Luxury Sailing Yacht Charters Chicago, Illinois
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!


Licensed Captain Bob Swedlow and his first mate Lauren Swedlow have been in the charter business here in Chicago for the last decade. This father and daughter team have almost a half century of sailing experience between them.
Sailing in Chicago ´╗┐is our passion. After years of sailing for other charter companies, we now have a boat of our own. On board 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.


Live in the lap of luxury... if only for a couple of days.
Think of it as an exotic alternative to the usual hotel.
Think of it as the 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 master cabin has a full sized bed, fine linens, over 6 feet of headroom and is fully ventilated and air conditioned. Two bathrooms are available on board as well as a full galley. Breakfast is provided as well as an evening or morning sail.

Map & Directions

3600 N Recreation Drive, Chicago, Illinois 60613

Points of Interest
Luxury Sailing Yacht Charters
3600 N Recreation Drive, Chicago, Illinois

Typical Day

Chicago summers are second to none and there is no better way to enjoy the sun and fun without overheating. Sea breezes will cool you and the gentle motion will relax you on board our luxury sailing yacht.
Watching the Navy Pier Fireworks from a sailboat is amazing!
Spectacular fireworks go off twice weekly all summer long.
Memorial Day weekend through Labor Day!
Depart Belmont Harbor around 7:30pm with your group and sail off into the sunset as the skyline fades from day to night. Enjoy gorgeous skyline views while being served your favorite food and beverages.

Age range, type of group

People of all ages and all abilities are welcome and encouraged to come sailing with us. The best group size is 6 or less.
Great for marriage proposals, birthdays, anniversaries, team outings, and more.



Listing # RA-1285078

Starting at:
USD $200 per trip
Reservations & Information
for Luxury Sailing Yacht Charters
Email this advertiser to make your reservations or get more information.

Travel Dates

Add Your Free ListingAdvertise Your Travel Services

Add a multi-page listing promoting your accommodations, tours or travel services to customers on our network of travel sites. Your listing page can have up to 26 images, unlimited text, interactive map, availability calendar, ecards, photo-gallery and more.     » View Details
Disclaimer: Information provided through RealAdventures website, newsletters, emails or other services has been provided directly by the companies and/or individuals owning or offering the products/services. RealAdventures does not guarantee or warranty the accuracy of the information contained herein. It is the sole responsibility of the user to ensure the accuracy and clarity of any posted material and to determine the suitability of any service for their particular needs or requirements. Likewise, it is the responsibility of advertisers to determine the suitability and credit worthiness of potential customers prior to any transaction.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.