Quick answer: on our 13-guest bareboat charters, you hire a licensed captain separately and pay them directly — typically $100–$125 per hour before gratuity. On our larger COI passenger yachts, a captain and crew are included. More in our captain & crew FAQs.
Planning a birthday, bachelorette, or day out with friends on a Chicago boat rental? With a captain at the helm, everyone in your group gets to enjoy the day — nobody has to drive.
This guide covers what a boat captain costs in Chicago, how hiring one works with Knot My Boat Charters, the rules for bareboat charters, and what your captain takes care of once you leave the dock.
How Much Does It Cost to Hire a Boat Captain in Chicago?
For our bareboat charters (up to 13 guests), captains typically charge $100–$125 per hour before gratuity. The captain's fee is separate from the boat rental and is paid directly to your captain, so confirm your captain's rate before you hire them.
Charters start at a three-hour minimum, so for a three-hour charter the captain's fee typically comes to about $300–$375 before gratuity. For boat rates by vessel and group size, see our Chicago boat rental prices guide.
How much should you tip your boat captain?
It's customary to tip your hired captain and crew 10%–20% of the boat price — not the captain's hourly rate. Gratuity is paid to your captain directly, along with their fee.
How do you pay a boat captain?
Pay your captain directly. Captains are independent contractors hired by the charterer, so Knot My Boat Charters legally can't accept payment on their behalf. Ask your captain which payment method they prefer when you confirm the hire.
Is a captain included on larger yachts?
Yes. On our COI (Certificate of Inspection) passenger yachts — Amalfi, Sophisticated Lady, and Montauk — a licensed captain and professional crew are included in the charter price and assigned by our team. Crew gratuity is built into the price too, though captains always appreciate an extra tip for great service. Compare the full fleet to see which boats include crew.
Captain Rules for Bareboat Charters
Our 13-guest boats — the 37' through 56' Sea Ray fleet — are bareboat charters. Under U.S. Coast Guard bareboat terms, the charterer is treated as the temporary owner of the vessel for the charter, which is why you hire the captain rather than us:
- You hire the captain. Captains are independent contractors employed by the charterer, not Knot My Boat Charters employees.
- Capacity is 13 guests: one charterer (the renter) plus up to 12 passengers. Infants and children count as passengers.
- Captain and crew don't count toward the 13-guest limit.
Captain requirements
Coast Guard regulations require a licensed captain. The captains on our approved list already know our boats and have completed safety protocol testing with our dock team. If you'd rather bring your own credentialed captain, email their credentials to contact@knotmyboatcharters.com for approval before your charter.
How to Book a Captain for Your Boat Rental
- Book your boat, then choose a captain. Pick a vessel and time on our booking page. After checkout, review our approved captains — all familiar with our vessels — and request one.
- Wait for confirmation. Your first email only means the captain request is pending — it doesn't confirm the captain is available. Allow captains 24–48 hours to respond.
- Connect with your captain. Once a captain accepts, you'll get a confirmation email and can message them directly with questions. If they decline, request another captain from the approved list.
Choose your captain when you book. Captains aren't our employees, so we don't see their schedules, and good-weather weekends fill up fast. If the forecast turns, our weather and cancellation policy explains what happens next.
What Does a Hired Boat Captain Handle?
Your captain operates the boat — navigation, docking, and anchoring — and looks after the safety of everyone aboard, so your group can relax and celebrate. They also know Chicago from the water and can take you to spots you might otherwise miss.
Plan your route with your captain
Before leaving the dock, talk through your plans with your captain. There's a lot to see from the water, and captains can suggest common routes that fit your reservation time. Popular choices include anchoring at the Chicago Playpen and watching the Navy Pier fireworks, which run Wednesday and Saturday nights through the summer.
A Chicago River cruise takes longer, so plan for a longer charter — the river is especially busy Friday through Sunday, when waits at the lock can add time.
On the day of your charter
Stay on top of messages from your captain in the days before your charter. If you're running late, contact your captain first, then call us at (312) 971-0971 so our team can help.
What Guests Say About Our Chicago Captains
David & Carly were the absolute BEST!! So kind and sweet!!! 100% recommend booking with them! We had the best day! They knew the best photo locations while taking the best care of our group(:
— Abby H
Great company to book a boat from. Our captain Tanner was truly the best. He went above and beyond for us and we really appreciated it! Definitely recommend him. Will be booking with him again.
— Nicole H
Knot My Boat Charters and Captain Ian are the best! They were extremely responsive, provided super detailed information throughout the booking process, and created the best bachelorette atmosphere! I would absolutely recommend them to anyone looking to have an awesome day on Lake Michigan.
— Caroline K
I rented a boat with Knot My Boat Charters yesterday and we had a blast! Our captain, Denis, was super professional and supportive getting us out on time. If you're looking for a charter company that has clean, luxury boats then look no further. We highly recommend watching the Navy Pier fireworks!
— Brent W
Still Have Questions About Hiring a Captain?
Our captain cost FAQs cover the details, or reach our team at contact@knotmyboatcharters.com or (312) 971-0971 — we're happy to help you plan your charter.