Monday Night Concert Series Sail in Chicago 2025
Difficulty
easy
Duration
2 hours
Fitness Level
No special fitness level required; easy for most ages and abilities as the tour is seated and relaxed.
Overview
Enjoy live blues music aboard the Tall Ship Windy on a 2-hour Monday night concert sail. Discover stunning Chicago skyline views in a lively, relaxed setting.
Traditional Chicago Blues ~LIVE~ with Michael Charles!!
All ages • 2 Hours • Chase your Monday BLUES away!
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About This Adventure
Join us for a captivating 2-hour concert sail every Monday this summer aboard the Tall Ship Windy. Experience the magic of blues music while enjoying stunning views of Chicago's skyline. With talented artists and a full bar, this unique event promises to chase away your Monday blues in style.
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer.
About
We’ll help you chase your Monday BLUES away aboard the 148-foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues. Whether you're a long-time fan or a newcomer to the blues, you're sure to be transported by the talent and passion of each amazing artist. With a full bar and a friendly, knowledgeable crew, you'll be able to relax and enjoy the music in comfort and style.
Each concert will bring a unique twist to the blues genre, showcasing the diversity and versatility of this legendary music form. We’ll be joined by music’s greats, including Grammy-nominated Michael Charles and his band, and other artists throughout the season.
Tall Ship Windy’s Monday Blues is set to become the concert event of the summer! Book your tickets now and experience the magic of blues music against the backdrop of one of the world's most beautiful skylines.
Adventure Tips
Arrive Early for Best Seating
Getting to the dock at least 15 minutes before departure ensures you grab a prime spot with great views and easy access to the bar.
Dress in Layers
Even summer evenings on Lake Michigan can get cool, so bring a light jacket or sweater to stay comfortable.
Bring Cash or Card for the Bar
A full bar is available onboard with drinks and snacks; be prepared with your preferred payment method.
Check Weather Before You Go
Lake conditions impact sailings; strong winds or storms may cause cancellations, so monitor weather updates closely.
Local Insights
Wildlife
- Seagulls soaring above the lake
- Occasional sightings of river otters near the shoreline
History
Tall Ship Windy reflects Chicago’s maritime heritage, preserving traditional sailing vessels on Lake Michigan.
Conservation
The company practices eco-friendly operations to minimize fuel use and protect lake water quality.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Light Jacket or Sweater
Protects against evening chills and lake breezes.
summer specific
Comfortable Shoes
Non-slip shoes help with safe boarding and walking on deck.
Sunscreen
Useful for early evening sun exposure on the water.
spring specific
Camera or Smartphone
Capture stunning views of Chicago’s skyline at sunset.