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    All listings in Illinois

    Incredible sailboat rentals in Illinois, United States.

    5.0(Average of 582 reviews in this area)•
    Boat Rentals,United States,Illinois
    24 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 2022
    $220hour
    37' Luxury Sailboat with Captain in Chicago, Illinois
    Sailing in Chicago · 6 guests

    37' Luxury Sailboat with Captain in Chicago, Illinois

    5.0
    Superowner
    $300hour
    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
    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
    Best of 2022
    $300hour
    Charter this Beautiful Catalina 36 Sailboat w/Professional in Chicago, Illinois
    Sailing in Chicago · 6 guests

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

    5.0
    $225hour
    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

    4.9
    $100hour
    $550 per hour 13ppl!
    Sailing in Chicago · 13 guests

    $550 per hour 13ppl!

    5.0
    Best of 2022
    $550hour
    Maxum Yacht - Huge open seating area & bow sunpads! Discounted Rates thru early June
    Events in Chicago · 12 guests

    Maxum Yacht - Huge open seating area & bow sunpads! Discounted Rates thru early June

    5.0
    Superowner
    Best of 2022
    $300hour
    Instant Book
    46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests
    Events in Chicago · 12 guests

    46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests

    5.0
    Best of 2022
    $220hour
    Instant Book
    Charter a 31' Pearson Cruising Sloop, Chicago
    Sailing in Chicago · 6 guests

    Charter a 31' Pearson Cruising Sloop, Chicago

    4.4
    Superowner
    $200hour
    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
    Super Spacious Silverton Express Cruiser in Chicago, Illinois
    Events in Chicago · 12 guests

    Super Spacious Silverton Express Cruiser in Chicago, Illinois

    5.0
    Superowner
    $350hour
    Early Summer Specials for 2023!
    Events in Chicago · 10 guests

    Early Summer Specials for 2023!

    5.0
    $185hour
    Instant Book
    38' Sailing Catamaran, Chicago's Largest!
    Sailing in Chicago · 12 guests

    38' Sailing Catamaran, Chicago's Largest!

    5.0
    Superowner
    $500hour
    Sailing Catamaran along Chicago's Lakefront 6ppl
    Sailing in Chicago · 6 guests

    Sailing Catamaran along Chicago's Lakefront 6ppl

    5.0
    Best of 2022
    $450hour
    38' Catalina Sailing Cruise in Chicago
    Sailing in Chicago · 6 guests

    38' Catalina Sailing Cruise in Chicago

    5.0
    $250hour
    Learn Kiteboarding in Chicago, Illinois
    Adventures in Chicago · 1 guest

    Learn Kiteboarding in Chicago, Illinois

    5.0
    $120hour
    37’ Rinker Yacht - AFFORDABLE and GREAT for Parties up to 12 guests (KMB #12)
    Events in Chicago · 12 guests

    37’ Rinker Yacht - AFFORDABLE and GREAT for Parties up to 12 guests (KMB #12)

    New
    Superowner
    $250hour
    Multi Level 38' Carver Yacht for 12 Guests in Chicago, IL - Best Value! (MPY#6)
    Events in Chicago · 12 guests

    Multi Level 38' Carver Yacht for 12 Guests in Chicago, IL - Best Value! (MPY#6)

    New
    Superowner
    Best of 2022
    $400hour
    43' Tiara Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    43' Tiara Motor Yacht Rental in Chicago, Illinois

    New
    $550hour
    Sail Aboard 148' Tall Ship Windy - The Official Ambassador of the City of Chicago - 1pm Daily ONLY
    Tours in Chicago · 150 guests

    Sail Aboard 148' Tall Ship Windy - The Official Ambassador of the City of Chicago - 1pm Daily ONLY

    New
    $42person
    410 Sundancer Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    410 Sundancer Motor Yacht Rental in Chicago, Illinois

    New
    $500hour
    Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois
    Events in Chicago · 12 guests

    Sea Ray 370 Sundancer Motor Yacht Rental in Chicago, Illinois

    New
    $300hour
    40' Luxury Cruiser/Racer Sailboat with Captain Monroe Harbor Chicago
    Sailing in Chicago · 6 guests

    40' Luxury Cruiser/Racer Sailboat with Captain Monroe Harbor Chicago

    New
    $400hour

    Top Destinations Nearby

    Sailing Reviews in Illinois

    1. VM
      Varun
      Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

      First time in a sailboat and it was a good time!

    2. nk
      neil
      46' Beautiful Sea Ray Yacht - Perfect for Parties - 12 Guests

      Great experience, would recommend and will definitely book again!

    3. 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!

    4. 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!

    5. 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.

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

      Very happy with our booking! The weather was looking iffy and Nijole was super accommodating shifting the time to allow for better weather. The boat ride was super fun and they took us around on the lake. They took care of everything and we didn’t have to worry about anything just enjoy !

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