Top Illinois Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

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Chicago Architecture River Cruise

5 star rating: Highly Recommended 2452 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 $41.44

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

4.5 star rating: Recommended 100 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 Architectural River Cruise

5 star rating: Highly Recommended 136 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

Lake Michigan and Chicago River Architecture Cruise by Speedboat

5 star rating: Highly Recommended 158 Reviews

The rumors are true! The best way to soak in all of Chicago's rich architectural beauty is by joining us on our 75-minute River and Lake Architectural Cruise. ... 

Location: Chicago, Illinois
Duration: 75 minutes

From USD $42.50

Spirit of Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 81 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 Architecture Fireworks Cruise

5 star rating: Highly Recommended 6 Reviews

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

Chicago City Minibus Tour with Optional Architecture River Cruise

5 star rating: Highly Recommended 95 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 $37.00

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

Architectural River Cruise and Chicago Helicopter Tour

Explore Chicago by air and water! See landmark buildings and architectural favorites up close as you cruise down the Chicago River.  Then, take off aboard a ... 

Location: Chicago, Illinois
Duration: 15 to 90 mins

From USD $178.00
$223.00 Save $45.00

Chicago Odyssey Dinner Cruise

4.5 star rating: Recommended 43 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: 3 hours

From USD $108.66

Chicago Odyssey Lunch Cruise

4.5 star rating: Recommended 19 Reviews

Welcome aboard Chicago's largest luxury yacht at Navy Pier! Satisfy your appetite and take in breathtaking views of Chicago's skyline on this 2-hour lunch ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $77.38

Chicago Urban Adventure Cruise

5 star rating: Highly Recommended 22 Reviews

This popular 1.5-hour daytime river and lake tour, the Urban Adventure Cruise, delights families of all ages with incredible views of Chicago's world-renowned ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $35.00

Chicago City Tour and Chicago River Cruise

4 star rating: Recommended 88 Reviews

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

Location: Chicago, Illinois
Duration: 4 hours

From USD $73.95

Lake Michigan Sightseeing Fireworks Cruise

5 star rating: Highly Recommended 1 Review

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

Chicago by Night Cruise

4.5 star rating: Recommended 8 Reviews

Glide along the Chicago River and lakefront as you're dazzled by the sparkle of the city at night on this 90-minute tour cruise. Includes a professional ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $36.00

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

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

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

Spirit of Chicago Lunch Cruise with Buffet

5 star rating: Highly Recommended 1 Review

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 Lakeside Architecture Tour

4 star rating: Recommended 8 Reviews

Leave the hustle and bustle behind, and enjoy a leisurely Skyline Sail aboard Chicago’s Official Tall Ship. Our crew today will be EXPLORING Chicago's ... 

Location: Chicago, Illinois
Duration: 75 minutes

From USD $33.60

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

Chicago Skyline Sightseeing Cruise

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular ... 

Location: Chicago, Illinois
Duration: 75 minutes

From USD $33.60

Chicago Odyssey Brunch Cruise

5 star rating: Highly Recommended 8 Reviews

There is no better way to see Chicago than from the waters of Lake Michigan. Enjoy the amazing skyline views on board during this unforgettable 2-hour brunch ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $99.14

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

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
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