Monday Night Blues Concert Series Brings Live Music Aboard Tall Ship Windy in Chicago

CHICAGO – If you’re looking to shake off your Monday blues in the most unforgettable way, hop aboard the 148-foot Tall Ship Windy for a one-of-a-kind live blues concert on Lake Michigan. The Monday Night Concert Series is sailing strong this August, pairing the rhythm of the blues with stunning skyline views and lakefront breezes.
Live Blues Meets Lake Michigan
Each Monday evening, the Monday Night Blues series invites guests to board the historic Tall Ship Windy and immerse themselves in Chicago’s blues legacy. From newcomers discovering the genre to long-time fans chasing that authentic sound, this floating stage offers something special for everyone.
Guests enjoy stunning waterfront views, a full-service bar, and the soulful sounds of Grammy Elected and Chicago Blues Hall of Famer Michael Charles, along with a rotating lineup of performers throughout the season.
“You can’t beat watching the sunset over the skyline with a blues solo soaring above the sails,” said one recent attendee. “It’s pure Chicago.”
What to Expect on Board
- Date: Every Monday night
- Location: Aboard Tall Ship Windy, sailing from Navy Pier
- Music: Blues genre, featuring top performers like Michael Charles
- Amenities: Full bar, friendly crew, and a scenic, relaxing sail
- Atmosphere: Laid-back, soulful, and perfect for date nights or solo escapes
- Tickets: Available now via Choose Chicago
Each week’s performance showcases a unique interpretation of the blues, reminding listeners of the genre’s roots and evolution. Whether you’re swaying to harmonica solos or soaking in a guitar-heavy jam, you’re in for a night of musical storytelling and lakeside magic.
Part of Chicago’s Larger Music Revival
Chicago’s live music scene is in full swing this summer, and Monday Night Blues has carved out a niche as one of the city’s most atmospheric concert experiences. With so many land-based festivals packing crowds, this floating stage offers something refreshing — and refreshingly calm.
Have you ever experienced live music on the water? Share your best concert memories or let us know who you’d like to see aboard Tall Ship Windy this summer at ChicagoMusicGuide.com!