Chapter 11 Reorganization Filing – Seeking Investors To Revive Seaplane Routes Tailwind Air, based out of Westchester County Airport in New York and Sikorsky Memorial Airport in Connecticut, filed for Chapter 11 protection in the Eastern District of Virginia bankruptcy court on Jan. 15, 2026. Tailwind launched in 2014 and began flying commercially in 2019 after securing its licenses. The airline struggled to turn a profit and ultimately canceled all commercial flights, transitioning to a charter-only operation in 2024 after citing weak demand and mounting losses. Plans to operate charter flights also failed, and the airline lost its air operator certificate in January 2025, effectively grounding its fleet.
