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All listings in Illinois

Incredible sailboat rentals in Illinois, United States.

Page 1 of 111 listings

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

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

5.0
Superowner
Best of 2023
$220hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200hour
37' Luxury Sailboat with Captain in Chicago, Illinois
Sailing in Chicago · 10 guests

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0
Superowner
$400hour
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor

4.8
$115-$120hour
Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois
Sailing in Chicago · 6 guests

Charter this Beautiful Catalina 36 Sailboat w/Captain in Chicago, Illinois

5.0
$225hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
Superowner
$225hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200hour
38' Sailing Catamaran, Chicago's Largest!
Sailing in Chicago · 12 guests

38' Sailing Catamaran, Chicago's Largest!

5.0
Superowner
$440-$500hour
Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
Sailing in Chicago · 4 guests

Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago

5.0
$202hour
38' Catalina Sailing Cruise in Chicago
Sailing in Chicago · 6 guests

38' Catalina Sailing Cruise in Chicago

5.0
$250hour
40' Sailboat Monroe Harbor Chicago
Sailing in Chicago · 6 guests

40' Sailboat Monroe Harbor Chicago

New
$400hour

Top Destinations Nearby

Sailing Reviews in Illinois

  1. SH

    Susan

    Set Sail with 36' Sailing Boat in Downtown, Chicago

    A wonderful May sail. Great boat for 6 people to relax and enjoy the city skyline, while Ray tends to the sailing. Very competent sailor and friendly.

  2. HW

    Hector

    Set Sail with 36' Sailing Boat in Downtown, Chicago

    Very professional and yet easygoing captain. Boat was very nice - in excellent shape and well maintained. Highly recommend! We will be back again.

  3. vp

    vadim

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

    I want to thank Nijole for her work . Everything was perfectly organized, swimming and sailing. My daughter got seasick and we received full support from the captain. There was also a miracle dog on board ! Dog swam with us and gave us a good mood! Thank you very much! If you want to have a wonderful time sailing, then you are definitely to Nijole! With respect, Vadim Pliss!

  4. AL

    Adam

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

    We loved our experience with Nijole. They took us all around the lake and we loved every minute of it. We even got to swim! They are also a very fun time to hang out with and enjoy the day. Definitely recommend and we will be booking with them multiple times this boating season.

  5. Rachel

    Rachel

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

    Nijole was incredibly helpful, communicative, and kind. She was responsive and went above and beyond to help us reschedule when bad weather struck. We had a lovely trip and she and her husband were delightful to be around! I highly recommend their boat and I can’t wait to sail with them again sometime.

  6. SS

    Sam

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

    I can’t begin to express how kind and courteous our hosts were. They made our trip incredible from the time we stepped on the boat until the time we departed. My friends and I all felt that they went above and beyond to make our experience memorable. If you are looking for a good time on the water look no further and book right here!