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Group Size (2)
All listings in Illinois

Incredible sailboat rentals in Illinois, United States.

Page 1 of 113 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
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

New
Superowner
$175-$250hour
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 Sailing Yacht in Downtown Chicago
Sailing in Chicago · 10 guests

37' Luxury Sailing Yacht in Downtown Chicago

5.0
Superowner
$200-$300hour
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
Chicago's Largest Chartered Catamaran!
Sailing in Chicago · 13 guests

Chicago's Largest Chartered Catamaran!

5.0
Superowner
$375-$600hour
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
Catamaran Sailing Lessons Chicago
Tours in Chicago · 6 guests

Catamaran Sailing Lessons Chicago

New
Superowner
$350-$450hour
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
$350hour

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Sailing Reviews in Illinois

  1. dr

    david

    Set Sail with 36' Sailing Boat in Downtown, Chicago

    Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.

  2. Arina

    Arina

    37' Luxury Sailing Yacht in Downtown Chicago

    We rented Greg’s yacht to celebrate my birthday and it was truly amazing!! The yacht itself was very clean and beautiful and Greg was accommodative and helping us with any requests we had. Thank you!

  3. MM

    Mandy

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

    Nijole was great, we had a great 2 hours sailing and got wonderful views of the skyline! She was very responsive and flexible as well when we had to change our departure time due to rain.

  4. JT

    Joyce

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

    This was a beautiful day filled with champagne, non-stop music, great food and family. Captain Nijole was a gracious and fun host.

  5. 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.

  6. 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.