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Rent a Boat or Yacht in Chicago, Illinois

4.9(Average of 4,246 reviews in this area)
Page 1 of 12 (269 listings)
Charter a 39' Luxury SeaRay Sundancer 390 for 11 guests w/ Captain in Chicago
Events in Chicago · 11 guests

Charter a 39' Luxury SeaRay Sundancer 390 for 11 guests w/ Captain in Chicago

5.0
$350hour
CAPTAIN MEMO'S 28 ft. SEA RAY AFFORDABLE BOAT RENTAL!
Events in Chicago · 6 guests

CAPTAIN MEMO'S 28 ft. SEA RAY AFFORDABLE BOAT RENTAL!

5.0
Superowner
$230hour
2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024
Events in Chicago · 12 guests

2018 Beneteau GT 42' "James Bond", Book Now for Summer 2024

5.0
$300hour
Maxum 2400 Motor Yacht Rental in Chicago, Illinois
Powerboats in Chicago · 8 guests

Maxum 2400 Motor Yacht Rental in Chicago, Illinois

3.5
$150hour
32' Motor Yacht Charter Downtown Chicago's Lake Front, Relax And Enjoy The Day With Family And Friends! rate Includes fuel, cleaning and Captain fee.
Events in Chicago · 6 guests

32' Motor Yacht Charter Downtown Chicago's Lake Front, Relax And Enjoy The Day With Family And Friends! rate Includes fuel, cleaning and Captain fee.

4.9
Best of 2023
$240hour
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
Best of 2023
$220hour
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 10 guests

2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!

5.0
Superowner
Best of 2023
$350hour
24 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 24 guests

24 Passenger Captained Party & Event Boat in Chicago, Illinois!

5.0
Superowner
Best of 2023
$800hour
65' Skipperliner Huge Party Boat, 6 Guests
Powerboats in Chicago · 6 guests

65' Skipperliner Huge Party Boat, 6 Guests

New
$1,267-$1,400hour
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-$399hour
52' Cruisers Yachts 500 Express Luxury Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

52' Cruisers Yachts 500 Express Luxury Yacht Rental in Chicago, Illinois

New
$750hour
Super Fun and Safe 36' Polynesian Party Boat For 6 People in Chicago, Illinois
Powerboats in Chicago · 6 guests

Super Fun and Safe 36' Polynesian Party Boat For 6 People in Chicago, Illinois

New
$325hour
20 Passenger Captained Party & Event Boat in Chicago, Illinois!
Powerboats in Chicago · 20 guests

20 Passenger Captained Party & Event Boat in Chicago, Illinois!

5.0
Superowner
Best of 2023
$700hour
Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois
Tours in Chicago · 9 guests

Wellcraft Eclipse 233 Cuddy Cabin in Chicago, Illinois

5.0
$250hour
$200 Captain Included. 2021 Yamaha.  Playpen, Fireworks, Skyline Cruises
Powerboats in Chicago · 6 guests

$200 Captain Included. 2021 Yamaha. Playpen, Fireworks, Skyline Cruises

5.0
$200hour
Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!
Powerboats in Chicago · 7 guests

Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

5.0
$150hour
44' Sea Ray Express Luxury Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

44' Sea Ray Express Luxury Motor Yacht Rental in Chicago, Illinois

4.8
Superowner
$399hour
33' Formula Motor Yacht, Great for Playpen!
Events in Chicago · 10 guests

33' Formula Motor Yacht, Great for Playpen!

5.0
$150hour
*** $199 hr***Weekend Charter Rental - 33' Maxum!
Events in Chicago · 10 guests

*** $199 hr***Weekend Charter Rental - 33' Maxum!

4.8
$175hour
40ft Got a Life Formula 40 PC Motor Yacht Rental in Chicago, Illinois
Tours in Chicago · 12 guests

40ft Got a Life Formula 40 PC Motor Yacht Rental in Chicago, Illinois

5.0
Superowner
Best of 2023
$369hour
**Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**
Events in Chicago · 12 guests

**Affordable Luxury Chicago Boat Rentals for 12 on Lake Michigan / Playpen**

5.0
Best of 2023
$250hour
Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL
Events in Chicago · 13 guests

Captained Charter on 38’ Carver Mariner with all the Amenities in Chicago, IL

4.9
Superowner
$275hour
“ Funtime1”  - 20 passengers Party Boat - Playpen or River trips
Powerboats in Chicago · 20 guests

