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All listings in Chicago

Great sailboat rentals near Chicago, Illinois.

4.9(Average of 558 reviews in this area)
11 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 · 6 guests

37' Luxury Sailboat with Captain in Chicago, Illinois

5.0
Superowner
$280hour
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
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200hour
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
$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

Sailing Reviews in Chicago

  1. 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!

  2. 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.

  3. 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.

  4. 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!

  5. GR
    Gayle
    Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

    We had SUCH a good time on Nijole's boat! We did a sunset/fireworks cruise and it was just the absolute best time, could not recommend it more highly. We were all talking about renting again with Nijole (and her husband and pup Piper) as soon as we got off!

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

    The experience was mesmerising. They were very professional. I booked the slot for 7-9 pm. It was perfect. When we started it was little sunny. We experienced the perfect sunset over the Michigan river seeing the Chicago skyline views. Boat was easy to find. Nicole gave clear instructions for that. I would definitely like to do it again. I highly recommend Harmony for anybody looking for perfect sailing experience.