How Playpen Chicago Works
Three simple steps between you and an unforgettable day on Lake Michigan.
Browse & Choose
Tell us your occasion, date, and group size. We’ll show you the perfect vessels with transparent all-in pricing.
Book & Customize
Secure your charter with a 50% deposit. Add a captain, catering, photography, or a DJ to make it unforgettable.
Board & Enjoy
Meet your captain at the marina. Waivers are done digitally. All that’s left is the skyline.
Frequently Asked Questions
What if it rains?
Your captain has final authority on safety. If weather forces a cancellation, you receive a full refund or a free reschedule within 90 days. We monitor forecasts and notify you in advance whenever conditions look uncertain.
Do I need boating experience?
Not at all. Most of our charters include a credential-verified captain who handles everything on the water. You’re free to sit back and enjoy the ride.
How many guests can I bring?
Group capacity depends on the vessel. Our fleet ranges from intimate 6-passenger boats to large yachts that accommodate 40+ guests. Each listing shows its exact USCG-rated capacity.
Have more questions? Visit our Help Center