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    4.9
    (23,336 Reviews)

    Page 4 of 10 • 240 listings

    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
    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion
    Events in Chicago · 12 guests

    42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

    5.0
    $250/hour
    Limited Availability
    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
    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
    High Demand
    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
    Limited Availability
    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
    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
    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

    4.9
    Superowner
    $300/hour
    High Demand
    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
    "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
    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
    Beautiful 37' Sea Ray Sundancer Perfect for Any Occasion In Chicago
    Events in Chicago · 12 guests

    Beautiful 37' Sea Ray Sundancer Perfect for Any Occasion In Chicago

    New
    $300/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
    $350+/hour
    Limited Availability
    Cruise Lake Michigan Aboard 40ft Sea Ray Luxury Yacht
    Events in Chicago · 12 guests

    Cruise Lake Michigan Aboard 40ft Sea Ray Luxury Yacht

    New
    $300/hour
    High Demand
    34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!
    Events in Chicago · 12 guests

    34' Chris-Craft Yacht for Lakefront Fun! Music Lights and a Great time!!!

    New
    $300/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
    $200/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
    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
    $200/hour
    Gorgeous 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing in Chicago
    Events in Chicago · 12 guests

    Gorgeous 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing in Chicago

    5.0
    $500/hour
    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
    $275/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. Andre

      Andre

      Gorgeous 54' Sea Ray Sundancer w/ Huge Cockpit for Parties & Dancing in Chicago

      Lashawn and her crew are an experience like no other. You get persons who are attentive, Supportive and likeminded as it relates to one’s needs and likeness. An amazing team of professionals that seeks to offer the best in customer services and responsiveness. X

    3. CF

      Colleen

      42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

      We had the best time! The boat was beautiful, everything was super clean, and the crew was so friendly and helpful. They made the whole experience easy and fun. We would 100% book again. 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. MF

      Madalyn

      42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

      I had a great experience and we had an absolutely beautiful time for my sister‘s bachelorette! The captain was great!

    6. AL

      Anneliese

      42ft Trojan Party Yacht Chicago for 12 Guests Every Occasion

      We had the best time on the boat! Just as advertised and our captain was great.

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