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The Iconic Chicago Skyline: A Symphony of Architecture


When you think of iconic city skylines, few can rival the breathtaking panorama of the Chicago skyline. Nestled along the southwestern shores of Lake Michigan, this architectural marvel is a testament to human ingenuity, ambition, and the relentless pursuit of the sky. In this blog, we will explore what makes the Chicago skyline an unparalleled work of art.

Chicago Skyline Sail Aboard 148' Tall Ship Windy
  • Most Popular!
From $39 per Person

Explore Chicago’s scenic shores and enjoy this Windy City boat tour with a relaxing sail around Lake Michigan. Take in the world-famous Chicago skyline, enjoy spectacular city views and discover the Windy City from the water. Select from Pirates and Maritime stories at 1pm, Architectural Tour and Skyline at 3pm and 5pm or a Chicago Sunset Cruise at 7pm.

Chicago Skyline Sunset Sail
  • Frequently Sells Out
From $49 per Person

For the best Chicago sunset, visitors and residents alike, join us aboard the 148′ Tall Ship Windy – the official ambassador for the City of Chicago. Departing from Navy Pier daily, you will enjoy a spectacular sailing cruise and enjoy the breathtaking moments as the sun sets gently behind the Chicago Skyline. There is nothing like Chicago at sunset.

Fireworks Cruise From Navy Pier Aboard Tall Ship Windy! From $50 per Person

Watching fireworks from Navy Pier has become a Chicago tradition and there is no better seat in the house to watch the show than sailing aboard 148′ Tall Ship Windy – the Official Flagship of the City of Chicago! Order a cold drink from our bar and enjoy a thrilling fireworks performance as you sail along the stunning and iconic Chicago skyline during this special event sail.