Chicago Cruises, Sailing & Water Tours

Chicago Cruises, Sailing & Water Tours

Cruises, Sailing & Water Tours

Only Show: Day Cruises | Dinner Cruises | Lunch Cruises | Night Cruises | Sailing Trips

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Chicago Architecture River Cruise

5 star rating: Highly Recommended 1284 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 ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes

From USD $33.60
$41.44 Save $7.84

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

4.5 star rating: Recommended 48 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 ...  Read more

Location: Chicago, Illinois
Duration: 6 hours

From USD $124.00

Chicago Architectural River Cruise

5 star rating: Highly Recommended 19 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 ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $42.56

Chicago Sunset Dinner Cruise with Buffet

4.5 star rating: Recommended 52 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 ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $104.58

Chicago Dinner Cruise

4.5 star rating: Recommended 36 Reviews

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

Location: Chicago, Illinois
Duration: 3 hours

From USD $129.06

Lake Michigan Sightseeing Cruise

4.5 star rating: Recommended 30 Reviews

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

Location: Chicago, Illinois
Duration: 40 minutes

From USD $19.60

Lake Michigan and Chicago River Architecture Cruise by Speedboat

4.5 star rating: Recommended 109 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! ...  Read more

Location: Chicago, Illinois
Duration: 75-minutes

From USD $39.38

Chicago Urban Adventure Cruise

4.5 star rating: Recommended 3 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 ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $34.00

Chicago 3D Fireworks Cruise on Lake Michigan

2.5 star rating: It was OK, but could have been better 3 Reviews

What's better than seeing Chicago's fireworks at night on the water? Seeing them in 3D. The 2-hour cruise includes a professional Captain and crew. Seeing ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $35.00

Chicago City Tour and Chicago River Cruise

4 star rating: Recommended 68 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 ...  Read more

Location: Chicago, Illinois
Duration: 4 hours

From USD $60.00

Chicago Brunch Cruise

5 star rating: Highly Recommended 4 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $92.34

Lake Michigan Speedboat Ride

4.5 star rating: Recommended 21 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 ...  Read more

Location: Chicago, Illinois
Duration: 30 minutes

From USD $25.46

Chicago Lunch Cruise

4.5 star rating: Recommended 10 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $74.66

Chicago by Night Cruise

5 star rating: Highly Recommended 1 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 ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $35.00

Americas Cup Sailing Racing Experience on Lake Michigan

Sail in beautiful Lake Michigan in between The Shedd Aquarium and Navy Pier, aboard the famous America’s Cupyachts: ‘Stars and Stripes’ and ‘Abracadabra.’  ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $150.00

Lakeside Architecture Sail

Join us for a 75 minute sail on Lake Michigan while we explore Chicago's architectural majesty.

Location: Chicago, Illinois
Duration: 75 minutes

From USD $35.40

Real Pirates of the Inland Seas Sail

Join us on a journey through time on Lake Michigan! On this sail 75-minute journey you will hear stories of piracy and much more.

Location: Chicago, Illinois
Duration: 75 minutes

From USD $35.40

Spirit Ships and Haunted Harbors of Chicago

Join us on this stirring and spooky storytelling adventure peers into the dark waters of Great Lakes ghost ships and the darker deeds of souls that sailed its ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes

From USD $35.40

A Sailor's Life for Me Chicago Cruise

What did it take to survive and thrive as a Tall Ship sailor? Find out on this 75 minute sail on the waters of Lake Michigan and take in the views of the ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes

From USD $35.40

Chicago Fireworks Sail

A Special Event Sail! Relax and enjoy Navy Pier’s spectacular fireworks display from the best seat in town. Then, get your history fix with a rousing ...  Read more

Location: Chicago, Illinois
Duration: 75 minutes

From USD $40.71

Tall Ship Pub Sail

Join us on this 90-minute Pub Sail on Lake Michigan. Come relax with friends and enjoy the view!

Location: Chicago, Illinois
Duration: 75 minutes

From USD $57.82

Chicago Halloween Haunted Cruise

4 star rating: Recommended 2 Reviews

Add a new adventure to your Halloween festivities this year. Come join all the fun on a haunted one hour speedboat cruise on Lake Michigan. ...  Read more

Location: Chicago, Illinois
Duration: 60 minutes

From USD $37.06
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Only Show: Day Cruises | Dinner Cruises | Lunch Cruises | Night Cruises | Sailing Trips

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