List Your Boat on Playpen Chicago
Turn your vessel into a revenue-generating asset. Set your own rates, manage your calendar, and connect with premium charter guests on Lake Michigan.
How It Works
Five steps from sign-up to your first payout.
List
Create your listing with photos, specs, and pricing. Describe your vessel, its amenities, and what makes it a great charter experience on Lake Michigan.
Get Verified
Submit insurance, permits, and documentation for compliance review. Our team verifies every credential before your listing goes live.
Set Pricing
Configure your rates by day, occasion, and season. You control every price point — base hourly, half-day, full-day, weekend multipliers, and occasion premiums.
Accept Bookings
Review and accept charter requests on your schedule, or enable instant booking for qualified renters. You decide who charters your vessel.
Get Paid
Receive payouts via Stripe after each completed charter. See exactly what you earned, what was deducted, and when it arrives in your account.
Your Pricing, Your Control
You set every rate. We never override your pricing.
Base Rates
Set your hourly rate, half-day (4hr), and full-day (8hr) pricing independently.
Day of Week
Different rates for weekday vs. weekend vs. Friday. Charge what each day is worth.
Occasion Type
Premium pricing for birthday, bachelorette, corporate, proposal, and holiday charters.
Peak Dates
Override rates for July 3–4, Air & Water Show weekend, Labor Day, Memorial Day, and Black Yacht Weekend.
Time of Day
Evening and sunset premium surcharges for high-demand departure times.
Minimum Booking Hours
Configurable per day type — e.g., 2hr weekday minimum, 4hr weekend, 6hr holidays.
Lead-Time Pricing
Optional surcharge for bookings within 72 hours. Optional discount for last-minute fill to maximize utilization.
Your floor price is your floor. No automated discounting below it.
Cancellation Policies
You choose the policy that fits your business. Higher-end vessels often use Stringent; operators who want maximum bookings use Flexible.
| Flexible | Medium | Stringent | |
|---|---|---|---|
| Full refund | 7+ days before | 14+ days before | 30+ days before |
| 50% refund | 3–7 days | 7–14 days | 14–30 days |
| No refund | Under 3 days | Under 7 days | Under 14 days |
Weather cancellations are separate and governed by our Weather Policy.
If you cancel a confirmed booking, the renter receives a full refund.
What You Need to Get Started
Complete these requirements before your listing goes live.
Getting Paid
Payouts are processed via Stripe Connect after each completed charter.
Payout Timeline
3–5 business days after trip completion. Funds are deposited directly to the bank account linked in your Stripe Connect dashboard.
Security Deposit Hold
Pre-authorization hold is released 48 hours post-trip if no damage claim is filed. If damage occurs, the hold is captured for valid claims with photo evidence.
Earnings Dashboard
Your dashboard shows earnings by period, pending payouts, completed payouts, and revenue by vessel — all in one place.
Full Transparency
You see exactly what you earned, what was deducted, and when it hits your account. Every payout includes a booking reference and itemized breakdown.
Tax Obligations
You are an independent contractor, not an employee of The Playpen Enterprises LLC. All income earned through the platform is reported to you and to the IRS as required by law.
1099-NEC: Issued if your annual earnings exceed $600 (federal threshold). Illinois state threshold for 1099-K via Stripe is $1,000.
W-9 Required: You must submit a W-9 during onboarding. Payouts are blocked until your W-9 is on file.
Your Responsibility: You are responsible for your own income tax filings, estimated quarterly payments, and any applicable state/local taxes.
Consult your tax advisor for guidance specific to your situation.
First 3 Completed Charters — Commission-Free
Qualifying vessels pay zero commission on their first three completed charters. This is our investment in building Chicago ’s best charter fleet from the start.
Listing Tiers
Tier assignment is reviewed quarterly based on performance metrics.
Standard Listing
- ✓All compliance documentation verified
- ✓Safety equipment attestation
- ✓Minimum 8 professional photos
- ✓Acceptable response time
Standard listing placement
Priority Placement
- ✓Everything in Verified
- ✓Professional media (photo + video)
- ✓4.5+ rating after 10 trips
- ✓Under 5% cancellation rate
- ✓Stronger amenities package
- ✓Flexible or Medium cancellation policy
Priority placement · Eligible for Featured Experiences
Premium Placement
- ✓Everything in Signature
- ✓Concierge-supported bookings
- ✓Private-event ready
- ✓Premium crewing
Premium placement · Featured in Collections
Your Dashboard
Everything you need to manage your charter business in one place.
Calendar Management
Sync with iCal, block dates, and set your availability windows. Prevent double-bookings across platforms with automatic calendar sync.
Booking Requests
Accept or decline charter requests with response time tracking. Your response rate affects your listing visibility and tier standing.
Earnings
Revenue breakdowns by period, vessel, and booking source. See your gross earnings, commission deductions, and net payouts at a glance.
Compliance Documents
Insurance expiry alerts, permit renewal reminders, and document status tracking. Stay compliant without the paperwork headache.
Payout History
Every payout with its booking reference, amount, deductions, and deposit date. Full audit trail for your records and tax filings.
Performance Analytics
Booking conversion rate, average response time, rating trends, and seasonal demand patterns for your vessel type and size.
Insurance Explained
Why Additional Insured Matters
When your insurer names The Playpen Enterprises LLC as Additional Insured, it extends your policy’s protection to cover the platform’s role in facilitating the charter. This is standard in commercial charter operations and protects both parties in the event of a claim.
How to Get It
Contact your marine insurance provider and request a Certificate of Insurance (COI) with The Playpen Enterprises LLC listed as Additional Insured. Most insurers process this in 2–3 business days. There is typically no additional cost for this endorsement.
What It Covers
Third-party liability claims arising from charter operations on your vessel. This does not replace your own hull or P&I coverage — it extends your existing liability protection to include the platform as an interested party.
Frequently Asked Questions
Ready to List Your Boat?
Join Chicago’s premium charter marketplace. Your vessel, your rates, your schedule.
List Your BoatQuestions? Call (312) 776-3311 or email owners@chicago.theplaypen.com