Cheap flights from Massachusetts to Key West from $131

In general, September is the cheapest month to fly from Massachusetts to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $381. If you are unable to visit Key West during the month of September, then departing from Massachusetts during the month January is also very affordable. Most momondo users find prices during this month for around $389.

On average, the least expensive day to fly to Key West from Massachusetts is on a Sunday. momondo users have found tickets for Sunday departures for as low as $418. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Key West for around $604.

Fly from Boston Logan Intl to Key West for the best Massachusetts - Key West flight prices

You are more likely to see cheaper flights to Key West from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $448 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Massachusetts for as low as $421 on momondo.

There are 4 cabin classes available to choose from on Massachusetts to Key West flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Massachusetts to Key West.

Delta and United Airlines are the most popular carriers operating from Massachusetts to Key West

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Key West from Massachusetts according to our data. American Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 4 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.

As of October 2026, there are 1 flights per day flying from Massachusetts to Key West. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

The number of flights available between Massachusetts and Key West is 8 per week as of October 2026. The most frequent departure day is Mon, with 25% of weekly flights leaving on this day.