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All listings in Chicago

Search yacht rentals in Chicago, Illinois.

4.9(Average of 2,631 reviews in this area)
Page 1 of 10 (217 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
Best of 2022
$350hour
2018 Beneteau GT 42' "James Bond", book now for Wednesday or Saturday fireworks
Powerboats in Chicago · 12 guests

2018 Beneteau GT 42' "James Bond", book now for Wednesday or Saturday fireworks

5.0
$300hour
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
$240hour
Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht
Powerboats in Chicago · 12 guests

Calling all Aquaholics! Luxury Cruising on Lake Michigan w/ 32' Chaparral Yacht

4.7
$250hour
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 2022
$800hour
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 2022
$350hour
Includes Fuel Sundancer 36' LOA
Events in Chicago · 13 guests

Includes Fuel Sundancer 36' LOA

5.0
$275-300hour
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
**September Special: Chicago Boat Rentals for 12 on Lake Michigan / Play Pen**
Powerboats in Chicago · 12 guests

**September Special: Chicago Boat Rentals for 12 on Lake Michigan / Play Pen**

5.0
$250hour
Fuel Searay  Sundancer Cruiser 36' LOA
Events in Chicago · 13 guests

Fuel Searay Sundancer Cruiser 36' LOA

5.0
$275-300hour
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 2022
$369hour
*** $175 hr***Weekend Charter Rental - 33' Maxum!
Events in Chicago · 10 guests

*** $175 hr***Weekend Charter Rental - 33' Maxum!

4.7
$175hour
52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!
Events in Chicago · 12 guests

52’ Beautiful Sunseeker Portofino Pristine Condition Weekday Special Rates!!

5.0
$250hour
Sea Ray Express 390 Luxury Charter in Chicago, Illinois
Events in Chicago · 12 guests

Sea Ray Express 390 Luxury Charter in Chicago, Illinois

5.0
$300hour
Double Decker 50FT Sea Ray Flybridge Yacht!
Events in Chicago · 12 guests

Double Decker 50FT Sea Ray Flybridge Yacht!

5.0
Superowner
Best of 2022
$400-425hour
42FT Regal Commodore Express Cruiser
Events in Chicago · 12 guests

42FT Regal Commodore Express Cruiser

5.0
Superowner
Best of 2022
$275-375hour
Instant Book
🚤 40' Searay - End of Season Sale - 10% off 🌊
Events in Chicago · 12 guests

🚤 40' Searay - End of Season Sale - 10% off 🌊

4.9
$250hour
Multi Level Luxury Yacht Rental in Chicago - Water toys are included!
Events in Chicago · 12 guests

Multi Level Luxury Yacht Rental in Chicago - Water toys are included!

4.9
Superowner
$199hour
Instant Book
*GORGEOUS* 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing
Events in Chicago · 12 guests

*GORGEOUS* 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing

5.0
$600hour
46ft Sea Ray Sundancer Motor Yacht Rental in Chicago, Illinois
Events in Chicago · 12 guests

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

5.0
$340hour
35' Luxury Double-Decker Yacht Rental in Chicago - Up To 12 Guests!
Events in Chicago · 12 guests

35' Luxury Double-Decker Yacht Rental in Chicago - Up To 12 Guests!

5.0
$325hour
44' Luxury Sea Ray Express Yacht Rental/Party Boat in Chicago, Illinois
Events in Chicago · 12 guests

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

4.9
Superowner
$399hour
44' Luxury Sundancer Yacht Rental! Includes Floating Island!
Events in Chicago · 12 guests

44' Luxury Sundancer Yacht Rental! Includes Floating Island!

4.8
Superowner
$399hour
Gorgeous 40FT Sea Ray - Stunning Interior
Events in Chicago · 12 guests

Gorgeous 40FT Sea Ray - Stunning Interior

5.0
Superowner
Best of 2022
$238hour
Instant Book

Motor Yacht Reviews in Chicago

  1. SC
    Shazaade
    *** $175 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!

  2. sb
    suzanne
    42FT Regal Commodore Express Cruiser

    Great boat, great time! Chris was terrific to work with and boat and experience as pictured and promised. He met us at the dock and was helpful with senior mom and teen kids. Captain Zach very knowledgeable and helpful, too. Would rent again in a heartbeat.

  3. DH
    Denise
    *** $175 hr***Weekend Charter Rental - 33' Maxum!

    We had a blast on this charter for my boyfriend’s birthday Labor Day weekend. Mr.Diggs offers you an affordable price for a luxury experience. Mr. Diggs was also nice enough to wait for my friend who was running late. Scott, our captain, was a lot of fun and blended in with our party nicely.

  4. HS
    Humaa
    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.

    Our group had an amazing time! AD was super nice and the ride down the river was great! We weren't even done with our time and we were already talking about a possible next booking. Cute, intimate area for friends and family!

  5. ES
    Erin
    35' Luxury Double-Decker Yacht Rental in Chicago - Up To 12 Guests!

    Our group of 12 had a great day out on the water! Steve and Helen were incredibly communicative and great to work with, and their boat was great. We had a fantastic time on the lily pad in the water, hanging up top, and chilling on the front of the boat! Brady was our captain, and he was fantastic too. All around highly recommend this boat for your charter!

  6. MD
    Mona
    35' Luxury Double-Decker Yacht Rental in Chicago - Up To 12 Guests!

    We were very impressed with the lovely yacht and also with the excellent communication . Steve and Helen were very quick to respond to all of my questions and concerns. Also, Captain Kevin was very knowledgeable and friendly. Thank you for a memorable experience!