1. Charter a  40ft Endurance Sailboat for 6 People in Chicago, Illinois
  2. Charter a  40ft Endurance Sailboat for 6 People in Chicago, Illinois
  3. Charter a  40ft Endurance Sailboat for 6 People in Chicago, Illinois

Charter a 40ft Endurance Sailboat for 6 People in Chicago, Illinois

2 reviews
4 bookings

Looking for a fun and unique way to experience Chicago Illinois? Grab some friends and hit the water with this beautiful a 40' Cruising Monohull for up to 6 people. Rates as low as $200 per hour (minimum of 3 hours). Other rates available below: Rates: • Private Charters on Weekdays (Monday-Friday) per hour (minimum of 3 hours): $200 • Private Charters on Wednesday Fireworks per hour (minimum of 3 hours): $225 • Private Charters on Weekend & Holidays per hour (minimum of 3 hours): $225 • Special Events (4th of July, Air, and Water show) per hour (minimum of 3 hours): $300 • Weekday Bed and Breakfast Morning Sail (2 hours): $700 • Wednesday Bed and Breakfast Fireworks Sail (3 hours): $900 • Saturday Bed and Breakfast Fireworks Sail (3 hours): $1,000 What You Can Expect: Onboard you will experience luxury, comfort, excitement, and relaxation as we go all out to cater to your needs while showing you the most incredible side of Chicago. Sail away from it all without leaving the city. Relax and enjoy a luxurious, private sailing trip on Lake Michigan. Bask in the sun and listen to the wind and the water while enjoying the gorgeous Chicago skyline. World class sailing and service await you onboard L’Argo, our classic comfort cruiser. The perfect choice for an unforgettable excursion. You can enjoy the ambiance, the comfort, the romance of staying "on the water" with all the amenities of a modern hotel. Live in the lap of luxury…if only for a couple of days. Think of it as your boat that you always wanted to own. Or just think of it as the most relaxing and romantic place to spend the night in Chicago during the summer. The cabins are fully ventilated and air-conditioned and feature memory foam mattresses, fine linens, private bathrooms, over 6’ of headroom and a skylight. Navy Pier is the destination for spectacular fireworks perfectly synchronized to music on Lake Michigan. Shows go off twice weekly all summer long. Memorial Day weekend through Labor Day! Depart Belmont Harbor around 8:00 pm with your group and sail off into the sunset as the skyline fades from day to night. What to Expect Onboard: Our "L'Argo" is a 40ft Endurance Sailboat with an inboard engine and takes up to 6 people comfortably. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
6 guests
Cruising Monohull


Meet our Team. Our licensed captain and his experienced crew have been in the charter business here in Chicago for the last decade.


2 reviews

5.0 out of 5!

  • Listing Accuracy

  • Departure & Return

  • Vessel & Equipment

  • Communication

  • Value

  • Itinerary & Experience

  1. SB

    The team was accommodating, kind, prompt, clean, and professional. I highly recommend taking a trip with this company

  2. JZ

Features & Details

  • Life jackets/required safety gear
  • Galley Stove & Oven
  • Air Conditioning
  • Watersports Equipment
  • Cabin
  • Wheel steering
  • Bimini
  • Inboard Engine
  • Autopilot
  • CD Player
  • Chart Plotter
  • Dinghy
  • Dodger
  • Single Engine
  • Fuel type: Diesel
  • Inverter
  • Berth
  • Furling Headsail
  • Furling Mainsail
  • Head

Approximate Location

You’ll get directions for the exact departure location when you make a booking inquiry.

The boat's approximate location on a map

Cancellation Policy

25% refund up to 3 days prior.

Additional Terms & Information

• We have a three (3) day cancellation policy. If you cancel outside of three (3) calendar days of your reservation the deposit will be refunded less a service fee. We wish we could just sail for fun all the time but our business partners mean business. Thank you for understanding. • Our rescheduling policy is very simple: If you reschedule within seven (7) calendar days of your reservation there is a $100.00 rescheduling fee. If you reschedule outside of seven (7) days of your reservation date and there may be a $50.00 rescheduling fee. • Weather and “Captains Call” Weather is part of the sailing experience – both the good and bad days. We must respect Mother Nature and we will not put anyone in danger. The Captain makes the final determination whether or not to sail. Swell Sailing has no liability or responsibility for delays, cancellations or failure to furnish services when caused by Acts of God, inclement weather, rough seas, storm warnings, lightning, thunderstorms, heavy fog, very strong winds, government orders, labor disputes, legal prohibitions, third-party interference's, or any other causes beyond the control of our Captains or the company/ When possible cancelled charters will be rescheduled. If this cannot be done due to time or other constraints, any deposits will carry over to the following year or we will provide a full refund. • The Captain may exercise good judgment and discretion to cancel any charter without refund for any of the following reasons: passengers over-intoxicated, unconsciousness, aggravation of previous injury, illegal drug use, unruly or reckless behavior, perceived risk or threat to the operation of the boat or to others, criminal act or violation of local law and boating regulations, or behavior that distracts the Captain or Crew from their duties.

Similar Listings

Top destinations nearby

Real reviews from happy GetMyBoaters.

19,150+ reviews

4.9 out of 5!