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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$605
Fishing Charters
Let a captain do the driving while you do the fishing
$40-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$40-$200
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$200
Kayaks
Who says you need a motor to have fun on the water?
$25-$275
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$140-$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$110
Sailboats
Set sail with these traditional wind-powered boats
$325
JG
Jack
Burnham Harbor, CAPTAIN/FUEL INCLUDED
We had an unforgettable experience with Captain Joe and deckhand Ryan! They were incredibly accommodating and flexible, adjusting our itinerary to work around storms so we could still make the most of the day. Their professionalism and positive energy made the entire trip a blast—we were celebrating my 30th birthday, and it couldn’t have been better. The float tube was a huge hit and added so much fun to our time on the water. Highly recommend booking with them—would absolutely do it again!
ED
Ellery
Chicago Luxury Boat Rental
I can’t rave enough about our boat experience! From start to finish, Captain José and Captain Savage were absolutely amazing. Even with some weather conditions, they kept us in the loop and made sure we were safe, comfortable, and having a blast the entire time. Communication was on point! The crew? ICONIC. So fun, so high-energy, and just the vibe you want when you’re out celebrating. They truly made my birthday unforgettable. They even let us DJ, so we had full control of the party playlist—and trust me, we took full advantage. Everything felt super personalized, attentive, and just full of good vibes. Would 1000% book again. THANK YOU for the epic memories!
LH
Lauren
Experience Lake Michigan like never before on Beautiful 35ft Maxum
We had Jay as our captain and he was so sweet and helpful. It was a crazy day with rain and weather but he did all he could to make sure we still had fun and we were safe at the same time! It was a gorg lil boat. Overall amazing experience!
OT
Olivia
Stunning 45’ Sea Ray Yacht
Fantastic Experience with Peter and Team! Peter was incredible—he even met us in the parking lot with a wagon to help transport our drinks and food. He was extremely friendly and communicative from start to finish. My coworkers and I had an amazing time cruising around the lake. The only minor downside was needing to bring our own ice, but everything else was absolutely 10/10. We’ll definitely be booking with Peter and his team again!
JR
Joyce
Chicago Luxury Boat Rental
The weather was challenging, but the crew prioritized our safety and were really flexible to ensure that we had a great experience despite nature's impact. The crew was professional and attentive, the boat was comfortable, and had all the amenities listed. I had a wonderful day.
TJ
Thea
Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht
My friends and I had such a great time on this yacht! The yacht was spacious and clean, perfect for our group to relax and enjoy the day. Everything went smoothly from booking to the very end. Kevin’s customer service was hands down the BEST I’ve experienced. He was responsive, helpful, and kept us informed every step of the way. Our captain, Evan, was just as amazing! The ride was smooth, safe, and so much fun. I highly recommend booking with Kevin, and I’ll absolutely book with him again when I return. Thanks for everything!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!