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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,135
Sailboats
Set sail with these traditional wind-powered boats
$130-$540
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$345
Kayaks
Who says you need a motor to have fun on the water?
$10-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$800
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$300
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$350
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$800
TK
Taran
Chicago Luxury Boat Rental
My girls and I book this boat for a little day out, and it was more than perfect! Captain Jose and Captain Tony were so sweet and attentive and constantly communicated how the weather was looking and our plan. The boat was bigger than we thought and such a nice surprise. I could not recommend Captain Savage more!
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!
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!
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!
MG
Mariah
Stunning 45’ Sea Ray Yacht
Eugene’s communication was 10 out of 10!! He was clear with all his direction and was so polite to me. CAPTAIN PETER was also amazing. If you guys want a chill and fun captain, book PETER! He was so fun and nice.
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.
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!
April 17, 2024
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August 24, 2023
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May 03, 2023
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October 11, 2021
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March 27, 2020
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August 01, 2023
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