Chicago's Best Boats and Yacht Charters

We have Two of the Best Private Charter Party Boats in Chicago

We offer two beautiful powerboats that can take a total of 25 people out together on Lake Michigan. A 51′ Searay Sundancer and a 35′ Searay Sundancer boat that can accommodate a lot of guests. We can bring both of our boats together so you and your entire group can do a “Tie-Up in the Playpen”. Summer in Chicago without spending time with all your friends in the Playpen should not be missed. Please book your group trips early before we get all booked up
Charters can range from going to the world-famous “Playpen” where we can anchor and crank up the sound system and go for a swim or chill on our rafts to cruising along the lakefront and by Navy Pier. You can also take a trip through the “Locks” and down the Chicago River or some blue water cruising past the Chicago Lighthouse, the cribs of Chicago, and into the deep blue waters of Lake Michigan and taking in some of the best views of Chicago
Chicago Sailboat and Yacht Charters provide our guests with exclusive, private charters that offer complete luxury, flexibility, and customization. Take your friends & family on a cruise and experience Chicago like you never thought was possible a priceless adventure.
On Wednesday & Saturday nights we offer Sunset & Fireworks cruises just off of Navy Pier.
Experience firsthand the relaxing beauty of a peaceful sail on our 4+ hour and all day Private boat Charter. Boating in Chicago is the perfect way to end the day with friends. Maximum of 12 guests on a boat.

Come enjoy the beauty of Chicago in the lap of luxury. Our Lake Michigan boat charters include many points of interest around Chicago such as: The Playpen, Navy Pier, Chicago River Locks, Chicago lighthouse, Adler Planetarium, Shedd Aquarium, Soldiers Field, Buckingham Fountain and many more.

Chicago Yacht Rentals - A Unique Way to Explore the City

On Wednesday & Saturday nights we offer Sunset & Fireworks cruises just off of Navy Pier.

Our cruises are perfect for these special occasions:

  • Bachelorette or Bachelor Parties
  • Anniversary Cruises
  • Special Occasions Cruises
  • Chicago Scene Boat Party
  • Birthday Parties
  • Corporate events
  • The World Famous “Playpen” we anchor, turn up the music, crack open the drinks and dive into the water
  • Chicago River Cruise – Hanging out at City Winery
  • Chicago Air & Water Show (Friday, Saturday & Sunday middle of August)
  • Holiday Weekends (Memorial Day, 4th of July, and Labor Day- Book early they book up fast)
  • Lollapalooza- Listening to the concert from Monroe Harbors
The owners Ted Widen, the owner of & Mark Kaplan started the world Famous Chicago Scene Boat party in the “Playpen” over 20 years ago. We know how to show people a great time in Chicago.
Our Boats: We offer two beautiful powerboats to choose from. We have a Searay Sundancer 51′ and a Searay Sundancer 35′ cruiser. Between both boats, we can take out a total of 25 guests and do a “Tie-Up in the Playpen” just off Lakeshore Drive. Please book those larger trips early before we get all booked up.
Fireworks from Navy Pier: On Wednesday & Saturday nights we offer Sunset & Fireworks cruises that take place just off of Navy Pier about 1 hour after the sun sets.
Experience firsthand the fun and beauty of the city on a Private boat Charter with all your friends and family members. Summer in Chicago is short and boating on Lake Michigan is the perfect way to spend a day with friends in Chicago.

51′ Sea Ray

Time of Operation:
Mid-May through September, we host private charters every day of the week.
Our weekends book up very fast so please don’t wait. We offer discounts for weekday bookings Monday – Thursday.
Time slots:
We offer 4, 6, and 8-hour private charters out of Burnham Harbor. Our charters normally start at 10 AM, 2:30 PM, or 7 PM for our Sunset and fireworks cruises.
* We took Chance The Rapper and his family & Matt Forte and his kids for a Sunset & Navy Pier Fireworks show

You can also find our website at

35′ Sea Ray

Private, Luxurious, and Affordable Yacht Charters in Chicago, IL

Chicago Sailboat and Yacht Charters offer an exclusive and unforgettable experience for those who want to explore Chicago’s magnificent, river, shoreline or the Playpen in the lap of luxury. With our private and affordable yacht charters, you can indulge in the ultimate photo-worthy experience, where our fleet of premium powerboats will take you and your friends on a breathtaking adventure. Each of our boats is tailored to meet your unique needs, with comfortable seating and premium sound systems, all at an affordable cost. Our charters are perfect for impressing clients, hosting unforgettable gatherings, or simply indulging in a romantic evening watching the sunset. If you are looking for a boat or yacht rental in Chicago, IL, to have a great time in the Playpen, look no further than Chicago Sailboat and Yacht Charters. We are one of the premier boat charter companies in Chicago, offering services and amenities that are designed to impress and delight.

Bring a Group to Party in the Playpen!

We know that the best things in life are meant to be shared. That’s why we offer a range of options for group charters, so you can bring together your friends, family, and business colleagues to have a blast in the Playpen. Our fleet of premium powerboats, including a 51′ Searay Sundancer and a 35′ Searay Sundancer, together they can accommodate up to 25 people, allowing you to experience the ultimate in-group fun and adventure. With our Tie-Up in the Playpen option, you can stop and anchor in the world-famous playpen, where you can crank up the sound and chill on our rafts or take a dip in the crystal-clear waters. A group charter with Chicago Sailboat and Yacht Charters is the perfect way to create lasting memories and share unforgettable moments.

The Playpen - Chicago's Popular Boating Place

If you’re looking for a thrilling boating adventure, look no further than the Playpen. With its breathtaking view of the city it’s the perfect location to anchor your boat, jump into the refreshing water, and soak up some sun while sipping on your favorite drink.

The luxurious amenities on our boat will amplify your experience as you feel the breeze blowing through your hair. The dazzling blue waters are ideal for swimming, and you can even climb aboard a floating island to take a break from all the action.

Whether you’re looking for some relaxation or some excitement, the Playpen is the ultimate destination for boating enthusiasts.

Chicago Sailboat and Yacht Charters Offer Priceless Pampered Yachting Experiences

At Chicago Sailboat and Yacht Charters, we pride ourselves on providing our guests with priceless, pampered yachting experiences. We go above and beyond to offer complete luxury, flexibility, and customization, tailoring each of our charters to your unique desires. From taking a cruise down the Chicago River to partying in Lake Michigan’s Playpen to watching the sun go down over the city, our yacht charters will help you do it all in style. At Chicago Sailboat and Yacht Charters, we believe that our guests deserve the absolute best, and we promise to deliver unforgettable, priceless yachting experiences that you’ll treasure for years to come.

Yacht Charters


Nancy M Testimonial Logo
Nancy M Developer

The views of the Chicago skyline were amazing, we can't wait to go again!

Susan W Testimonial Logo
Susan W returning guest

The captain made our trip really fun and educational seeing all the different sights like Navy Pier with its flags flying high was incredible and the views of the Chicago Lighthouse and water Intake cribs up close were amazing.

Steve A Testimonial Logo
Steve A returning guest

Our family had an incredible time sailing on Lake Michigan

Robert S Testimonial Logo
Robert S first time guest

The Fireworks by Navy Pier were incredible especially watching while having dinner and a good beer

Boat Party