Experience the Monday Night Blues Summer Concert Series in Chicago’s Vibrant Waterfront Scene
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels as the event involves mostly standing or sitting on deck with minimal physical exertion.
Overview
Set sail on a historic tall ship while enjoying live blues music against Chicago’s stunning skyline. Discover why the Monday Night Blues Summer Concert Series offers a unique blend of culture and adventure on Lake Michigan.
Monday Night Blues Summer Concert Series
Chase your Monday BLUES away aboard Tall Ship Windy
Select participants and date
Adventure Photos
About This Adventure
Experience the magic of summer with a 2-hour concert sail aboard the Tall Ship Windy every Monday evening. Enjoy breathtaking views of Chicago while talented blues artists, including Grammy-nominated Michael Charles, serenade you. With a full bar and a welcoming crew, this unique event promises unforgettable music and stunning scenery.
Kick-off your week and join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer.##
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
Boarding begins 30 minutes before departure; arriving early helps secure prime spots on the deck for optimal views.
Dress in Layers
Lake Michigan evenings can be cool even in summer—bring a light jacket to stay comfortable during the concert.
Check Weather Before You Go
Wind and rain can affect sailing conditions; verify the forecast and event status prior to arrival.
Use Public Transit or Ride Share
Navy Pier parking can fill up quickly; public transit or ridesharing are recommended for easy access and less hassle.
Local Insights
Wildlife
- Common sighting of gulls soaring over Lake Michigan.
- Occasional glimpses of river otters near the marina areas.
History
Chicago’s blues scene blossomed in the early 20th century, fueled by Great Migration artists who shaped the city’s musical identity.
Conservation
The concert series promotes sustainability by encouraging public transit and minimizing single-use plastics on board.
Select participants and date
Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Light Jacket
Protects against cooling lake breezes during evening concerts.
summer specific
Comfortable Footwear
Non-slip shoes help navigate the ship’s deck safely.
Sunscreen
Use if attending early evening to protect from sun exposure near the water.
summer specific
Camera or Smartphone
Capture stunning skyline views and live music moments from the deck.