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ON A BOAT SAILING - SUMMER 2024

Chicago Sailboat Rentals

USCG-Certified Captain 

37' Luxury Sailboat

Up to 10
Guests

Birthdays • Graduations • Photoshoots • Reunions • Bachelor(ette) Parties • Engagements • Wedding Groups • Summer Getaways • Romantic Moments

Any celebration is better from Lake Michigan!

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OVER 500 PRIVATE BOOKINGS SINCE 2018

CHICAGO SAILBOAT RENTALS 
ALL CHARTERS & CRUISES

Starting price includes up to 6 guests. Custom pricing for additional guests up to 10 during checkout.

Click '
book now'  button on any product below to browse dates, times, FAQs, and more. Our aim is to make the process from booking to sailing as seamless as possible. Reach out if you have any questions!

3-Hour Experience

This 3-hour sailboat cruise will take you & your guests on a favorable sail down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural landscape. If you're looking for a private & intimate way to experience Chicago - this is the cruise for you.

Starting at $899

WED • FRI • SAT • SUN
10AM, 1:30PM & 5:30PM DAILY

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2-Hour Experience

Relax and enjoy a captained sunset cruise from our 37' luxury sailing yacht, Dragonfly. 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 as the sun sets before you. You won't believe the photos!

Starting at $799

FRI • SUN
6:30PM DAILY

Chicago's famous lakefront party is back. This 4-hour chicago sailboat charter is designed for you & your friends to party in luxury - where ever you choose! We will depart from Monroe Harbor, sailing Chicago's lakeshore to begin your voyage. On nice days, you & your guests can drop anchor to swim & float anywhere on the Lakefront. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

Starting at $1,099

FRI • SAT • SUN
10AM & 2:30PM DAILY

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2.5 Hour Experience

This 2.5 hour Chicago sailboat rental will split your time with us between sailing Lake Michigan & watching the famous Fireworks show at Navy Pier. These are the best seats you can possible have for a world-class fireworks show. We've all seen fireworks - you've never seen anything like this before. Our guests say this is an unforgettable experience.

Starting at $899

7PM WEDNESDAY'S
8PM SATURDAY'S

WHAT MAKES ON A BOAT SAILING DIFFERENT

We're a one boat, one captain small family business sharing our passion for sailing with our customers. Our boat, S/V Dragonfly, has played host to thousands of guests since our first private sailing charter in 2018.

Unparalleled Sailing Expertise

Captain Greg Scannell and First Mate Cait Scannell share a combined 25 years of sailing experience, including an 8-month, 5,500 nautical mile voyage from Chicago to the Bahamas and back in 2021.

500+ private charters later, we're actively curating the best experiences for our guests looking to explore the joys of sailing on Lake Michigan. Let us show you!

Luxury & Comfort Aboard S/V Dragonfly

Our 37' sailing yacht was designed for entertaining & comfort. Guests love the flexibility of luxury sailing along with dropping anchor & swimming or floating with a cold one, should the weather permit.

Bluetooth connectivity to play your own music, onboard bathroom facilities, and ample space above and below deck makes stepping aboard Dragonfly for the day an absolute breeze.

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“I rented [Dragonfly] to celebrate my bday with 6 close girlfriends. Greg was very communicative before the trip. He answered all my questions in a very timely manner. The boat is very spacious!

Dyna, Chicago, IL

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