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FROM MONROE HARBOR - DOWNTOWN CHICAGO

Wedding & Bach Party Cruise

3 or 4 Hour Cruise

USCG Captain 

 Up to 10 Guests

FRI • SAT • SUN
LIMITED AVAILABILITY - SEE CALENDAR

Get the group together for the best wedding party ever! This 3 or 4 hour cruise will take you & your guests on a favorable sail from Monroe Harbor down the gorgeous coastline of Chicago's lakeshore. Want to party at the playpen or lay low & anchor in a private area? The choice is yours. Float on.

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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.

THE PERFECT EXPERIENCE ON LAKE MICHIGAN
TO CELEBRATE THEIR BIG DAY!

3 or 4 Hours

USCG Captain 
Up to 10 Guests

Our 37' luxury sailboat is the perfect venue for your celebration. We will depart from Monroe Harbor and curate a route to your desired location. This is a day of sailing & swimming Lake Michigan curated just for you and your guests. Make sure to take lots of photos!

Starting at $899

FRI • SAT • SUN
LIMITED AVAILABILITY

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Plan your Wedding Party 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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