We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

Captain
All listings in Chicago

Great sailboat rentals near Chicago, Illinois.

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
$220/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Superowner
$200/hour
37' Luxury Sailing Yacht in Downtown Chicago
Sailing in Chicago · 7 guests

37' Luxury Sailing Yacht in Downtown Chicago

5.0
Superowner
$200+/hour
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+/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
Superowner
$200+/hour
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
$225/hour
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
$225/hour
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+/hour
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
$202/hour
Catamaran Sailing Lessons Chicago
Tours in Chicago · 6 guests

Catamaran Sailing Lessons Chicago

New
Superowner
$350+/hour
40' Sailboat Monroe Harbor Chicago
Sailing in Chicago · 6 guests

40' Sailboat Monroe Harbor Chicago

5.0
$350/hour

Sailing Reviews in Chicago

  1. AD

    Alejandro

    Charter a 31' Pearson Cruising Sloop, Chicago

    Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.

  2. AC

    Alicia

    37' Luxury Sailing Yacht in Downtown Chicago

    When I say I celebrated my 36th birthday on this beautiful boat, it was AMAZING!! Cait was so incredibly helpful and prompt with any questions I had. Her husband Greg was the coolest captain you could possibly meet. I wish I could rate this 10 stars, for it was truly a wonderful experience! You can’t go wrong if you book with them!! Thank you again!!

  3. Alexander

    Alexander

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

    Such a great outing! We went for my girlfriend’s birthday and had the best time. Amazing boat, amazing captain, amazing dog! Could not have gone better.

  4. RM

    Raymond

    37' Luxury Sailing Yacht in Downtown Chicago

    Cait was a lifesaver! Another captain canceled on me less than 40 hours from a booking on a Saturday! The horror of potentially having 10 guest in my crew with that time of letdown was so disappointing. Luckily Cait answered my bat signal and things happen for a reason because we got her amazing sailing yacht and awesome husband, captain Greg, to take care of us which was such a great upgrade! Thank you for taking such good care of us! We will be back and recommending you to all our friends!

  5. PA

    Priyansh

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

    Had a great time on Nijole’s boat. She made our day really special 😊

  6. Hitesh

    Hitesh

    Charter a 31' Pearson Cruising Sloop, Chicago

    Captain Joey was great! Gave very clear directions on how best to meet up with him and is clearly an expert at what he does. Would highly recommend him!