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Chicago Sailboat Rentals

Whether you're cruising the city skyline, partying hard at the playpen or taking in the Navy Pier fireworks from the best seats in the house - you won't forget the time you sailed Lake Michigan in luxury & style!

Wednesdays • Fridays • Saturdays • Sundays




We are a one boat, one captain, small family business sharing our passion for sailing. It's our mission to deliver the best possible experience to you and your crew.

Captain Greg & First Mate Cait

We have a combined 25 years sailing experience allowing us to curate the best possible experience for our guests-it's easy because we love what we do. Expect expert boat handling, top-notch service and unforgettable vibes.


Up to 10







  • 👥 How many guests are allowed in our party?
    Our standard Skyline, Fireworks and Playpen bookings reserves the entire boat for up to 6 guests.
  • ⚡️What if there is bad weather the day of our charter?
    We do our best to communicate with you expectations of poor weather ahead of your sail. We will sail in the rain and advise guests dress accordingly or request to reschedule/rain check if available. If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure. If your charter is cancelled we will contact you and offer either to delay, reschedule or return a full refund. Please be advised Chicago weather is unpredictable and the Lake has its own weather. It is often very difficult to predict the conditions on the Lake as they can be very different compared to the city and surrounding suburbs of Chicago.
  • 👨‍👩‍👧‍👦 Can we bring our kids?
    We love having kids onboard, but please be advised of the risks of boating and the range of conditions from smooth sailing to very rough and choppy. We have a recommended age minimum of 5 years old. Children under 12 will be encouraged to wear a life jacket at all times. It is 100% the parent's responsibility to monitor children and ensure that they stay within designated safe areas of the boat. Being a sailboat, conditions will be unstable at times.
  • 🐶 Can I bring my pet?
    With so many animals prone to seasickness and unbalance due to motion of the boat, we do not encourage bringing pets on board without prior boating experience. If you do wish to bring a cat or small to medium sized dog we encourage you to bring a pet life jacket. We do not provide pet life jackets. Of course a parrot on the shoulder is always welcome on the high seas, arrrr matey!
  • 🤢 Will I get sea sick?
    Lake Michigan is subject to a wide range of conditions from calm to rough seas depending on the weather which will cause the boat to be unbalanced at times. As such some passengers may experience seasickness. Please see below for our tips to prevent seasickness: • Be well rested and do not drink alcohol excessively the night before • Take antiemetic drugs (Dramamine) the night before to get it in your system and again 30 minutes before the cruise • Be sure to have plain foods ahead of the cruise. An empty stomach or foods that do not sit well (greasy, spicy, dairy etc.) are not good ideas • Wear an acupressure wristband such as sea-band
  • 📸 Do you host special events like proposals, bachelorette parties, photo shoots etc?
    Yes of course! We have had many fun and memorable events on the boat. We are happy to discuss the details ahead of time for what you have in mind. We provide catering, provisioning and or decorations for an added fee.
  • 🚻 Is there a bathroom on board?
    Yes, although on a boat we call it a head 😉
  • 👨‍✈️ Is a Captain included?
    Yes Captain is included and inclusive of the price shown. Gratuity for the captain is much appreciated!
  • 🍾What food and drink can I bring on the boat?
    We provide basic non-alcoholic drinks and light packaged snacks onboard. You may bring any beverages of your choosing including beer, wine, champagne, or hard seltzers. No hard liquor on the boat please per our own safety precautions. Please do not bring red wine or other items that may stain the boat if spilled. We provide glassware for our guests. We have a fridge onboard to keep things cool, along with utensils, glasses and dish-ware.
  • 🕶 What else should our group bring?
    If its a hot day and you want to swim, bring a bathing suit and towel! We have a few spare towels onboard the guests may share. Other good things to bring include sunglasses, hat, light rain-jacket and layers. Temperatures and wind on the Lake will ALWAYS be cooler than on land. We humbly request no dark rubber soled shoes as they can scuff up the boat. We provide lifejackets, pool floats, blankets, sunscreen, bug spray, and full first-aid.
  • 👟 What type of shoes should I wear?
    Boat shoes are great but not a requirement. We humbly ask for no black soled shoes or high heels as these can scuff or scratch the boat. Guests are welcome to remove shoes and go barefoot while on the boat if desired.
  • 🍤 Can you provide catering or provisioning for our group?
    Yes, we customize a fee for catering and provisioning pending on the size of the group and order. Generally the fee starts at $199 plus cost of goods.
  • 👗 Is there a dress code for the boat?
    No dress code for our yacht club! We want guests to be comfortable and come as they are. We recommend casual athletic wear that is quick drying and no denim. Please be advised the Lake is always cooler than the city by about 10 degrees so bring layers if sailing with us in the Spring or Fall months.
  • 🍻 What do I need to know further about BYOB/Alcohol?
    Guests are allowed to bring alcohol in the form of beer, wine and hard seltzer drinks. We have a no hard liquor policy while on the boat for our guests safety. We do not provide or sell alcohol on board unless arranged through our catering or provisioning service. All beer must be in cans, not glass. Wine bottles are acceptable. We have wine openers and plastic wine glasses on board. We provide use of our fridge for keeping drinks cool and usually do have ice available. If ice is desired let us know ahead of time to ensure we have some on board before you arrive.
  • 📍Where do we get on the boat?
    Google "Monroe Harbor Public Dock", or see map below. This dock runs north/south, is concrete and has wood pilings. Please plan ahead to arrive on time as we cannot guarantee adjustments to our return time based on our future schedule. Downtown Chicago often has many events going on in the summer, so be advised of road closures and traffic. The closest drop off point is the cul-de-sac at 400 E. Monroe St. and from there it is a 2-minute walk north of the Chicago Yacht Club along the Lakefront Trail to get to the dock. Look for our boat Dragonfly no earlier than 15 minutes prior to departure as this is a pickup dock only and not our permanent slip.
  • 🚙 Is there parking at the harbor?
    The closest parking is the underground Millennium Lakeside Garage- price is $20-$35 depending on the day and special events in the area. The entrance ramp is off of Columbus Dr. between Monroe St. and Randolph St. Look for signs for the Lakeside entrance gates when you get to the bottom of the ramp. 1. Once through the ticket gate, drive straight forward until you see a ramp down to level 2, stop. 2. Turn right, in front of the ramp, drive forward all the way until you reach a concrete wall, 3. Turn left, drive forward all the way, you should see a group of parked cars, boat trailers and pedestrian doors in the corner, the columns will say section 117. Park here. 4. Go through the pedestrian doors, walk down the ramp. On your left there will be glass doors. 5. Walk up the stairs to the crosswalk on Lake Shore Drive. 6. See map below for the directions to the dock.

