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Illinois, US Boat Rentals & Yacht Charters

4.9

(6,111 Reviews)

Page 13 of 13 • 303 listings

Limited Availability

Events in Chicago · 6 guests

31ft Cabin Cruiser Yacht Charter with USCG Master Captain On Lake Michigan

New

$300/hour

Powerboats in Waukegan · 4 guests

Explore Lake Michigan with the 27’ Bayliner Ciera Sunbridge Yacht from Waukegan

New

$350/hour

Limited Availability

Events in Chicago · 13 guests

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat

5.0

$225/hour

Limited Availability

Events in Chicago · 13 guests

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!

5.0

$225+/hour

Adventures in Illinois · 1 guest

Single Kayak Daily Rental at Starved Rock Campground

New

$69/day

Adventures in Illinois · 2 guests

Tandem Kayak Daily Rental at Starved Rock Campground

New

$75/day

Limited Availability

Powerboats in Chicago · 9 guests

Gorgeous 26ft Chaparral 257SSX Bowrider in Chicago

5.0

$150/hour

Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

4.9

Snoozed - Active 15 Jul 2026

Limited Availability

Events in Chicago · 12 guests

Top of the line Sea Ray Sundancer 340 Motor Yacht - Accommodate 12 Guests

3.8

Snoozed - Active 18 Jul 2026

Events in Chicago · 12 guests

Captained Charter: 36ft Carver Mariner Motor Yacht In Chicago

4.9

Snoozed - Active 25 Jul 2026

Powerboats in Chicago · 7 guests

Unique Experience with our Sea Ray 330 Sundancer Yacht for 7 Guests in Chicago

5.0

Snoozed - Active 02 Jan 2027

Events in Chicago · 12 guests

51ft Sea Ray Sundancer Yacht at Diversey Harbor!

5.0

Snoozed - Active 02 Jan 2027

Events in Chicago · 13 guests

Cruise Diversey Harbor Aboard a 40' Sea Ray Sundancer in Chicago!

New

Snoozed - Active 12 Oct 2026

Events in Chicago · 10 guests

Tour Chicago On Our Beautiful 31' Sea Ray Sundancer -Accommodate up to 10 Guests

New

Snoozed - Active 02 Aug 2026

Events in Hammond · 10 guests

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

New

Snoozed - Active 14 Jul 2026

Top Destinations Nearby

288
Chicago
Illinois

Illinois Reviews

TH
Tamaria

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
Jason was super communicative and helpful when it came to answering questions I had prior to utilizing the boat. The boat was a great place for me to celebrate the 4th when my friends came in town. I will definitely be booking with him again!
AE
Ahmad

Diversey Harbor 48 ft Luxury Yacht Perfect Play Pen Boat
This is our third time renting a boat from Jason, and once again, we were completely impressed. The entire experience, from the boat itself to the communication, is always top-notch. For this outing, we had Jimmy as our captain, and I cannot recommend him enough! He was fantastic and truly elevated the whole experience for our group. It is always a pleasure dealing with Jason, and we already can't wait to rent from him again!
Alex

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!
Amazing vessel, excellent show up and boat day. Cap was excellent and the boat was amazing. Won’t ever doubt J. Book it.
AP
Alysha

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!
Had an amazing and smooth experience with Jason and our captain! Everything on the listing was accurate and communication was clear.
SB
Sarah

52' Sea Ray Motor Yacht - Largest Boat at Diversey Harbor – Perfect for PlayPen!
Great experience! Communicative host, boat as described, definitely a great value for our money. Would recommend!
Erica

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Ben is wonderful he is so passionate and knowledgeable about sailing and he made it a great time.