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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
$90-$900
Sailboats
Set sail with these traditional wind-powered boats
$125-$540
Fishing Charters
Let a captain do the driving while you do the fishing
$25-$345
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$100-$800
Kayaks
Who says you need a motor to have fun on the water?
$10-$250
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
Shannon
'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!
This was our second year in a row booking this boat. They have consistently delivered the best customer service. I have been renting yachts for years and this is the only boat to provide ice and water making the experience very comfortable. I couldn’t recommend them enough!
ED
Emma
28ft. Sea Ray Captained Boat Rental in Chicago
I can’t recommend Captain Memo enough! Not only did he go above and beyond to make my husband and I’s afternoon on his boat an awesome experience, he is also the kindest human! We had so much fun and will definitely be using him again. If you are looking for great captain, he is your guy!
VJ
Vanessa
28ft. Sea Ray Captained Boat Rental in Chicago
There’s not enough words to describe how great our experience was with Captain Memo. His communication was great. He was very knowledgeable of the water. Made our experience very memorable. If you’re looking to experience a wonderful yacht day Book now!!! Thank you Memo for going over and beyond to make sure we felt safe and have good time!!
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.
Brad
Prestige Flybridge 59ft Luxury Yacht Charter in Chicago, Illinois
We have chartered with Armand’s boats multiple times, and they are simply the best. We had an incredible time on “Endeavor” and loved how there were plenty of zones and spaces for everyone to comfortably enjoy their time on the water. We’ll be booking again for sure!
Issam
28ft. Sea Ray Captained Boat Rental in Chicago
⭐️⭐️⭐️⭐️⭐️ We recently had the pleasure of going on a boat tour with Captain Nemo in Chicago, and we can't recommend it highly enough! From the moment we stepped aboard, Captain Nemo made us feel like family. The views of the skyline from the water were absolutely breathtaking, and the boat itself was comfortable and well-maintained. Captain Nemo's attention to detail and commitment to ensuring we had the best experience possible really stood out. Whether you’re a local or just visiting, this tour is a must-do! Thank you, Captain Nemo, for an unforgettable day on the water!
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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October 11, 2021
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Boat Rentals
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Illinois