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Gary, Indiana Boat Rentals

Page 1 of 124 listings

eFoil Sessions in Chicagoland!
Adventures in Gary · 6 guests

eFoil Sessions in Chicagoland!

New
$250/hour
36' Cruisers Yacht Captained Pleasure Boat Charter (6 People)
Powerboats in Portage · 6 guests

36' Cruisers Yacht Captained Pleasure Boat Charter (6 People)

New
$300/hour
Cruise Chicagoland from a Beautiful 44ft Maxum Yacht Ready for Sun And Fun
Powerboats in Hammond · 10 guests

Cruise Chicagoland from a Beautiful 44ft Maxum Yacht Ready for Sun And Fun

New
Snoozed - Active 02 Nov 2025
Sea Ray Express Cruiser 340 Luxury Motor Yacht in Chicagoland
Events in Hammond · 8 guests

Sea Ray Express Cruiser 340 Luxury Motor Yacht in Chicagoland

5.0
$250/hour
SeaRay 310 Sundancer  for Rent on Chicago's Lake Michigan
Events in Chicago · 6 guests

SeaRay 310 Sundancer for Rent on Chicago's Lake Michigan

5.0
$325/hour
Explore the Waves with Ease! Rent Your Dream Boat Today!
Events in Chicago · 11 guests

Explore the Waves with Ease! Rent Your Dream Boat Today!

New
$275/hour
33' Bayliner Powerboat for Charter in Chicago
Events in Chicago · 10 guests

33' Bayliner Powerboat for Charter in Chicago

4.6
$295/hour
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
$350+/hour
50' Sea Ray Sundancer -12 Passengers in Chicago, Illinois
Events in Chicago · 12 guests

50' Sea Ray Sundancer -12 Passengers in Chicago, Illinois

4.9
Best of 2025
$350/hour
20' Lund Bass Boat for 3 in Chicago, Illinois
Fishing in Chicago · 3 guests

20' Lund Bass Boat for 3 in Chicago, Illinois

5.0
$67/hour
Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
Events in Chicago · 12 guests

Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience

5.0
$350/hour
55' Carver Cockpit Motor Yacht -12 Passengers in Chicago, Illinois
Events in Chicago · 12 guests

55' Carver Cockpit Motor Yacht -12 Passengers in Chicago, Illinois

4.8
Best of 2025
$350/hour
41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois
Events in Chicago · 12 guests

41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

5.0
Superowner
$350+/hour
Sea Ray Summer Fun In The Sun!
Events in Chicago · 12 guests

Sea Ray Summer Fun In The Sun!

5.0
$350/hour
Luxury 43ft Azimut Atlantis Yacht Charter in Chicago, Illinois
Events in Chicago · 12 guests

Luxury 43ft Azimut Atlantis Yacht Charter in Chicago, Illinois

New
$500+/hour
Chicago’s Casual Lakefront Escape
Events in Chicago · 12 guests

Chicago’s Casual Lakefront Escape

New
$425/hour
Sea Ray Sundancer 290 - Luxury Yacht Rental in Chicago for Events
Events in Chicago · 10 guests

Sea Ray Sundancer 290 - Luxury Yacht Rental in Chicago for Events

New
$325/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' Sea Ray Express Luxury Motor Yacht Rental in Chicago
Events in Chicago · 13 guests

44' Sea Ray Express Luxury Motor Yacht Rental in Chicago

4.8
$349/hour
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
Sea Ray 330 Boat Rental Chicago 12 people
Events in Chicago · 12 guests

Sea Ray 330 Boat Rental Chicago 12 people

5.0
$275/hour
50 ft Double Decker Yacht | Sea Ray Bridge Express
Events in Chicago · 12 guests

50 ft Double Decker Yacht | Sea Ray Bridge Express

2.4
$200/hour
Luxury 40-foot Yacht available to cruise to the Playpen!
Events in Chicago · 12 guests

Luxury 40-foot Yacht available to cruise to the Playpen!

4.8
$275/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

Gary Reviews

  1. RC

    Rachel

    41' Sea Ray Sundancer Motor Yacht for Charter in Chicago, Illinois

    It was great! We ended up having a little later departure and they extended our arrival by the amount of time we missed out on from the departure. Really appreciate all the communication and help from James and his crew! Thank you so much, it was so fun!

  2. KD

    Kevin

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

    Used Captain chris and he was great. I wasn't aware that there was a whole team required (3 people total including captain), not that it mattered much. They tried to not let us use the lilly pad because they said the wind caused it to float away with 8 people on it, but we were in the water and it was great. I would not want to hit the play pen without it IMH. John was very kind, and the boat was quite spacious. Overall had a great experience, 5 stars, but noting the lily hiccup that I felt like I had to fight to keep but it appeared to have no issues using it. Would book again

  3. JD

    Juan

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

    The best charter experience I’ve had! John was amazing, he greeted us at the dock and the crew he recommended was amazing. Captain Ken was the perfect guy for the job, he was fun and a very skilled operator. Deckhands Derroll and G were both great and very personable. Definitely will be booking with John again!

  4. Lawrencia

    Lawrencia

    Double Decker 50FT Sea Ray Flybridge Yacht!

    Boat was nice … I wish it had a little bit of better lighting being that we had a layer charter but other than that everything was perfect :)

  5. Rb

    Raven

    44' Luxury Sundancer Yacht Rental! Includes Floating Island!

    Had an amazing time on our boat charter! From start to finish, everything was smooth, professional, and beyond enjoyable. The crew was friendly, knowledgeable, and made sure we felt safe and relaxed the whole time. The boat itself was spotless and well-equipped, with everything we needed for a fun day on the water. Whether we were cruising, sunbathing, or dropping anchor to swim, it was an unforgettable experience. Highly recommend to anyone looking to escape, unwind, and enjoy a perfect day at sea!

  6. BF

    Bria

    44' Sea Ray Express Luxury Motor Yacht Rental in Chicago

    The boat was clean, the captain was on time and responsive ( so was Jimmy, and everything was as listed in description. We had an incredible time and felt safe and secure the entire time !!!