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Rent a Boat or Yacht in Chicago, Illinois

All Chicago Listings

Page 1 of 12283 listings

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!
Powerboats in Chicago · 12 guests

Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

5.0
$175hour
Stunning 45’ Sea Ray Yacht
Events in Chicago · 12 guests

Stunning 45’ Sea Ray Yacht

5.0
$300hour
Luxury Playpen Lake Michigan Experience
Events in Chicago · 7 guests

Luxury Playpen Lake Michigan Experience

5.0
$275hour
27' Maxum 2400 Motor Yacht Rental in Chicago
Powerboats in Chicago · 8 guests

27' Maxum 2400 Motor Yacht Rental in Chicago

4.3
$200hour
Double Decker 50FT Sea Ray Flybridge Yacht!
Events in Chicago · 13 guests

Double Decker 50FT Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2023
$292hour
Playpen bound on 25' Yamaha Jetboat!
Powerboats in Chicago · 10 guests

Playpen bound on 25' Yamaha Jetboat!

5.0
$225hour
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Events in Chicago · 12 guests

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

5.0
$200hour
Instant Book
25.5 ft. Chaparral SSX257 Luxury Vessel!!
Powerboats in Chicago · 10 guests

25.5 ft. Chaparral SSX257 Luxury Vessel!!

5.0
$200hour
50' Multi-level Luxury Yacht with Party up to 12
Events in Chicago · 12 guests

50' Multi-level Luxury Yacht with Party up to 12

5.0
Superowner
Best of 2023
$300-$350hour
Instant Book
61ft Premier Sea Ray Chicago Playpen, River, Winery
Events in Chicago · 12 guests

61ft Premier Sea Ray Chicago Playpen, River, Winery

5.0
Superowner
Best of 2023
$600hour
Instant Book
LUXURY Awaits on a spacious 38 Foot Yacht!
Events in Chicago · 12 guests

LUXURY Awaits on a spacious 38 Foot Yacht!

New
$250hour
27' Sea Ray Sundance - Extended Swimming Platform
Events in Chicago · 6 guests

27' Sea Ray Sundance - Extended Swimming Platform

5.0
$250hour
20 Passenger Captained Party & Event Boat in Chicago
Powerboats in Chicago · 20 guests

20 Passenger Captained Party & Event Boat in Chicago

5.0
Superowner
Best of 2023
$700hour
Captain Memo's 28 ft. Sea Ray in Chicago
Events in Chicago · 6 guests

Captain Memo's 28 ft. Sea Ray in Chicago

5.0
Superowner
$230hour
Stylish elegance and spacious comfort ... your best time ever!
Events in Chicago · 12 guests

Stylish elegance and spacious comfort ... your best time ever!

5.0
$250hour
Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago
Events in Chicago · 13 guests

Captained charter on 40' Sea Ray Sundancer with all amenities in Chicago

5.0
$275hour
Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
Powerboats in Chicago · 6 guests

Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

5.0
$175hour
Luxurious 60' Yacht with Fly Bridge
Events in Chicago · 12 guests

Luxurious 60' Yacht with Fly Bridge

5.0
$450hour
24 Passenger Captained Party & Event Boat in Chicago!
Powerboats in Chicago · 24 guests

24 Passenger Captained Party & Event Boat in Chicago!

5.0
Superowner
Best of 2023
$800hour
Chicago Summer Vibes - Soak up the Sun in Style!
Powerboats in Chicago · 6 guests

Chicago Summer Vibes - Soak up the Sun in Style!

5.0
$300hour
SeaRay Sundancer 340 Motor Yacht
Events in Chicago · 12 guests

SeaRay Sundancer 340 Motor Yacht

5.0
$250hour
32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Events in Chicago · 6 guests

32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

4.9
Best of 2023
$280hour
BIG BOAT SMALL PRICE EVERYONE CAN ENJOY | 42FT SEA RAY Sundancer Yacht
Events in Chicago · 10 guests

BIG BOAT SMALL PRICE EVERYONE CAN ENJOY | 42FT SEA RAY Sundancer Yacht

5.0
$300hour
Captained charter on 40' Sea Ray with all amenities in Chicago!
Events in Chicago · 13 guests

Captained charter on 40' Sea Ray with all amenities in Chicago!

5.0
$350hour
36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )
Events in Chicago · 6 guests

36' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

5.0
Best of 2023
$440hour
39' Sea Ray for Rent in Chicago, Illinois!
Events in Chicago · 12 guests

39' Sea Ray for Rent in Chicago, Illinois!

5.0
$350-$400hour
BIG BOAT SMALL PRICE EVERYONE CAN ENJOY | 45FT Sea Ray 400 Express Cruiser
Events in Chicago · 10 guests

BIG BOAT SMALL PRICE EVERYONE CAN ENJOY | 45FT Sea Ray 400 Express Cruiser

5.0
$300hour
Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat
Events in Chicago · 12 guests

Diversey Harbor 46 ft Luxury Yacht Perfect Play Pen Boat

5.0
$200hour

Chicago Reviews

  1. JT

    Julianne

    Captain Memo's 28 ft. Sea Ray in Chicago

    Could not recommend Captain Memo enough! He was absolutely fantastic and went above and beyond to make sure that we had the best day on the water. While booking with him and coordinating the spot to meet up, he was extremely communicative and responsive. His boat was very clean and equipped with a great sound system, a spacious cooler and all the water floats we could want. He was helpful, fun and engaging the whole time we were out. If you are looking for a boat for a day out on the lake- look no further, you won't find anyone better than captain memo! 10 stars!!

  2. Mardysa

    Mardysa

    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

    I had an amazing time! I booked on rather short notice and Kevin came through for me especially with helping to find a captain for such a busy day. The entire process was smooth and Captain Lisa was great! I’d definitely book with him again in the future.

  3. karina

    karina

    Diversey Harbor 36' Sea Ray Floating Oasis for your Unforgettable Celebrations!!

    Kevin was super nice and accommodating. Any question I asked he answered. Was able to provide me a captain on short notice. The boat itself was super clean! Even the bathroom. And it was a full bathroom. Very happy with purchase and experience. Thank you kevin!

  4. Michael

    Michael

    25.5 ft. Chaparral SSX257 Luxury Vessel!!

    Awesome clean boat. Easy to drive and work with and all necessary amenities. Had awesome time at playpen with 5 of my friends but could easily fit a lot more. Eduard was easy to work with and made it a seamless experience.Next time coming to Chicago I will definitely be coming to him if I need a boat for the summer.

  5. DJ

    Dana

    32' Motor Yacht Charter Downtown Chicago's Lake Front ( CAPTAIN INCLUDED )

    We had an absolutely unforgettable boating experience. Adnan's larger boat was amazing, very spacious and it provided plenty of room to relax. We have amazing pictures to cherish from our time on board. Our captain was fantastic as well. We enjoyed his company. Additionally, the owner was incredibly accommodating when we had a change in plans, making the experience even smoother. We can't wait to book another outing—highly recommended for anyone seeking a memorable day on the water!

  6. LZ

    Linda

    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

    Our trip with Tamer was fantastic!! He is such a nice, chill guy. Was easy to communicate with, flexible, and helpful! We loved his clean and comfortable boat, his great floaties, the snacks, drinks, and even seasickness medication! He helped us create an itinerary for how to use our time and the entire experience was beautiful, relaxing, and comfortable! I would definitely book with him in the future!