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Sailing the Windy City: Experience Chicago from the Tall Ship Windy

Explore Chicago's skyline and waterfront on a historic tall ship with Tall Ship Windy, offering unique sailing experiences and breathtaking views.

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Set sail on an unforgettable adventure with Tall Ship Windy in Chicago, where you can explore the city's stunning skyline and vibrant waterfront aboard a majestic tall ship. Perfect for tourists of all ages, this sailing experience offers breathtaking views, educational tours, and the chance to learn about sailing techniques.

A brief summary to Tall Ship Windy

  • Monday 10 am-7 pm
  • Tuesday 10 am-7 pm
  • Wednesday 10 am-7 pm
  • Thursday 10 am-7 pm
  • Friday 10 am-7 pm
  • Saturday 10 am-7 pm
  • Sunday 10 am-7 pm

Local tips

  • Book your tickets online in advance to secure your preferred sailing time and avoid long lines.
  • Dress in layers, as it can be windy and cooler on the water, even during warmer months.
  • Arrive early to enjoy the sights at the dock and take advantage of photo opportunities with the ship.
  • Check the calendar for special themed sails, such as sunset cruises or live music events, for a unique experience.
  • Bring a camera to capture the stunning views of Chicago's skyline from the water.
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Getting There

  • Public Bus

    From Oak Lawn, walk to the nearest bus stop for the Pace Bus 382 route towards Chicago. Board the bus and remain on it until you reach the 'Harvey Transportation Center' stop. Here, transfer to the Metra Electric Line at the Harvey station. Take the train towards Millennium Station in Chicago. Once you arrive at Millennium Station, exit the train and walk towards the exit that leads to Michigan Avenue. From there, head east on East Randolph Street until you reach the lakefront. Turn right onto East Grand Avenue and walk straight for about 15 minutes until you reach 600 E Grand Ave, where Tall Ship Windy is located.

  • Train and Walk

    Make your way to the Oak Lawn Metra Station, located at 9500 Southwest Hwy. Take the Metra’s SouthWest Service train toward Chicago Union Station. Get off at the Union Station stop. Once you exit the station, walk towards the south and head towards the Ogilvie Transportation Center. From Ogilvie, follow signs to the 'Lyric Opera' and take the stairs down to the street level. Continue walking east on West Randolph Street until you reach North Michigan Avenue. Turn left and head north until you reach East Grand Avenue. Turn right on East Grand Avenue and continue walking until you reach 600 E Grand Ave, the location of Tall Ship Windy.

  • Taxi or Rideshare

    If you prefer a more direct route, you can use a taxi or rideshare service like Uber or Lyft. Simply request a ride to '600 E Grand Ave, Chicago, IL 60611'. The driver will take you directly to your destination. Ensure to confirm your pickup location in Oak Lawn for the smoothest experience.

Unlock the Best of Tall Ship Windy

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Discover more about Tall Ship Windy

Nestled along the scenic shores of Lake Michigan, Tall Ship Windy offers tourists a unique opportunity to experience Chicago's stunning skyline from the water. This beautiful, historically-inspired tall ship provides daily sailing excursions that allow guests to soak in breathtaking views of iconic landmarks such as Navy Pier, the John Hancock Center, and the Willis Tower. Whether you’re a seasoned sailor or a newcomer to the seas, the friendly and knowledgeable crew is dedicated to making your journey both enjoyable and enlightening. During the sail, passengers can not only relax and take in the views but also participate in the sailing process, learning the ropes and even hoisting the sails, making it an interactive experience for all aboard. The ship itself is a replica of an 1816-era tall ship, adding to its charm and allure. In addition to regular sailing tours, Tall Ship Windy offers themed sails, including sunset cruises and special events that can elevate your experience to something truly memorable. Families, couples, and solo travelers alike will find something to cherish during their time on the water. The ambiance on board is both cheerful and relaxing, ensuring that visitors can unwind while surrounded by the beauty of Chicago's waterfront. With a commitment to safety and environmental stewardship, Tall Ship Windy is not just a boat tour; it’s a celebration of the city’s maritime heritage and natural beauty. Plan your visit to embark on an unforgettable sailing adventure that highlights the best of the Windy City’s stunning surroundings.

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