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STARTING AT $799 - INCLUDES 6 GUESTS

Skyline Sunset Cruise

2 Hour Cruise

USCG Captain 

 Up to 10 Guests

FRIDAY • SUNDAY
DEPARTING 6:30PM

Relax and enjoy a captained sunset cruise on our sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off from Monroe Harbor in downtown Chicago and set sail to a favorable course on Lake Michigan. Bring your own food and drinks, listen to your favorite music, and take in the views of our city’s iconic skyline while the sun is setting.

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OVER 500 PRIVATE CHARTERS IN CHICAGO SINCE 2018

ONE BOAT. ONE CAPTAIN. ONE UNIQUE EXPERIENCE.

Guests:

Up to 10

Length:

37'

Bluetooth

Speakers

Private
Bathroom

Refrigerator
Access

Kitchenware
Available

S/V Dragonfly offers world-class sailing with comfortable amenities, encouraging you & your guests to focus on the adventurous day ahead.

The bimini umbrella in the cockpit gives ample shade and some light rain protection in our main seating area. Willing guests are welcome to relieve our captain and try their hand at the helm!

Lounging space for sunbathing and lake-gazing is available on the foredeck. This will be a popular locale for photo opportunities on beautiful days! Those camera rolls are no match for these views.

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foredeck

Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and comfortable salon seating area. The perfect place to store your bags, keep your drinks cool and prepare the days provisions.

400+ FIVE STAR REVIEWS

7 years of fresh waters, exclusive parties & unforgettable experiences.

2 Hours

USCG Captain 
Up to 10 Guests

Our private Skyline Sunset Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique experience of seeing the city from the water at sunset. If you're looking for the perfect happy hour in Chicago - this is the cruise for you.

Starting at $799

FRIDAY • SUNDAY
DEPARTING 6:30PM

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Plan your Skyline Sunset Cruise now!

flexible booking plan

Flexible Booking Plan - 50% Deposit, Fully-Refundable

We recognize that plans change, so we've designed our booking options to be incredibly flexible. This ensures you have the freedom to make adjustments with ease, providing peace of mind for your experience with On A Boat Sailing.

100% Refund up to Two Weeks From Departure

50% Refund up to 48 Hours From Departure

Full Refund for Weather Related Cancellations

Swap Dates With No Fees-Subject to Availability

chicago sailboat cruise


STEP ABOARD
Be first for private sailing offers & special event happenings on Chicago's famous Lakefront. 

Welcome to the crew!

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