Chicago Sailing with a Sailo Boat Charter

Explore Lake Michigan from Chicago, sailing with a private yacht rental

Renting a boat charter in Chicago is one of the best things to do in the summer months, whether you’re planning to party or just to escape the city heat. Find your perfect private boat rental with Sailo!

Despite being a long way from the sea, Chicago offers lots of things to do out on the water. From helming a sailboat, going on a fishing trip or enjoying the wild parties of the summer months, there is always something going on. When it comes to choosing your ideal yacht, Sailo offer the perfect selection of boat charters in Chicago for adventure boat trips, bachelor or bachelorette parties, or big events like weddings or corporate meetings.

 

Sailing the Windy City

Feeling the wind in the sails of your Chicago boat charter out on Lake Michigan is one of the best ways to take in the awe inspiring views of the Windy City. The lake makes a great playground, especially in the summer months, with plenty of coastline to explore. 

Just a short boat ride from downtown Chicago there is a whole world of fishing towns and beaches. Sure, you could drive there, but the adventure and thrill of sailing is something special which can really make a big difference to your vacation. Most people rent a yacht charter from Chicago for a day trip, but there is always the option for something longer if you would like to explore.

 

Partying in Chi-Town

Chicago likes to party, and one of the most wild parties is the Chicago Scene Boat Party. Hundreds of boats and thousands of attendees arrive at the Playpen, an area just off the shore of the downtown area. People from all walks of life come to enjoy a day on the deck of their yacht and party like there's no tomorrow.

All year round, of course, there are also plenty of opportunities to party on the water. You’ll find Sailo offers a great selection of party boats in Chicago which are perfect for big or small groups. Whatever the occasion, from weddings or corporate events to a wild weekend of partying, take a look at our selection of great motor yachts and sailboats on the shores of Lake Michigan.

City Winery on the River Walk

31st Harbour

Marina

Belmont Harbour

Burnham Harbour

Burnham Harbour

Chicago Monroe Harbor

The Chicago Yacht Club Race to Mackinac

chicago-sailing-sailo-boat-rental-races

Every year the Chicago Yacht Club hosts this prestigious race across Lake Michigan to Mackinac in Lake Huron. Although you might not want to take your yacht charter on the race, finding your own boat rental for the day is a great way to enjoy Chicago sailing as part of the action. From the decks of your private yacht rental you’ll be able to take in the scenery and get a few pictures from the unique setting of your boat rental. 

    Suggested Boats

  • Escape from boisterous crowd in Chicago, Illinois onboard Beneteau First 36.7
    $1,560 (per day)

    Escape from boisterous crowd in Chicago, Illinois onboard Beneteau First 36.7
    Chicago, IL

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  • Explore Chicago onboard 36' cruising monohull
    $452 (per ¼ day)

    Explore Chicago onboard 36' cruising monohull
    Chicago, IL

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  • Experience pure comfort and luxury onboard 38' Lagoon
    $1,200 (per ¼ day)

    Experience pure comfort and luxury onboard 38' Lagoon
    Chicago, IL

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Party Boat Rentals in Chicago

chicago-sailing-sailo-party-boat-rentals

Whatever the occasion, you’ll find a boat rental on Sailo which is perfect for your party. If you’re looking for something for the boat party, or bachelor or bachelorette parties, choose one of our smaller motor yachts. Or, if you’re looking to host the event of the year, choose one of our luxury party boat rentals. You’ll be able to accommodate anything from ten close friends, to hundreds of guests on board one of our premium boat charters. 

    Suggested Boats

  • Party hard in Chicago on a sleek motor yacht
    $31,740 (per ¼ day)

    Party hard in Chicago on a sleek motor yacht
    Chicago, IL

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  • Set sail in Chicago on luxurious & comfortable motor yacht
    $7,000 (per ¼ day)

    Set sail in Chicago on luxurious & comfortable motor yacht
    Chicago, IL

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  • Charter this stunning 105' motor yacht in Chicago
    $3,500 (per ¼ day)

    Charter this stunning 105' motor yacht in Chicago
    Chicago, IL

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A romantic sundowner

chicago-sailing-sailo-boat-rental-sunset-cruise

Is there anything more romantic than watching the sun set behind the twinkling lights of the big city? Enjoying a Chicago sailing trip at sunset is one of the best things to do if you’re looking for a special surprise for a loved one. With a Sailo boat rental you’ll be able to step on board for an unforgettable excursion. Now, if you’re thinking of popping the question then this could be the most spectacular setting! Take a look at the choice of Chicago yacht charters to find your perfect rental. 

 

    Suggested Boats

  • Explore Chicago onboard 36' cruising monohull
    $452 (per ¼ day)

    Explore Chicago onboard 36' cruising monohull
    Chicago, IL

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  • Have fun in Chicago, Illinois aboard 60' luxurious motor yacht
    $2,660 (per ¼ day)

    Have fun in Chicago, Illinois aboard 60' luxurious motor yacht
    Chicago, IL

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  • 50' Multi-level Yacht. Playpen, River cruises, City Winery.
    $2,100 (per ½ day)

    50' Multi-level Yacht. Playpen, River cruises, City Winery.
    Chicago, IL

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