“ Funtime1” - 20 passengers Party Boat - Playpen or River trips

5.0
Superowner
Best of 2023
$700hour
35' Sea Ray SLX Motor Yacht Charter in Chicago
Events in Chicago · 12 guests

35' Sea Ray SLX Motor Yacht Charter in Chicago

5.0
Superowner
Best of 2023
$369hour
70' EXCLUSIVE Motor Yacht NEW to Chicago
Events in Chicago · 13 guests

70' EXCLUSIVE Motor Yacht NEW to Chicago

4.8
Superowner
$999hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200hour
27' Chris Craft  with Water Toys plus Jet Ski Available
Powerboats in Chicago · 6 guests

27' Chris Craft with Water Toys plus Jet Ski Available

5.0
Superowner
Best of 2023
$205hour
Includes Fuel Sundancer 36' LOA
Events in Chicago · 13 guests

Includes Fuel Sundancer 36' LOA

5.0
$275-$300hour

Chicago Reviews

  1. SC
    Shelby
    *** $199 hr***Weekend Charter Rental - 33' Maxum!

    This was the perfect experience for our girls weekend. The boat was exactly what we expected based on the listing. Chad was easy to work with and helpful when I had questions. We booked just a day before we wanted to hit the water so didn’t expect the best, but we had a phenomenal time. Our captain was great too, who was recommended by Chad. We will definitely do this again!

  2. SC
    Shazaade
    *** $199 hr***Weekend Charter Rental - 33' Maxum!

    Mr. Diggs was awesome and our captain, Darrian, was just as great! Communication was quick and clear with both of them. I celebrated my birthday with a few friends and they all had a blast. Darrian matched our vibe, and the boat itself was clean with a great sound system! This was the perfect way to close out Summertime Chi 2023. We’ll definitely be booking with Mr. Diggs next summer!

  3. AP
    Alan
    Sea Ray Cuddy Cabin Boat for Rent on Lake Michigan!

    My husband and I reserved an afternoon on the water with Tamer for our anniversary, and it did not disappoint. As our captain and the owner of the boat, Tamer was the perfect balance of being laid-back and easy-going yet attentive. He was super communicative from the get-go, and his primary concern was making sure we enjoyed our ride while also keeping us safe. Though we brought our own drinks and snacks, he also stocked a complimentary selection of his own that he made available to us, and he even allowed us to bring our two small dogs aboard for the day who both enjoyed being out on the water. We cruised the entire Chicago River through the downtown and out into Lake Michigan, and never once did he make us feel like we were being kept to a time or schedule. In fact, we spent probably an extra hour riding around. Between all that, the boat itself (which was kept clean, in great condition and perfect for a small group), etc., it was an awesome way to celebrate our day and we'd happily book again with Tamer.

  4. David
    David
    Charter a 39' Luxury SeaRay Sundancer 390 for 11 guests w/ Captain in Chicago

    Capt John and his boats/deckhands/captains are all great! Very easy to communicate with and get all the insights you want. We had 2 families with 5 kids overall and it was a great trip. We booked on Chicago Scene day and we were able to see some of the fun, but we also stayed further away from the main playpen. Capt had to dock up once to let off some family members early on the trip and it was seamless. The Sundancer is in great condition and a lot of fun to be on. Highly recommend.

  5. Okoye'
    Okoye'
    CAPTAIN MEMO'S 28 ft. SEA RAY AFFORDABLE BOAT RENTAL!

    Memo is absolutely amazing! Please believe every great review left. He gives outstanding instructions as to where and how to find his boat. He had a cooler, floats, a large speaker- essentially everything we needed. My friends and I had a great time and will be back!

  6. Molly
    Molly
    CAPTAIN MEMO'S 28 ft. SEA RAY AFFORDABLE BOAT RENTAL!

    Captain Memo made this experience unforgettable, just like the name of his boat! He made sure we knew exactly where to meet him at the time of departure, supplied coolers and ice for us and had all the lake floats blown up and ready for us to relax in the lake. He is trustworthy and all around a great guy. Thank you Captain Memo for an unforgettable time!!