Chicago Playpen
Playpen trips anchor off the skyline for a day of swimming, music and relaxing on Lake Michigan.
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Overview
Made for
The packages
Playpen trips anchor off the skyline for a day of swimming, music and relaxing on Lake Michigan.
River cruises pass the Wrigley Building, Tribune Tower and Marina City from the water.
The styles
Amalfi is a 78' power catamaran, a USCG-inspected commercial yacht used for corporate events, weddings and private parties.
A 72' Chris Craft moored at Burnham Harbor, the Sophisticated Lady is a USCG-inspected commercial yacht for up to 49 passengers.
Montauk is a power catamaran that accommodates up to 49 passengers.
Below deck are a wood-finished saloon, galley, wet bar, two staterooms and two full bathrooms.
Guests have room to relax and socialize in a roomy cockpit with comfortable seating.
A wide-open cockpit and generous bow seating give the group room to spread out and see the skyline.
Known for a large open cockpit and cabin floorplan, suited to social events, birthdays and bachelorette parties.
Features upgraded JL Audio Bluetooth sound, a starboard-facing U-shaped seating area and a full-size cabin with bathroom.
Has an upgraded JL Audio Bluetooth sound system, a cockpit and a cabin with one stateroom, one bathroom and a kitchenette.
Event experiences
How it works
Choose Your Chicago Boat or Yacht
Guests select from 23 yachts, ranging from 13-passenger cruisers to event yachts for up to 125 guests.
Pick Your Date and Duration
At least three hours are booked, on Lake Michigan, the river or the Playpen.
Show Up, Meet the Captain, Set Sail
Guests go to the harbor, meet the captain and cast off.
How is booking different for members
Members reserve outings against their allocation through a member booking portal showing live availability.
Details from knotmyboatcharters.com
Good to know
as of September 2026 — verify on the operator’s site