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.
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
Private, Luxurious, and Affordable Yacht Charters in Chicago, IL
Bring a Group to Party in the Playpen!
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.