Top Illinois Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

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Chicago Architecture River Cruise

5 star rating: Highly Recommended 2404 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

Viator VIP: Willis Tower Skydeck Early Access, Trolley City Tour and Chicago River Cruise

4.5 star rating: Recommended 99 Reviews

See classic Chicago sights with this Viator VIP package that includes early entry to the Skydeck in Willis (formerly Sears) Tower where you'll be greeted and ... 

Location: Chicago, Illinois
Duration: 6 hours

From USD $124.00

Chicago City Minibus Tour with Optional Architecture River Cruise

5 star rating: Highly Recommended 93 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

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 Architectural River Cruise

5 star rating: Highly Recommended 130 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 42 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 $101.86

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

Lake Michigan and Chicago River Architecture Cruise by Speedboat

5 star rating: Highly Recommended 154 Reviews

Chicago is renowned for its stunning and original architecture, and the most relaxing way to see it is on a cruise on the Chicago River! You'll learn all ... 

Location: Chicago, Illinois
Duration: 75-minutes

From USD $42.50

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 $77.38

Chicago Architecture Fireworks Cruise

On Wednesday and Saturday evenings in the summer, take a dramatic, 90-minute night-time cruise and get a glittering view of Chicago's iconic skyscrapers. Your ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $42.56

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

Chicago City Tour and Chicago River Cruise

4 star rating: Recommended 83 Reviews

Discover Chicago from both land and water on this scenic half-day tour. Take a narrated coach tour through the city’s South Side and see highlights including ... 

Location: Chicago, Illinois
Duration: 4 hours

From USD $73.95

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

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

Lake Michigan Sightseeing Fireworks Cruise

On Wednesday and Saturday evenings in the summer, admire all of Chicago's fabulous lakefront sights and attractions on this 60-minute Lake Michigan boat tour, ... 

Location: Chicago, Illinois
Duration: 60 minutes

From USD $31.36

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

Chicago Themed Evening Cruises

Set sail from Navy Pier on a special evening cruise, where each cruise allows guests to experience a different side of Chicago. Events range from wine tasting ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $54.88

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

Real Pirates of the Inland Seas Sail

5 star rating: Highly Recommended 1 Review

Join in on a journey through time on Lake Michigan. On this 75-minute sailing journey, you will hear stories of piracy and much more.

Location: Chicago, Illinois
Duration: 75 minutes

From USD $33.60

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

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 $99.14
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