Cheap Southwest Airlines flights New York (JFK) to Key West (EYW)

Scoring cheap one-way Southwest Airlines flights from JFK to EYW on Expedia is a breeze — just filter by "Price (lowest to highest)." Or check out our affordable round-trip fares for your next exciting getaway.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Search for cheap Southwest Airlines flights from John F. Kennedy Intl. Airport (JFK) to Key West Intl. Airport (EYW) one to three months prior to your day of departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and itinerary, the best day of the week to book a domestic flight is usually Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

Filter your results by "Morning" and "Early Morning" to browse the earliest flights from JFK to EYW. Heading off early means flight cancellations are less likely.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.