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Browse Illinois Boat Rentals.

Page 2 of 12279 listings

35' Sea Ray SLX Motor Yacht Charter in Chicago
Events in Chicago · 13 guests

35' Sea Ray SLX Motor Yacht Charter in Chicago

5.0
$250/hour
'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!
Events in Chicago · 13 guests

'The Gwen' 38’ Carver Mariner Captained Charter with all amenities in Chicago!

4.9
Superowner
$275/hour
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 13 guests

46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois

5.0
Superowner
$300/hour
Limited Availability
25ft Rinker - Captained included in price- Chicago
Powerboats in Chicago · 8 guests

25ft Rinker - Captained included in price- Chicago

4.9
Superowner
$199/hour
High Demand
Double Decker 50FT Sea Ray Flybridge Yacht!
Powerboats in Chicago · 13 guests

Double Decker 50FT Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2025
$292/hour
40' Luxury Cruiser Yacht for Charter in Chicago
Events in Chicago · 12 guests

40' Luxury Cruiser Yacht for Charter in Chicago

4.9
$300/hour
Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht
Events in Chicago · 12 guests

Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

4.9
Superowner
Best of 2025
$200/hour
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

4.9
Superowner
$240/hour
Limited Availability
Luxury 31ft Bayliner 3055 Ciera for your Playpen Party
Events in Chicago · 8 guests

Luxury 31ft Bayliner 3055 Ciera for your Playpen Party

5.0
$180/hour
High Demand
Maxum Yacht 44' in Chicago
Powerboats in Chicago · 13 guests

Maxum Yacht 44' in Chicago

4.9
Superowner
Best of 2025
$268/hour
44' Luxury Sundancer Yacht Rental! Includes Floating Island!
Events in Chicago · 12 guests

44' Luxury Sundancer Yacht Rental! Includes Floating Island!

4.7
$349/hour
44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
Events in Chicago · 13 guests

44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois

4.9
$349/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Best of 2025
$200/hour
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 2025
$300/hour
Instant Book
2018 Luxury Sea Ray 31 SLX in Chicago up to 10 guests!!
Events in Chicago · 11 guests

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

5.0
$250/hour
Double Decker 50ft Sea Ray Flybridge Yacht!
Events in Chicago · 13 guests

Double Decker 50ft Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2025
$292/hour
Luxury 29ft Crownline Bowrider 285 SS
Powerboats in Chicago · 10 guests

Luxury 29ft Crownline Bowrider 285 SS

5.0
$250/hour
SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

SeaRay Sundancer 35' Motor Yacht Rental in Chicago, Illinois

4.9
$200/hour
38-ft Party Pontoon for Up to 20 Guests in Chicago
Powerboats in Chicago · 20 guests

38-ft Party Pontoon for Up to 20 Guests in Chicago

5.0
Superowner
Best of 2025
$680/hour
Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago
Events in Chicago · 20 guests

Captained Charter on 60ft Martini Sea Ray Luxury Motor Yacht in Chicago

4.8
$1,500/hour
Special End of Season Sunday pricing for 8 to 13 passengers
Sailing in Chicago · 13 guests

Special End of Season Sunday pricing for 8 to 13 passengers

5.0
$550/hour
39' Sea Ray for Rent in Chicago, Illinois!
Events in Chicago · 12 guests

39' Sea Ray for Rent in Chicago, Illinois!

5.0
$350+/hour
Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!
Events in Chicago · 12 guests

Chicago summer in style - 33' Monterey 302 for Charter on Lake Michigan!

4.9
$250/hour
42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!
Events in Chicago · 12 guests

42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!

5.0
$200/hour

Top Destinations Nearby

Illinois Reviews

  1. Ravid

    Ravid

    38-ft Party Pontoon for Up to 20 Guests in Chicago

    My friends and I had an amazing time on Captain Greg's boat! The boat had speakers, cooler, a bathroom, floaties, pretty much everything we needed. The boat was very spacious and comfortable. The crew were very friendly and welcoming as well! We had so much fun sailing around Chicago and swimming in the lake, it was a perfect boating experience!

  2. NV

    Natalie

    25ft Rinker - Captained included in price- Chicago

    Highly recommend Joe and his boat! He made my birthday so special. The boat is equipped with everything you may need - ice and a cooler. And of course, all the toys for the water. The views were spectacular and he recommended doing a cruise before anchoring and getting in the water which we loved. The speaker is also so nice to listen to your favorite tunes!!

  3. LV

    Louie Chelle

    42' Luxury Mediterranean Yacht - 3 Boats Available! Discount on Weekdays!

    We had an amazing time on Captain John's yacht! The boat was very nice, spacious, and exactly as described. It was perfect for a group of girls celebrating a college reunion! Captain John helped coordinate and get us set up right before takeoff, then we had Captain Dee and Hussein with us for the ride. They were all great and courteous! FYI - you will need to reach out to their list of captains to confirm (this was told to us the week of), but honestly, it sounded like they made sure someone was available regardless, so likely a formality. Definitely would book again for future Chicago trips!

  4. MS

    Michael

    Diversey Harbor Gorgeous 46' Sea Ray Luxury Yacht

    I had some friends visiting Chicago and wanted to impress them. Renting a boat from Kevin was the crown jewel of the weekend! Our captain Evan was very professional, accommodating and friendly. The boat exceeded expectation. Would definitely book with them again!

  5. ED

    Elena

    40' Luxury Cruiser Yacht for Charter in Chicago

    We had the BEST time aboard Captain G’s boat thanks to Captain TJ & Deckhand Eric!!! Such a perfect sized boat for 12 people with awesome speakers & storage. Captain TJ was so fun and took some amazing photos/videos while we thoroughly enjoyed the playpen! Can’t wait to book them again next summer and would 11/10 recommend!!! 🙌⛵️❤️

  6. JO

    Jessica

    Maxum Yacht 44' in Chicago

    My friends and I plan a summer boat day every year. I got in contact with Chris who was very responsive from the start and very helpful through the entire booking. We reached out to captain Dan Chavez and I was so happy that we did. He made the experience amazing and was very attentive throughout our time. He prioritized our safety and had gave us a great time. Would mostly highly recommend for an amazing time!