Chicago Sailboat Charter with Captain 3 hr - Image 1

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Chicago Sailboat Charter with Captain 3 hr

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Rated on 1 provider · Why

Chicago
Updated October 31, 2026

Sail Chicago's lakefront with a private 3-hour charter, complete with captain, snacks, and stunning skyline views. Perfect for up to 12 guests.

About this tour

Experience the ultimate sailing adventure with a private sailboat charter from Navy Pier in Chicago. This exclusive 3-hour journey offers breathtaking views of the city's skyline and iconic landmarks such as the Chicago Lighthouse. With a USCG-Certified Captain at the helm, enjoy a personalized experience for up to 12 guests. Feel the wind in your hair as you take the helm, jump into the lake, or simply relax on deck. Complimentary beverages and snacks are provided, or you can bring your own to enjoy with the onboard surround sound Bluetooth speakers. Whether you're anchoring for a swim or soaking up the sun, this Chicago sailboat charter promises an unforgettable day on the water. Book now for a unique and memorable adventure.

Highlights

Sail along the Chicago Lakefront
Enjoy a private experience for up to 12 guests
Take the helm or relax on deck
Sip complimentary beverages and snacks
Listen to music with Bluetooth speakers

What's included

Included

USCG-Certified Captain trained in First Aid and CPR
Private use of a fully-permitted, fully-insured sailing yacht
Complimentary ice, beverages, and snacks
Fully stocked kitchenware, fridge, and bathroom
Stereo surround sound speakers with Bluetooth
Swim platform with ladder, life-jackets, noodles, and towels

Not included

Catering and drink packages available for added fee
Gratuity for captain at 10-20% is appreciated

Ratings on each provider

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What reviewers mention

Themes that come up most in this tour's reviews.

Often praised

Common complaints

Unpleasant boat odor

Important information

No high-heeled shoes, red wine, or glass objects
Unaccompanied minors not allowed
Not suitable for people with mobility impairments
People prone to seasickness should take precautions

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.

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The result is shown from 0 to 10. Tours without a usable provider rating are not scored.