Cheap flights from Boston to Key West from $131

In general, September is the cheapest month to fly from Boston 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 Boston 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 Boston 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 Boston to Key West for around $604.

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

You are more likely to see cheaper flights to Key West from Boston 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 Boston for as low as $421 on momondo.

There are 4 cabin classes available to choose from on Boston 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 Boston to Key West.

Delta and United Airlines are the most popular carriers operating from Boston Logan Intl to Key West

American Airlines, JetBlue and Delta are the top three most popular airlines that fly to Key West from Boston according to our data. American Airlines is the first choice among our users, with 59% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 5 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.

Miami (MIA) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $321.

Flights connecting via Miami (MIA) have the shortest average one-way travel time: 5h 35m.

Miami (MIA) has the shortest average layover time for this route: 0h 51m.

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

As of October 2026, there are 10 flights per week flying from Boston to Key West. The most common day of the week flights depart is Mon, with 20% of flights taking off on this day.