour. Cruise along Lake Michigan and take in amazing ... 

Location: Chicago, Illinois
Duration: 40 minutes

From USD $25.76

Spirit of Chicago Lunch Cruise with Buffet

With the sunshine reflecting off the lakefront, there’s no better place to enjoy an afternoon in Chicago than aboard a Spirit lunch cruise. Departing from ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $74.66

Private Morning Sail on Lake Michigan

Enjoy a private two-hour sailing charter for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $389.76

Private Chicago Sunset Sail on Lake Michigan

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $389.76

Private Day Sailing Excursion on Lake Michigan

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $389.76

Private Navy Pier Fireworks Sail in Chicago

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront.  Kick back, relax, and let the US Coast Guard licensed ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $445.76

Lake Michigan Speedboat Ride

4.5 star rating: Recommended 28 Reviews

Feel the need for speed? This exhilarating speedboat ride takes you out onto Lake Michigan for the ride of a lifetime. Experience the roar ... 

Location: Chicago, Illinois
Duration: 30 minutes

From USD $32.14
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