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    All listings in Chicago

    Search yacht rentals in Chicago, Illinois.

    4.9
    (4,367 Reviews)

    Page 5 of 10 • 232 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    45ft Sea Ray Sundancer Motor Yacht Pure Comfort in Chicago!
    Events in Chicago · 10 guests

    45ft Sea Ray Sundancer Motor Yacht Pure Comfort in Chicago!

    5.0
    $300/hour
    Limited Availability
    Set Sail on a Spacious 42' Silverton Express Cruiser Yacht
    Powerboats in Chicago · 12 guests

    Set Sail on a Spacious 42' Silverton Express Cruiser Yacht

    5.0
    $275/hour
    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

    New
    $248/hour
    High Demand
    Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible SoundSystem!
    Events in Chicago · 12 guests

    Clean 40' Sea Ray Motor Yacht With Plenty of Room and Incredible SoundSystem!

    5.0
    $350/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
    Limited Availability
    Maxum 44ft Motor Yacht "My Kinda Party"
    Powerboats in Chicago · 13 guests

    Maxum 44ft Motor Yacht "My Kinda Party"

    4.9
    Superowner
    Best of 2026
    $260+/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
    Limited Availability
    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina
    Events in Chicago · 13 guests

    45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

    5.0
    $300/hour
    Limited Availability
    SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests
    Events in Chicago · 12 guests

    SeaRay 330 Motor Yacht Charter in Chicago, Illinois for 12 Guests

    5.0
    $200/hour
    41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago
    Events in Chicago · 12 guests

    41ft Sea Ray Sundancer Motor Yacht Lake Michigan Charter from Chicago

    5.0
    Superowner
    Best of 2026
    $375+/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
    55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand
    Events in Chicago · 12 guests

    55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

    5.0
    $375+/hour
    Limited Availability
    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)
    Events in Chicago · 12 guests

    38ft Sea Ray Sundancer in Chicago, Burhnam Harbor (Up to 12 guests)

    5.0
    Superowner
    $250/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
    Limited Availability
    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
    Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago
    Events in Chicago · 13 guests

    Stunning Multi-Level 47’ Carver Yacht for Summertime in Chicago

    4.8
    $300/hour
    High Demand
    Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago
    Events in Chicago · 13 guests

    Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago

    4.8
    Superowner
    $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
    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
    Limited Availability
    Sea Ray 48' Motor Yacht in Chicago Playpen, River, Winery, Lilly Pad
    Events in Chicago · 12 guests

    Sea Ray 48' Motor Yacht in Chicago Playpen, River, Winery, Lilly Pad

    5.0
    Superowner
    $375+/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
    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
    Limited Availability
    Chicago 40ft Formula Performance Cruiser for Up to 13 Guests
    Events in Chicago · 13 guests

    Chicago 40ft Formula Performance Cruiser for Up to 13 Guests

    5.0
    $349/hour

    Top Destinations Nearby

    Motor Yacht Reviews in Chicago

    1. LP

      Lijana

      55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

      We rented this boat for our 30th anniversary and it was better than we hoped! How lucky we were to find Robert B. His boat is beautiful, very clean, perfect for the party of 12 people. And he was so nice to give us the parking pass to be dropped right next to the boat. Thank you so much! We highly recommend this vessel to anybody who wants to have a great time! Lijana and Peter Paulettti ❤️❤️❤️

    2. BH

      Benjamin

      55' Sea Ray 510 Sundancer Luxury Yacht in Chicago with Captain and Deckhand

      Robert was friendly and communicative. He put me in touch with a captain (Jamie) who added to the experience. Great boat. No complaints.

    3. 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!

    4. Cindy

      Cindy

      Maxum 44ft Motor Yacht "My Kinda Party"

      Had an amazing birthday weekend with my friends for my birthday, Captin Drake was great and I would definitely book again! Thank you for an amazing experience.

    5. CF

      Connie

      45' Formula 400 Super Sport Luxury Yacht Charter at Navy Pier Marina

      Look no further for your boat rental needs. Captain Douglas will help you choose the perfect boat and crew to make your experience beyond what you can imagine!!

    6. MS

      Milap

      Gorgeous 61’ Sunseeker Predator Motor Yacht with Floating island in Chicago

      Exactly as described, great operation, great captains, smooth as butter!

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