Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Map View

Illinois, US Boat Rentals & Yacht Charters

4.9

(6,227 Reviews)

Page 4 of 13 • 302 listings

Events in Chicago · 6 guests

Beautiful 37’ Sea Ray Sundancer Motor Yacht Out of Navy Pier Marina

New

$350+/hour

Limited Availability

Sailing in Chicago · 6 guests

Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

5.0

$450/hour

Events in Chicago · 13 guests

50ft ITALIAN YACHT - ELEGANT DESIGN - LUXURY VIBES - ONLY ONE LIKE THIS IN CHI

5.0

$400/hour

Limited Availability

Powerboats in Chicago · 9 guests

Gorgeous 26ft Chaparral 257SSX Bowrider in Chicago

5.0

$150/hour

Limited Availability

Powerboats in Chicago · 9 guests

Cruise on the New & Luxurious 2024 30ft Chaparral Motor Yacht in Chicago!!!

5.0

$250/hour

Events in Chicago · 8 guests

2015 Absolute 40 STL Motor Yacht for rent in Chicago, IL

5.0

$500/hour

Events in Chicago · 6 guests

"Captain is Free". If you have 6 passengers or less...this yacht is Just Right!!

5.0

$350+/hour

Limited Availability

Events in Chicago · 40 guests

Luxury 45’ Catamaran in Chicago | Up to 40 Guests

5.0

Superowner

Best of 2026

$950/hour

Instant Book

Events in Chicago · 13 guests

60ft Azimut Evolution Double Decker Yacht Charter in Chicago

5.0

Superowner

Best of 2026

$750+/hour

Limited Availability

Events in Chicago · 10 guests

33ft Bayliner Powerboat Charter in Chicago for 10 Guests

4.6

$300/hour

Limited Availability

Events in Chicago · 13 guests

Prestige 550 Flybridge Luxury Yacht Charter in Chicago

5.0

$400/hour

Events in Chicago · 12 guests

Luxury 40' Sea Ray Sundancer Motor Yacht with Premium Sound System in Chicago

5.0

$300/hour

Sailing in Chicago · 13 guests

Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

5.0

$440/hour

Limited Availability

Sailing in Chicago · 6 guests

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

5.0

Superowner

Best of 2026

$220/hour

Events in Chicago · 12 guests

Enjoy the Sun on Lake Michigan with Family or Friends on a 58' Sea Ray Yacht

5.0

$375/hour

Events in Chicago · 12 guests

31ft Sea Ray 310 Sedan Bridge Motor Yacht Private Full Day Charter - Chicago, IL

3.5

$300/hour

Limited Availability

Powerboats in Chicago · 8 guests

Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain

4.4

$250/hour

Limited Availability

Events in Chicago · 13 guests

Private Luxury Charter In Chicago - Sea Ray 360 Sundancer Motor Yacht

5.0

$300/hour

Limited Availability

Events in Chicago · 13 guests

Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

4.9

Superowner

Best of 2026

$235/hour

Events in Chicago · 12 guests

Gorgeous 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing in Chicago

5.0

$500/hour

Powerboats in Chicago · 6 guests

Captained Boat: A perfect blend of comfort & adventure aboard Sea Ray Sundancer

5.0

$235+/hour

Limited Availability

Events in Chicago · 13 guests

38ft 'The Gwen' Carver Mariner Captained Charter With All Amenities In Chicago!

4.9

Superowner

$275/hour

Limited Availability

Events in Chicago · 12 guests

42ft Mainship Party Yacht Chicago Playpen & Fireworks Cruise for 12 Guests

4.3

$350/hour

Instant Book

Water Sports in Chicago · 2 guests

Yamaha WaveRunner FX Cruiser HO Jet Ski Rental in Chicago IL

5.0

$195/hour

Top Destinations Nearby

287
Chicago
Illinois

Illinois Reviews

Patrick

50ft ITALIAN YACHT - ELEGANT DESIGN - LUXURY VIBES - ONLY ONE LIKE THIS IN CHI
Paul and Seba were excellent hosts. The boat was clean, ready to go on time, and exceptionally flexible when we were a little bit late. Additionally they had great suggestions on where to go and how to spend time on the water. We plan to book with them again before the end of the year!
nina

Luxury 45’ Catamaran in Chicago | Up to 40 Guests
the staff is so great. patient, kind and understanding. we made a very last minute booking and they were extremely accommodating and flexible. the service was tremendous. the bathroom was CLEAN. which is huge for a mostly girl group. 12/10, no notes
MF
Maxine

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Nijole was an incredible host/communicator. They made the booking and the trip easy, care-free and relaxing. The boat, The Harmony, was beautiful and clean. My fanily and I had an incredible experience and are excited to book another excursion soon!
KH
Katie

Cruise Lake Michigan aboard 27' Maxum 2400 Motor Yacht with Captain
We had a great experience! Pick up and drop off were super smooth. Boat was the perfect size for our small group. Luis was a super great, fun captain who even took pictures for our group. would definitely book again!
Shericka

Prestige 550 Flybridge Luxury Yacht Charter in Chicago
Armand’s boat is beautiful. It was an exceptional time for a boat outing with friends. It was clean, spacious and the Captain Matt and Danny were helpful and ensured we had a great time! Would rent this boat again!
SC
Santhosh

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
We had a last minute booking and Nicole was kind enough to accommodate us and communication was great. Amazing boat, super friendly couple who are great to have conversations with. They made sure everyone had a great time safely. Highly recommend!