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Chicago Private Catamaran Sailing

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Rated on 1 provider · Why

Chicago
Updated October 31, 2026

Sail Chicago's skyline on a private catamaran. Enjoy luxury amenities and customizable adventures for up to 12 guests.

About this tour

Embark on a private catamaran sailing adventure in Chicago, setting sail from Monroe Harbor. This luxurious 38-foot vessel offers a unique way to experience the city's stunning skyline with up to 12 guests. Enjoy amenities like a full kitchen, barbecue grill, and floatie toys for a fun-filled day on the water. Whether you're celebrating a special occasion or seeking a relaxing escape, this customizable journey ensures unforgettable memories. Book now and sail into an extraordinary Chicago experience.

Highlights

Sail Chicago's largest chartered catamaran
Admire breathtaking skyline views
Relax with luxurious onboard amenities
Experience a tranquil sunset sail
Customize your sailing adventure

What's included

Included

Sailing from Monroe Harbor on a 38' luxury catamaran
Yacht Concierge service
Large Yeti cooler and refrigerator
Full kitchen with stove/oven
Bluetooth radio and barbecue grill
Floatie toys for water fun

Not included

Hire a qualified operator if not self-operating
Operator costs around $10 - $11 per person per hour
Gratuity for the operator not included

Ratings on each provider

The ratings and review counts each booking site shows for this tour.

GetYourGuide

Rating unavailable

View on GetYourGuide

Important information

Groups over 6 require a qualified operator
Not suitable for those prone to seasickness
Weight limit: 331 lbs (150 kg)
Not recommended for people over 95 years

How this score is calculated

This tour has no TourTruth score yet: GetYourGuide doesn't show a usable rating for it. It gets a score as soon as a provider lists one.

How the score works

Each provider rating is turned into a percentile: the share of that provider's ratings it beats, weighted by review counts.
Listings on different providers are combined in proportion to their review counts.
Tours with few reviews are pulled toward the average until more reviews come in, so a handful of perfect reviews can't top the list.
The result is shown from 0 to 10. Tours without a usable provider rating are not scored.