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    Chicago, Illinois Boat Rentals & Yacht Charters

    4.9
    (5,996 Reviews)

    Page 8 of 12 • 271 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago
    Sailing in Chicago · 12 guests

    No tie-ups: 39' Catalina Sailboat with Huge Cockpit in Chicago

    4.8
    $245/hour
    50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package
    Powerboats in Chicago · 36 guests

    50ft Skipperliner Tiki Pontoon Cruise in Chicago with Beverage Package

    4.6
    $1,350/hour
    Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience
    Events in Chicago · 12 guests

    Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience

    5.0
    $350/hour
    49 Passengers 57' Power Catamaran - Perfect For Events in Chicago
    Events in Chicago · 49 guests

    49 Passengers 57' Power Catamaran - Perfect For Events in Chicago

    5.0
    Superowner
    $1,000/hour
    Regal 26 FasDeck for Chicago Charters, Play Pen, River Tours and Cruising
    Powerboats in Chicago · 6 guests

    Regal 26 FasDeck for Chicago Charters, Play Pen, River Tours and Cruising

    5.0
    $300/hour
    44’ Regal Yacht | Diversey Harbor | Free Fuel, Champagne & Two Floating Islands
    Events in Chicago · 13 guests

    44’ Regal Yacht | Diversey Harbor | Free Fuel, Champagne & Two Floating Islands

    5.0
    $300/hour
    Premium 42' Meridian Flybridge Yacht Charter In Chicago - Lake Michigan
    Events in Chicago · 12 guests

    Premium 42' Meridian Flybridge Yacht Charter In Chicago - Lake Michigan

    5.0
    $500/hour
    Beautiful 42ft Sea Ray Express Spacious Yacht In Chicago
    Powerboats in Chicago · 13 guests

    Beautiful 42ft Sea Ray Express Spacious Yacht In Chicago

    New
    $200/hour
    Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!
    Events in Chicago · 10 guests

    Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!

    5.0
    $300+/hour
    31ft Sea Ray 310 Sedan Bridge Motor Yacht Private Full Day Charter - Chicago, IL
    Events in Chicago · 12 guests

    31ft Sea Ray 310 Sedan Bridge Motor Yacht Private Full Day Charter - Chicago, IL

    3.5
    $300/hour
    Learn Kiteboarding in Chicago with Professional Kiteboard Instructor
    Adventures in Chicago · 1 guest

    Learn Kiteboarding in Chicago with Professional Kiteboard Instructor

    5.0
    $185/hour
    1962 Chris Craft Yacht Charter on the Chicago River!
    Events in Chicago · 6 guests

    1962 Chris Craft Yacht Charter on the Chicago River!

    5.0
    $250+/hour
    36' Wellcraft Grand Sport Yacht for Intimate Gatherings and Events in Chicago
    Events in Chicago · 12 guests

    36' Wellcraft Grand Sport Yacht for Intimate Gatherings and Events in Chicago

    5.0
    $250/hour
    32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests
    Events in Chicago · 6 guests

    32ft SeaRay Sundancer Motor Yacht for Charter in Chicago for 6 Guests

    5.0
    $300/hour
    Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”
    Sailing in Chicago · 10 guests

    Private Cruise on 40’ Luxury Sailing Yacht - Beneteau Oceanis 393 “Vagabond”

    5.0
    $275/hour
    Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht
    Events in Chicago · 10 guests

    Set Sail in Downtown Chicago with Beautiful 35ft Cruiser Motor Yacht

    5.0
    $275/hour
    No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor
    Events in Chicago · 13 guests

    No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor

    5.0
    $250/hour
    Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago
    Events in Chicago · 12 guests

    Private 44ft Cruiser 4450 Express Yacht Experience on Lake Michigan – Chicago

    5.0
    $325/hour
    Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!
    Events in Chicago · 120 guests

    Tiki-Chic Yacht, 40-120 Passengers, One deck option. Beverage package included!

    5.0
    $1,500/hour
    50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina
    Events in Chicago · 24 guests

    50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina

    5.0
    $1,136/hour
    Party Cruise on 40ft Sea Ray Express Yacht Chicago for You & 12 Friends
    Events in Chicago · 12 guests

    Party Cruise on 40ft Sea Ray Express Yacht Chicago for You & 12 Friends

    5.0
    $300+/hour
    40' Regal Commandore Luxury Cruiser in Chicago
    Events in Chicago · 12 guests

    40' Regal Commandore Luxury Cruiser in Chicago

    5.0
    $300/hour
    Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises
    Events in Chicago · 13 guests

    Chicago: 52' Cruisers Express Luxury Yacht for Private Lake Michigan Cruises

    5.0
    $750/hour
    37ft Cruiser Express Motor Yacht Charter Chicago Plus Jet Ski Included
    Events in Chicago · 12 guests

    37ft Cruiser Express Motor Yacht Charter Chicago Plus Jet Ski Included

    5.0
    $350/hour

    Top Destinations Nearby

    Chicago Reviews

    1. MO

      Maddy

      No Tie Ups - 40ft Sea Ray Yacht lots of room for 13 at DuSable Harbor

      Great rental! Martin was very communicative, loved that the pricing was all inclusive of the tip. Boat was large, complimentary floaties and lilypad included. Highly recommend

    2. Jet

      Jet

      50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina

      We rented this boat for my bachelorette and it was amazing! The crew was awesome and the boat was perfect for what we needed. Highly recommend and would rent again!

    3. Cardisha

      Cardisha

      Luxurious 47' Sea Ray Sun Yacht - Explore Lake Michigan the Ultimate Experience

      Breanna is amazing!! Any time I’m in Chicago, I know whose vessel to book! Shoutout to Capt Mike too, lovely experience with even lovelier people :)

    4. AC

      Alexandria

      Regal 26 FasDeck for Chicago Charters, Play Pen, River Tours and Cruising

      10/10 experience. Captain was communicative the whole trip, the boat was clean and beautiful. He kept up safe and allowed us to have our fun. The respect was mutual. Thanks Captain!

    5. DD

      David

      50' Corinthian Big Party Boat for up to 24 people at Navy Pier Marina

      Incredible professional. Would highly recommend. 10/10

    6. LT

      Loi

      Awesome Deal! | Cruise Chicago in Style on a 40' Beneteau Grand Turismo Yacht!

      Awesome time with Alonzo, the boat was very nice and was a smooth experience. Would recommend booking anytime if you have a group!

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