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    4.9
    (28,107 Reviews)

    Page 10 of 10 • 240 listings

    Limited Availability
    Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!
    Events in Chicago · 12 guests

    Enjoy Chicago aboard 45' Sea Ray Express Cruiser Yacht - Perfect for Parties!

    4.9
    Superowner
    Best of 2026
    $400/hour
    Instant Book
    Limited Availability
    Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties
    Events in Chicago · 12 guests

    Enjoy Chicago on this 46' Sea Ray - Great for Birthdays - Bachelorette Parties

    5.0
    Superowner
    Best of 2026
    $400/hour
    Instant Book
    Sleek 51' Luxury Motor Yacht | Parties and Events in Chicago - Fuel Included
    Events in Chicago · 12 guests

    Sleek 51' Luxury Motor Yacht | Parties and Events in Chicago - Fuel Included

    New
    Superowner
    Best of 2026
    $240/hour
    High Demand
    Luxury 35ft Sea Ray Experience in Chicago for Unforgettable Fun
    Events in Chicago · 12 guests

    Luxury 35ft Sea Ray Experience in Chicago for Unforgettable Fun

    4.5
    $550/hour
    Cruise Diversey Harbor Aboard a 40' Sea Ray Sundancer in Chicago!
    Events in Chicago · 13 guests

    Cruise Diversey Harbor Aboard a 40' Sea Ray Sundancer in Chicago!

    New
    Snoozed - Active 12 Oct 2026
    Limited Availability
    35' Luxury Motor Yacht Charter in Chicago with Swim Platform
    Events in Chicago · 12 guests

    35' Luxury Motor Yacht Charter in Chicago with Swim Platform

    4.2
    $180+/hour
    Limited Availability
    40ft Regal Luxury Motor Yacht For 12 People in Chicago (discounted weekday)
    Events in Chicago · 12 guests

    40ft Regal Luxury Motor Yacht For 12 People in Chicago (discounted weekday)

    New
    $275/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
    51ft Sea Ray Sundancer Yacht at Diversey Harbor!
    Events in Chicago · 12 guests

    51ft Sea Ray Sundancer Yacht at Diversey Harbor!

    5.0
    Snoozed - Active 02 Jan 2027
    Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht
    Events in Chicago · 6 guests

    Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht

    5.0
    $375/hour
    High Demand
    40ft Formula 370 Sun Sport Motor Yacht Charter Chicago Playpen Ready
    Events in Chicago · 12 guests

    40ft Formula 370 Sun Sport Motor Yacht Charter Chicago Playpen Ready

    5.0
    $300/hour
    Limited Availability
    Diversey Harbor - 42' Sea Ray Sundancer Luxury Motor Yacht - Fuel Included
    Events in Chicago · 12 guests

    Diversey Harbor - 42' Sea Ray Sundancer Luxury Motor Yacht - Fuel Included

    4.0
    $150/hour
    High Demand
    Ready to Use Doral Alegria 50' Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    Ready to Use Doral Alegria 50' Yacht in Chicago, Illinois

    5.0
    $225/hour
    High Demand
    Charter Sea Ray Sundancer 40’ Motor Yacht In Chicago
    Events in Chicago · 13 guests

    Charter Sea Ray Sundancer 40’ Motor Yacht In Chicago

    4.9
    $200/hour
    Limited Availability
    Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper
    Events in Chicago · 12 guests

    Show-Stopping Lake Michigan Luxury | 36’ Regal LS36 Motor Yacht with Seakeeper

    4.7
    $275+/hour
    Limited Availability
    Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago
    Powerboats in Chicago · 8 guests

    Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago

    5.0
    $248/hour
    Limited Availability
    27ft Sea Ray Sundancer Cruiser on Lake Michigan near Chicago for Up to 8 Guests
    Events in Chicago · 8 guests

    27ft Sea Ray Sundancer Cruiser on Lake Michigan near Chicago for Up to 8 Guests

    5.0
    $160/hour
    Captained 31ft Sports Craft Boat With All the Amenities Down Below
    Events in Chicago · 6 guests

    Captained 31ft Sports Craft Boat With All the Amenities Down Below

    New
    Superowner
    $225/hour
    High Demand
    Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!
    Events in Chicago · 13 guests

    Captained Charter 62' Azimut Luxury Motor Yacht Rental in Chicago!

    5.0
    $1,190/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
    Limited Availability
    Meridian 38 Luxury Yacht Multi-Level Private Charter with Water Toys in Chicago
    Events in Chicago · 13 guests

    Meridian 38 Luxury Yacht Multi-Level Private Charter with Water Toys in Chicago

    4.9
    Superowner
    $250/hour
    Instant Book
    High Demand
    Captained Charter on 60ft Sea Ray Luxury Yacht in Chicago with Captain Sam
    Events in Chicago · 20 guests

    Captained Charter on 60ft Sea Ray Luxury Yacht in Chicago with Captain Sam

    4.8
    $1,500/hour
    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

    New
    $245/hour
    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

    Top Destinations Nearby

    Local Motor Yacht Reviews

    1. HS

      Heather

      Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago

      Carlos was great! He was extremely responsive when the weather looked like it might not be good for a day out on the water. Fortunately, the sun came out and we had the best day. The boat was perfect for our group of 7 and Carlos was a safe and responsible captain.

    2. Ad

      Ashley

      Summertime Chi Vibes - Soak up the Sun in Style! 34' Cruisers South Beach Yacht

      Dan was a legend, so accommodating and kind . He was a part of fam. Cant recommend him enough! Hope to use his boat again!

    3. Amelia

      Amelia

      Diversey Harbor - 42' Sea Ray Sundancer Luxury Motor Yacht - Fuel Included

      Our group had the best time! Paul’s boat was perfect for our group size and he was very responsive leading up to the boat. Thanks Paul!

    4. KA

      Kristina

      Captained Charter on 60ft Sea Ray Luxury Yacht in Chicago with Captain Sam

      We had the best time! The captain and crew were all so nice. Will definitely recommend to anyone looking for a lake day!

    5. NA

      Nikita

      Captained 8 Passengers, 27' Bayliner Ciera Motor Yacht Charter in Chicago

      Carlos is fantastic - super clear directions, boat is great, and we had a fantastic time out in the water today!

    6. Richie

      Richie

      Diversey Harbor - 42' Sea Ray Sundancer Luxury Motor Yacht - Fuel Included

      We had a great time on Paul’s boat for my birthday. The boat had everything we needed and was a really good value. Would book again!

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