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Starting at $200 per hour (boat only), you have the option to hire a captain (not included) and will pay the captain directly 

Looking for the fastest way to the playpen? Our power boat is SUPER wide and provides an open social space for up to 12 guests. Equipped with a BANGING sound system, full kitchen and bathroom, and huge swim platform, our 40 foot power boat is sure to be a hit with your friends or colleagues. 



Starting at $150 per hour, (boat only) you have the option to hire a captain (not included) and will pay the captain directly. 

If you are looking for an affordable, relaxing experience choose our sailboat! Large enough to fit up to 10 guests, our 40 foot sailboat is an excellent choice for your seaworthy crew.  Trim the sails and feel the power of the wind propel you through the waves. A true adventure awaits!

the bachelorette


"The boat was much larger then the pictures showed and we had plenty of room to move around. It was very comfortable and had a great sound system, I couldn't have asked for a better time at the Playpen." 


September 2018

"Patrick was a great captain, the boat was clean and the perfect size for our group."


August 2018

"Our group had a great day sailing on Chris's boat. He was responsive, professional, and the boat was in fantastic condition. Looking forward to next time!"


August, 2018

chicago yachting

Our boats are located at

31st Street Harbor

3155 S. Lake Shore Drive

Chicago, IL 60616

Private yacht charters

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© 2019 by Chicago Yacht Charters, LLC