Sailing in West Loop


Select Local Merchants

  • Offshore Adventures Chicago
    The 35-foot Alpha Puppy and the 30-foot Sundog could be the names of two extremely long dachshunds, but they're actually the two boats comprising Offshore Adventures Chicago's fleet. Captain Rick, a USCG Master Captain, helms the boats on the company's Lake Michigan cruises, with routes that highlight views of the city's skyline. As he steers, passengers enjoy beverages they brought along and listen to their personal playlists rather than the music of a nearby seagull pecking its xylophone. During the summer, twice-weekly night cruises augment the typical cruise selections and offer spectacular views of the city's fireworks displays.
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    321 S. Sangamon #810
    Chicago, IL US
  • Corporate Tailgate and Boat Rentals
    During summer months, the night sky above Lake Michigan bursts to life with booming colors. Fireworks displays launch from Navy Pier every Wednesday and Saturday, and crowds gather to marvel at the spectacle. However, the best views are arguably on the water, where boats float beneath the glow of explosions. Not all of these spectators own their own boats. Some sit aboard vessels from Corporate Tailgate and Boat Rentals. The company transforms its customers into temporary captains of yachts and electric boats, which groups can use to tour Chicago's waters. They might have lunch out on Lake Michigan or travel the Chicago River, passing by the city's renowned waterfront architecture and that one building everyone pretends to like.
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    800 South Wells Street
    Chicago, IL US
  • SideTour - Leisure
    Sound Excursions describes their carefully curated group experiences as "field trips for adults." It's easy to see why: every outing takes groups to a new realm of Washington, whether it's the frothy shores of Puget Sound, inland forests and mountains, or tables at Seattle's thriving restaurants. The events held at these diverse locations range from culinary workshops on topics such as sushi-making and moonshine-tasting, to adventurous excursions with whitewater rafting or kayaking, to laid-back themed party cruises. For many outings, luxury transportation is provided.
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    116 Hubbard St.
    Chicago, IL US
  • Chicago First Lady
    The history buffs of Chicago's Finest Tours lead engaging and dynamic tours of two very different parts of the city. During the summer, intimate groups of up to 20 traverse the various walkways of the bustling yet majestic riverfront or climb aboard a boat for a sunny river voyage, soaking in vistas of Chicago's many architectural wonders. In the winter, tourgoers head below the sidewalks with torch in hand to explore the troll-populated tunnels of the Pedway, Chicago's underground network of shops, hotels, train stations, and eateries. Regardless of the tour, the knowledgeable guides engage strollers in a two-way conversation about the Windy City, enlightening audiences with historical yarns and humorous anecdotes.
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    112 East Wacker Drive
    Chicago, IL US
  • Wendella Sightseeing Boats
    Wendella’s boats have sailed Chicago’s waters since 1935, when founder Albert Borgström built the company’s first ship by hand. Still run by Albert’s great grandson, Michael, the company complements its time-tested architecture and history tours with specialty tours that feature beer and barbecue, wine and cheese, or fireworks. Wendella also operates Chicago’s distinctive yellow-and-black water taxis.
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    400 N Michigan Ave
    Chicago, IL US
  • Wateriders Kayak Tours
    Situated on the Riverwalk of the popular 600 West Chicago Ave building, Wateriders Kayak Tours and Rentals' experienced and knowledgeable guides have been leading relaxed kayak tours down Chicago’s picturesque waterways since 1997. Day and night tours explore the city's most exciting attributes, focusing on history, architecture, and eerie mob chronicles as guides provide paddling instruction and share true tales of Al Capone's mythical collection of tracksuits. Wateriders also rents its kayaks to independent paddlers who prefer to discover Chicago's sights on their own.
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    950 N Kingsbury St.
    Chicago, IL US

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