Skip to primary navigation Skip to content Skip to footer
  • Every night at 5pm!

Happy Arr-our Chicago Architecture and Skyline Sail

All ages welcome. Happy hour specials for guests 21+, with valid ID.

Quick Details

General Admission Boarding
Adult Ages 13+
Child Ages 0-12
VIP Captains Boarding
Adult Ages 13+
Child Ages 0-12

Enjoy onboard happy hour drink specials every night at 5pm

It’s the perfect way to end your workday or kick off your weekend plans. Set against the stunning backdrop of the Chicago skyline, Tall Ship Windy becomes the ultimate venue to unwind and soak in breathtaking views from the water. It’s not just a happy hour; it’s an experience that elevates your evenings and sets the tone for a fantastic night ahead.

Experience breathtaking views of the Chicago skyline from the water!

Leave the hustle and bustle behind and explore Chicago’s gorgeous shores with a leisurely trip on Lake Michigan. Sail on Tall Ship Windy and immerse yourself in the world-famous skyline of Chicago, revel in spectacular views and uncover the secrets of the Windy City from the unique vantage point of the water.

Join us on the main deck, where lively and educational narrations bring to life the people, plans and persistence that shaped Chicago’s most iconic landmarks. It’s not just a tour; it’s a voyage through time and architecture, where each moment on board becomes a chapter in the story of Chicago’s rich tapestry. Let the city’s history unfold before your eyes as you sip on daily happy hour specials. Cheers to unforgettable moments on the water!