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    Lake Michigan, US Boat Rentals & Yacht Charters

    4.9
    (6,644 Reviews)

    Page 7 of 15 • 353 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    New Boat in Chicago! 55ft Sea Ray Sundancer, Sleek & Spacious
    Events in Chicago · 13 guests

    New Boat in Chicago! 55ft Sea Ray Sundancer, Sleek & Spacious

    New
    Superowner
    Best of 2026
    $450/hour
    Limited Availability
    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
    Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour
    Powerboats in Chicago · 14 guests

    Chicago Private Party Boat - 14 Passenger Captained Events & Playpen Tour

    5.0
    Superowner
    Best of 2026
    $600/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
    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
    High Demand
    Sea Ray 400 Express Cruiser Yacht Available In Chicago
    Events in Chicago · 12 guests

    Sea Ray 400 Express Cruiser Yacht Available In Chicago

    5.0
    $250/hour
    High Demand
    50ft ITALIAN YACHT - ELEGANT DESIGN - LUXURY VIBES - ONLY ONE LIKE THIS IN CHI
    Events in Chicago · 13 guests

    50ft ITALIAN YACHT - ELEGANT DESIGN - LUXURY VIBES - ONLY ONE LIKE THIS IN CHI

    5.0
    $400/hour
    Premium Power Boat Rental - Glastron 205
    Powerboats in Michigan · 11 guests

    Premium Power Boat Rental - Glastron 205

    5.0
    $125/hour
    Limited Availability
    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago
    Events in Chicago · 12 guests

    Soak Up the Sun Onboard a 42' Sea Ray Express Cruiser in Chicago

    5.0
    $275/hour
    Limited Availability
    2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois
    Events in Chicago · 12 guests

    2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

    4.7
    $400/hour
    35ft Center Console for daytime cruises, big lake fishing and weekend adventures
    Powerboats in Holland · 6 guests

    35ft Center Console for daytime cruises, big lake fishing and weekend adventures

    5.0
    $150/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
    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
    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
    Limited Availability
    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests
    Events in Chicago · 12 guests

    Chicago Private Yacht Charter Experience on 54’ Neptunus Express - 12 Guests

    5.0
    $300/hour
    Limited Availability
    Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests
    Powerboats in Chicago · 13 guests

    Double Decker 50ft Sea Ray Flybridge Yacht in Chicago - 13 Guests

    5.0
    Superowner
    Best of 2026
    $300+/hour
    Limited Availability
    44ft Azimut Premier Party Yacht Chicago for Up to 13 - plus Jet Ski Available
    Events in Chicago · 13 guests

    44ft Azimut Premier Party Yacht Chicago for Up to 13 - plus Jet Ski Available

    5.0
    Superowner
    $670+/hour
    Explore and Enjoy Glen Lake with 2550 RL Bennington Pontoon Boat
    Powerboats in Michigan · 13 guests

    Explore and Enjoy Glen Lake with 2550 RL Bennington Pontoon Boat

    5.0
    $75+/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
    High Demand
    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 with 36' Sailing Boat in Downtown, Chicago for 6 Guests
    Sailing in Chicago · 6 guests

    Set Sail with 36' Sailing Boat in Downtown, Chicago for 6 Guests

    5.0
    $225/hour
    Limited Availability
    Stunning 45’ Sea Ray Sundancer Motor Yacht In Chicago
    Events in Chicago · 12 guests

    Stunning 45’ Sea Ray Sundancer Motor Yacht In Chicago

    5.0
    Superowner
    Best of 2026
    $350/hour
    Instant Book

    Top Destinations Nearby

    Lake Michigan Reviews

    1. Patrick

      Patrick

      50ft ITALIAN YACHT - ELEGANT DESIGN - LUXURY VIBES - ONLY ONE LIKE THIS IN CHI

      Paul and Seba were excellent hosts. The boat was clean, ready to go on time, and exceptionally flexible when we were a little bit late. Additionally they had great suggestions on where to go and how to spend time on the water. We plan to book with them again before the end of the year!

    2. KR

      Kelsey

      Sea Ray 400 Express Cruiser Yacht Available In Chicago

      Lovie’s boat was so much fun! It fit our group of 11 so effortlessly. The sound system bumped, and the floaty they provided was perfect. We had such a good time! Would definitely book this boat again!

    3. KH

      Karen

      Stunning 45’ Sea Ray Sundancer Motor Yacht In Chicago

      Book this trip! We had an amazing day out on the lake. The boat was SO NICE, Captain Peter and Dorothy were WONDERFUL and booking with Eugene was great. I HIGHLY recommend and plan to use them again.

    4. AR

      Alejandra

      Sea Ray 400 Express Cruiser Yacht Available In Chicago

      Lovie was great! She communicated well and the experience wad amazing!

    5. TV

      Toni

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

      Great boat & crew. We all had a fantastic time and look forward to going again soon!

    6. IF

      Ian

      2020 Beneteau GT 42' "James Bond" Yacht in Chicago, Illinois

      Super smooth experience. Captain John was fantastic. Would recommend to anyone!

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