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  • What Is a Mailboat? Working Postal Routes You Can Ride in 2026
  • Best results for

    Yacht Charters in Wood Dale, IL

    Showing 1-24 of 69 results
    Cruise Lake Michigan in Chicago With a Licensed Captain

    Cruise Lake Michigan in Chicago With a Licensed Captain

    Hire a US Coast Guard licensed captain for your Chicago boat day

    4.9 • 1K reviews
    $289/ person
    Private 43' Luxury Yacht Charter in Chicago

    Private 43' Luxury Yacht Charter in Chicago

    Spread out with a spacious cockpit and two private staterooms

    $590/ boat
    Chicago 36' Yacht Charter

    Chicago 36' Yacht Charter

    Relax together with a flybridge lounge, wide walkways, and onboard music

    $1,696
    Chicago Private Yacht Charter

    Chicago Private Yacht Charter

    Set your own pace on a private Chicago yacht cruise

    $1,537& up
    Chicago 42' Power Catamaran Charter

    Chicago 42' Power Catamaran Charter

    Double-decker catamaran for private entertaining and water views

    $3,180
    Private 47' Yacht Charter in Chicago

    Private 47' Yacht Charter in Chicago

    Cruise Chicago by private 47 ft yacht with space for up to 12 guests

    4.6 • 122 reviews
    $2,120
    Chicago River Cruise by Diversey Harbor

    Chicago River Cruise by Diversey Harbor

    Cruise the Chicago River for skyline views and Riverwalk sights

    5.0 • 273 reviews
    $1,431& up
    Chicago 56' Yacht Charter

    Chicago 56' Yacht Charter

    Private yachting for celebrations, family gatherings, and corporate outings

    4.9 • 1K reviews
    $1,552& up
    Boat Charter to Chicago Playpen

    Boat Charter to Chicago Playpen

    Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

    5.0 • 58 reviews
    $239/ boat
    Private Yacht Charter From Navy Pier

    Private Yacht Charter From Navy Pier

    Cruise Chicago’s waterfront with a professional crew and private gathering spaces

    5.0 • 37 reviews
    $2,760& up
    Chicago 47' Yacht Charter

    Chicago 47' Yacht Charter

    Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

    5.0 • 23 reviews
    $1,272& up
    Cruise Chicago on a 40' Private Yacht Charter

    Cruise Chicago on a 40' Private Yacht Charter

    Private 40' Sea Ray yacht rental in Chicago for up to 13

    5.0 • 1 reviews
    $961& up
    Wilmette 51' Sea Ray Charter

    Wilmette 51' Sea Ray Charter

    Cruise and swim aboard a spacious Sea Ray with room to lounge

    4.4 • 55 reviews
    $1,675& up
    Cruise Chicago on a Private Yacht Charter

    Cruise Chicago on a Private Yacht Charter

    Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

    4.3 • 28 reviews
    $1,643& up
    Cruise Lake Michigan From Chicago on a Day Charter

    Cruise Lake Michigan From Chicago on a Day Charter

    Sail Lake Michigan on a private day charter with skyline views

    5.0 • 273 reviews
    $954& up
    Chicago 4-Hour Captain for Hire

    Chicago 4-Hour Captain for Hire

    Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises

    4.9 • 1K reviews
    $428
    Private Chicago Skyline Yacht Charter from Navy Pier

    Private Chicago Skyline Yacht Charter from Navy Pier

    Celebrate on the Gypsy Spirit along Chicago’s waterfront

    5.0 • 37 reviews
    $2,990& up
    Private 50' Sea Ray Yacht Charter in Chicago

    Private 50' Sea Ray Yacht Charter in Chicago

    Set the mood on board with your own food, drinks and music

    5.0 • 23 reviews
    $1,696/ boat
    Chicago Fireworks Cruise

    Chicago Fireworks Cruise

    Watch Navy Pier fireworks from a private yacht

    5.0 • 273 reviews
    $1,113& up
    4-Hour Boat Charter in Chicago

    4-Hour Boat Charter in Chicago

    Bring your group aboard for a captain-led Chicago outing

    4.9 • 1K reviews
    $428
    Private 40' Motor Yacht Rental in Chicago

    Private 40' Motor Yacht Rental in Chicago

    Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

    5.0 • 1 reviews
    $961& up
    50' Yacht Charter in Chicago

    50' Yacht Charter in Chicago

    Cruise Lake Michigan with a full kitchen, two bathrooms, and skyline views

    4.3 • 28 reviews
    $1,864& up
    Yacht Charter in Chicago Aboard a 47' Carver

    Yacht Charter in Chicago Aboard a 47' Carver

    Cruise a 47-foot Carver with space to relax, dine, and play your music

    5.0 • 23 reviews
    $1,696& up
    Private 38' Motor Yacht Charter in Chicago

    Private 38' Motor Yacht Charter in Chicago

    Charter a private 38' yacht on Lake Michigan for up to 13 guests

    5.0 • 1 reviews
    $1,223& up
    123
    Wood Dale Things To Do
    Yacht ChartersBoat Tours22Sailing18Kayaking Tours16Architectural Tours13
    More
    • Art Tours12
    • Food Tours12
    • Birthday Packages11
    • Boat Rentals8
    • City Tours8
    • Bike Tours6
    • Dessert Tours6
    Themed Experiences
    6
  • Pizza Tours5
  • Bike Rentals4
  • Escape Games4
  • Helicopter Tours4
  • Historical Tours4
  • Jet Skiing4
  • Museum Tours4
  • Seasonal and Holiday4
  • Yoga4
  • Baking Classes3
  • Car Rentals3
  • Celebrations3