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    4.9
    (24,436 Reviews)

    Page 4 of 10 • 240 listings

    High Demand
    Drive It Yourself Or Hire Captain! Affordable Sea Ray Bowrider!
    Powerboats in Chicago · 8 guests

    Drive It Yourself Or Hire Captain! Affordable Sea Ray Bowrider!

    4.8
    Superowner
    Best of 2026
    $150+/hour
    Limited Availability
    50ft Double Deck Yacht "Liquid Asset 3" in Chicago!
    Events in Chicago · 13 guests

    50ft Double Deck Yacht "Liquid Asset 3" in Chicago!

    5.0
    Superowner
    Best of 2026
    $300/hour
    Limited Availability
    Summertime Chi Ready! Rent this Carver 38 Santego Motor Yacht for 12 Guests
    Events in Chicago · 12 guests

    Summertime Chi Ready! Rent this Carver 38 Santego Motor Yacht for 12 Guests

    5.0
    $325/hour
    High Demand
    New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago
    Events in Chicago · 12 guests

    New Spacious 40ft Cruisers Motor Yacht for Rent in Chicago

    5.0
    Superowner
    $400/hour
    Limited Availability
    Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago
    Events in Chicago · 8 guests

    Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

    4.8
    $300/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
    Limited Availability
    Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!
    Events in Chicago · 12 guests

    Luxurious, Spacious, Clean 40' Cruiser's Yacht (Super Owner) in Chicago, IL!!

    5.0
    Superowner
    $300+/hour
    Luxury 54' Sea Ray Sundancer Yacht for Charter in Chicago
    Events in Chicago · 12 guests

    Luxury 54' Sea Ray Sundancer Yacht for Charter in Chicago

    5.0
    $500/hour
    Limited Availability
    Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht
    Powerboats in Chicago · 12 guests

    Luxury Cruising on Lake Michigan aboard 32' Chaparral Signature Yacht

    4.7
    Superowner
    $350/hour
    Limited Availability
    Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!
    Events in Chicago · 12 guests

    Chicago Summer In Style - 33' Monterey 302 Yacht for Charter on Lake Michigan!

    4.9
    $250/hour
    Limited Availability
    63ft Premier Sea Ray Sundancer Yacht Perfect for Chicago Playpen, River, Winery
    Events in Chicago · 12 guests

    63ft Premier Sea Ray Sundancer Yacht Perfect for Chicago Playpen, River, Winery

    5.0
    Superowner
    $700/hour
    40' Cruisers Yachts "Bad Boys II" for rent in Chicago
    Events in Chicago · 13 guests

    40' Cruisers Yachts "Bad Boys II" for rent in Chicago

    New
    $818/hour
    Limited Availability
    "Excelling in Excellence" 46' Azimut Yacht Charter in Chicago, IL
    Events in Chicago · 13 guests

    "Excelling in Excellence" 46' Azimut Yacht Charter in Chicago, IL

    New
    $772/hour
    Limited Availability
    Classic 43' Hatteras with Captain included in Chicago
    Events in Chicago · 6 guests

    Classic 43' Hatteras with Captain included in Chicago

    New
    $300+/hour
    Limited Availability
    39' Sea Ray Sundancer for 11 Guests – 3 Boats! Weekday Discount!
    Events in Chicago · 11 guests

    39' Sea Ray Sundancer for 11 Guests – 3 Boats! Weekday Discount!

    5.0
    $425/hour
    34' Luxury Sea Ray Sundancer Yacht in Excellent condition for rent in Chicago
    Events in Chicago · 12 guests

    34' Luxury Sea Ray Sundancer Yacht in Excellent condition for rent in Chicago

    New
    $275/hour
    Limited Availability
    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
    Limited Availability
    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
    Limited Availability
    36ft Luxury Silverton Motor Yacht in Chicago - 12 Guests Can Relax and Have Fun
    Events in Chicago · 12 guests

    36ft Luxury Silverton Motor Yacht in Chicago - 12 Guests Can Relax and Have Fun

    New
    Snoozed - Active 10 Sep 2026
    Limited Availability
    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL
    Events in Chicago · 13 guests

    45' Cruiser Yacht "MoEz Chilli'n" Chicago, IL

    New
    $1,089/hour
    Limited Availability
    Charter a 40' Luxury Beneteau Gran Tursimo Yacht - 11 Guests, 3 Boats Available!
    Events in Chicago · 11 guests

    Charter a 40' Luxury Beneteau Gran Tursimo Yacht - 11 Guests, 3 Boats Available!

    4.8
    $500/hour
    Limited Availability
    41ft Sea Ray Sundancer 410 Yacht in Chicago, Illinois - Stunning Throughout
    Events in Chicago · 13 guests

    41ft Sea Ray Sundancer 410 Yacht in Chicago, Illinois - Stunning Throughout

    5.0
    $500/hour
    High Demand
    'Genius' 40ft Sea Ray Sundancer Captained Charter With All Amenities In Chicago!
    Events in Chicago · 13 guests

    'Genius' 40ft Sea Ray Sundancer Captained Charter With All Amenities In Chicago!

    5.0
    Superowner
    $275/hour
    Limited Availability
    Luxury 40' Sea Ray Sundancer Motor Yacht with Premium Sound System in Chicago
    Events in Chicago · 12 guests

    Luxury 40' Sea Ray Sundancer Motor Yacht with Premium Sound System in Chicago

    5.0
    $300/hour

    Top Destinations Nearby

    Local Tours Reviews

    1. AP

      Ashley

      Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

      Great experience. From the moment I submitted my request for the boat, extremely fast communication. Very much appreciate all the great communication and timeliness. The actual boat ride was so fun, and it flowed so well- from the morning of, when i got a text from the captain about where to meet, to getting on the water. Great experience.

    2. PT

      Peter Michael

      Drive It Yourself Or Hire Captain! Affordable Sea Ray Bowrider!

      We had a great time out on the lake. Communication with Chris was easy and quick qhich made the experience so easy. I would definitely reach out to Chris again when in Chicago.

    3. LK

      Lance

      Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

      We had a great trip with Shaun aboard the “All In.” Gorgeous weather day was an added bonus! Highly recommend!

    4. Michael

      Michael

      50ft Double Deck Yacht "Liquid Asset 3" in Chicago!

      Fantastic! I have used Chris’ fleet multiple times now. They’re pros. They make everything fun and approachable. The vessels are great and you get what’s advertised.

    5. KD

      Kate

      'Genius' 40ft Sea Ray Sundancer Captained Charter With All Amenities In Chicago!

      Danyelle was such an amazing host! the boat was clean and had everything we needed. We had the best day!

    6. MP

      Megan

      Come enjoy fun in the sun on our 30ft Bayliner Ciera for 8 passengers in Chicago

      We had an amazing time. Dock location was convenient. Overall great experience. Will recommend

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