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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$1,135
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$180-$1,050
Sailboats
Set sail with these traditional wind-powered boats
$130-$535
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$200-$800
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$350
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
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$130-$195
Kayaks
Who says you need a motor to have fun on the water?
$120
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!
CP
Chrystal
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
This was an Amazing event. The 46 ft Sea Ray was everything and more. From the Bow to the Stern, five ***** accommodations. Touring on the Chicago Lake against the Chicago Skyline, the scenery was breathtaking, the food was on point, and the bottomless mimosas had us feeling like we were vacationing on the French Riviera. IF you're looking for more than a boat ride, but an experience, book it. As you can see from the photos, this was indeed the ultimate Surprise Birthday Celebration, with a vibe. THANKS to the Owner, Kevin, for making this possible, and to Captain Justin for holding strong to that steering wheel.
DC
Daniela
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
We had an incredible experience with this boat rental! The service and communication were seamless from start to finish—everything was clear, timely, and super easy to coordinate. We were lucky to have Captain Jaydenn onboard with us, and he was absolutely amazing—professional, fun, and made sure we had a great time out on the water.
Emily
44' Italian Luxury Azimut Premier Party Yacht 13 ppl plus Jet Ski Available
Captain Tim was amazing! He was super communicative, fun, patient, and just a great captain overall. Everybody had a great experience on the boat and absolutely loved it! The boat itself was also gorgeous. We would definitely book with Captain Tim again.
MP
Mercedes
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Zach was great and the bachelorette party we had good time on the water watching the fire works and listening to music. Definitely would do this again if I am back in Chicago.
Dapo
Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Booking with Kevin was easy and convenient, providing a great experience. Captain Zach was amazing. If you have any doubts, just book the boat—you'll have an incredible time on the water like we did. I'll definitely book again.
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!