Charter 38ft "Jolly Mon" Sun Dancer Motor Yacht In Chicago, Illinois

Cuddy Cabin/Walk Around
38 ft
6 Guests

About This Boat

Experience a great day on the water in Chicago, Illinois by boat! Charter the 38 feet "Jolly Mon" Sea Ray Sun Dancer Motor Yacht for up to 6 people. Rate as low as $225 per hour (minimum of 3 hours). Fuel surcharge added at the end of charter.


Private Charter

• Weekday (Monday-Friday, 3 hours min): $225 per hour plus fuel
• Weekends (Saturday, Sunday & Holidays, 3 hours min): $250 per hour plus fuel


• Weekday (Monday-Friday, 3 hr min): $225 per hour
• Weekends (Saturday, Sunday & Holidays, 3 hr min): $250 per hour

Summer Event

• Weekday (Monday-Friday, 3 hr min): $200 per hour
• Weekends (Saturday, Sunday & Holidays, 3 hr min): $250 per hour
• July 4th Fireworks, Chicago Air & Water Show (4 hr min): $300 per hour


• Wednesday Night Fireworks (3.5 hours cruise): $225 per hour
• Saturday Night Fireworks (4 hours cruise): $250 per hour
• July 4th Fireworks (4-hour cruise): $300 per hour


• $350

What You Can Expect:

Enjoy the Wednesday and Saturday night Fireworks display at Navy Pier, explore the sites of the Chicago River or views of the Chicago Skyline from the Lake, or just relax and enjoy a day or evening out on Lake Michigan. Our certified captains and crew will take you cruising on a private charter along the beautiful waters of Lake Michigan providing you with extraordinary views of the Chicago skyline. Whether you prefer to cruise and bask in the sunshine or enjoy the evening views of Chicago’s beautiful lakefront, your sailing experience will be relaxing and memorable. Our fellow sailors often use our services for engagement proposals, special date ideas, birthday celebrations, romantic anniversaries and moonlight sails. Whatever your needs, charter our boat and we will make your experience memorable.

What To Expect Onboard:

"Jolly Mon" is a 38’ Sea Ray Sun Dancer, and ready to cruise Lake Michigan and the Chicago River. Be prepared to relax in the beautiful wraparound cockpit lounge. The seating area includes a removable table that easily converts to a sun pad. "Jolly Mon" is equipped with a sumptuous salon. Bring aboard the food and beverage of your choice, bottled water is always provided. Of course, an onboard bathroom will keep everyone comfortable on the water.

Entertain up to 6 passengers on a private charter to view the skyline from the lake or explore the sites of the Chicago River.


  • Type: Cuddy Cabin/Walk Around
  • Capacity: 6 People
  • Make Model: Sea Ray 38 SunDancer DA
  • Year: 2000
  • Rental Minimum: 3 hours
  • Length: 38 ft
  • Cancellation: Full Refund 7 Days Prior

Rental Requirements

Frequently Asked Questions

All charters have a three (3) hour minimum

All rates are based on a “group rate” of up to six people in your party. Rates include captain fees, crew fees, docking fees and taxes. Gratuity is not included and is at your discretion.

What is your cancellation policy?

We have a seven (7) day cancellation policy.Cancellation outside of seven (7) calendar days of your reservation will be refunded less a service fee. We wish we could just sail for fun all the time but our business partners mean business.

Is there a bathroom on board?

Yes, we actually have two bathrooms on board our vessels. We take pride in providing you with a VERY clean and safe sailing vessel.

Do you supply a cooler on board?

Yes we supply your party with two coolers, one for beverages and one for food. The beverage cooler will be stocked with ice.

What happens if the weather is bad?

We must respect Mother Nature and will not put anyone in danger. If it’s raining, lightning, hailing or just too rough to sail we will reschedule your group for a future date or provide a full refund. The weather in Chicago can change in a flash so we typically wait until the last minute to cancel a charter. We keep an eye on the NOAA Radar.

What should we bring along?

We recommend that you bring a jacket for evening sails. It’s also in your best interest to take a peek at the weather and dress accordingly. Offshore breezes can be cool at times. Don’t worry if you forget your jacket because we have a few extra on the boat. Sunscreen is always a good idea, but we do not allow oil or spray sunscreen on the boat. Don’t forget a camera. Click this link to check on the weather conditions in Chicago.

What about shoes?

Non marking shoes are allowed, or just take off your shoes while on board.

Can we bring our dog(s)?

We love our furry friends but more times than not we enjoy the sailing experience more than they do. We kindly ask you to refrain from bringing your pooches along.

What refreshments can we bring? Is alcohol permitted?

Feel free to bring any type of beverage and/or food that you like. Full sailors are happy sailors, so enjoy. We supply plates, glassware, flatware, napkins, wine opener, bottled water, and a cooler stocked with ice. If you need to purchase something nearby, Whole Foods is located on Halsted or Jewel on Broadway.

Are children allowed?

Yes, children love to sail, just let us know their ages/size so that we have the correct personal flotation devices available.

Will my cell phone work on the lake?

Most cell phones do work, it does depend on your service provider.

Can I drive the yacht?

Yes, you can be as hands on as you like once the captain is out of the harbor. Of course the captain is always in charge.

Do I have to help with sailing the boat or will someone be handling it all?

The captain will handle everything. If you are interested in learning to sail you can participate.

How far into Lake Michigan do you sail?

We usually sail along the lakefront as requested by our clients. The distance into the lake will depend upon the wind.


  • Wi-Fi
  • Life jackets/required safety gear
  • Cabin
  • Toilet
  • Wheel steering
  • Bimini
  • Cuddy Cabin
  • Licensing Required
  • Inboard Engine
  • Autopilot
  • CD Player
  • Chart Plotter
  • Climate Control
  • Dodger
  • Dual Comm-forward seating
  • Twin Engine
  • Fuel type: Diesel
  • Inverter
  • Galley Stove & Oven
  • Berth
  • Air Conditioning
  • Head

More Images

More Sea Ray 38 SunDancer DA images


Charter 38ft "Jolly Mon" Sun Dancer Motor Yacht In Chicago, Illinois
5 5 7
5.00 5

Our group has a terrific time on the boat and would absolutely recommend it. The boat was spacious, clean, easy to find, and provided a great experience!

August 2018
5.00 5

Had a fabulous day out on the lake! Definitely the highlight of our trip to Chicago!

August 2018
5.00 5

wonderful day, beautiful boat and the owners were so kind and accommodating. Will definitely book again!

August 2018
5.00 5

Good time

August 2017

Meet Captain Josef

Captain Josef

From Chicago

Member Since Sep 2015

Contact Owner
Email Address
Request to Book Captain Josef