Jeanneau is a French luxury brand of cruising class yachts made for day cruises & entertaining. Our yacht offers comfort & extra seating compared to other sailboats. The bimini in the cockpit provides shade while the dodger provides a wind break from the cool breezes on the Lake. Lounging space in the sun is available on the foredeck. Down below, the teak interior cabin has two private changing rooms, a bathroom with shower, kitchen and salon seating area.

We sail out of
Monroe Harbor
in Downtown Chicago

On A Boat Sailing
dates & times:


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


3 Hours
Captain Included
Up to 10 Guests

Soak up the sights of our city’s iconic skyline! This 3-hour cruise will take you & your guests on a favorable sail from Monroe Harbor down the gorgeous coastline of Chicago's lakeshore, giving a unique perspective on the city's world-class architectural wonders. If you're looking for a private and intimate way to experience Chicago - this is the cruise for you.

Starting at $899
sunset fountain.jpg
4 Hours
Captain Included
Up to 10 Guests

Chicago's famous lakefront party is back. This 4-hour private charter is designed for you & your friends to party in luxury. We will depart from Monroe Harbor, anchoring the boat in the party zone. Whatever you do - don't forget a bathing suit, some sunscreen & something cold to sip on!

Starting at $1,099
2.5 Hours
Captain Included
Up to 10 Guests

This 2.5 hour sailboat cruise will take you & your group to the closest possible viewing area for the famous Navy Pier Fireworks show. We've all seen fireworks - you've never seen anything like this before.

Starting at $799
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

Start planning your summer sail now!

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