Chicago Sailing Charters

NEW Chicago, IL 1 - 13 People 6 Hours From $3,000 Trip #14086
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

About Your Trip

Type

Boat Cruise, Booze Cruise, Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Set sail from downtown Chicago with Captain Charles for a private sailing experience aboard a spacious 47.7' Beneteau sailboat. Whether you're looking to spend the afternoon relaxing at the Playpen, celebrate with friends, or take in the skyline after sunset, these trips are built around your group and the kind of day you want to have.

Daytime trips run between 11 AM and 5 PM, with two trips available each day. For an evening experience,...

About Your Trip

Set sail from downtown Chicago with Captain Charles for a private sailing experience aboard a spacious 47.7' Beneteau sailboat. Whether you're looking to spend the afternoon relaxing at the Playpen, celebrate with friends, or take in the skyline after sunset, these trips are built around your group and the kind of day you want to have.

Daytime trips run between 11 AM and 5 PM, with two trips available each day. For an evening experience, trips are available from 7 PM to 11 PM, giving you a chance to watch Chicago light up from Lake Michigan.

For the daytime Playpen experience, you'll depart from the heart of downtown Chicago and cruise out toward one of the city's most popular summertime gathering spots. Once anchored up, settle in and enjoy the boat, the views, and plenty of time to swim and relax. Water toys and floats are available for the group, while a powerful Fusion stereo system with speakers and subwoofers throughout the boat keeps your favorite music playing.

Captain Charles and his team put a major emphasis on hospitality. Depending on your trip arrangements, they can put together a spread with fruit, sandwiches, High Noons, Modelos, tequila, rum, and more. The goal is to tailor the experience to your group rather than make everyone follow the same itinerary.

Your 47.7' Beneteau offers plenty of room to spread out and enjoy the trip. The spacious cockpit is ideal for hanging out with your group, while the interior features a large salon, comfortable cabins, and a well-equipped galley. The boat combines the performance of a true sailing yacht with the comfort and amenities you want for a private Chicago charter.

Evening trips offer a different side of the city. Cruise Lake Michigan as the sun goes down, relax with friends, celebrate a special occasion, or simply enjoy the Chicago skyline from a completely different perspective. These charters are a great fit for anniversaries, proposals, birthdays, group celebrations, corporate outings, or an evening away from the crowds.

Captain Charles holds a United States Coast Guard 100-ton Merchant Mariner Credential and has built his trips around attentive, personalized service. He works to make each charter feel like your own, whether that means a lively afternoon at the Playpen or a laid-back evening sail past the skyline.

Come aboard, settle in, and experience Chicago from Lake Michigan with Captain Charles handling the details.
Amenities

Type

Boat Cruise, Booze Cruise, Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Boat Restroom

This boat has a restroom.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

6 hours
1 Person
$3,000.00
2 People
$3,000.00
3 People
$3,000.00
4 People
$3,000.00
5 People
$3,000.00
6 People
$3,000.00
7 People
$3,000.00
8 People
$3,000.00
9 People
$3,000.00
10 People
$3,000.00
11 People
$3,000.00
12 People
$3,000.00
13 People
$3,000.00
Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Charles W.

Independent Guide
Captain Charles is a USCG 100-ton licensed captain offering private sailing charters from downtown Chicago. From Playpen afternoons to sunset cruises and celebrations, he tailors each trip around his guests with an emphasis on comfort, hospitality, and personalized service.

About Your Guide

Charles W.

Independent Guide
Captain Charles is a USCG 100-ton licensed captain offering private sailing charters from downtown Chicago. From Playpen afternoons to sunset cruises and celebrations, he tailors each trip around his guests with an emphasis on comfort, hospitality, and personalized service.
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Start Location & Lodging Options

Chicago, Illinois

About Your Boat

Boat photo for Chicago Sailing Charters
1/5
Boat Type
Yacht
Boat Manufacturer
Beneteau
Boat Length
47'
Boat Restroom
Yes

About Your Boat

Boat Type
Yacht
Boat Manufacturer
Beneteau
Boat Length
47'
Boat Restroom
Yes
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Trip Details & Amenities

Type

Boat Cruise, Booze Cruise, Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Boat Restroom

This boat has a restroom.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 14 days before the trip and receive credit back to your account. Cancelling within 14 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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