Cheap flights from Florida Keys to Boston from $91

In general, January is the cheapest month to fly from Florida Keys to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $167. If you aren’t able to travel during the month of January, then book flights to Boston from Florida Keys during February instead. Flights to Boston in February, while not as cheap as those in January, still average around $193.

The cheapest day to depart from Florida Keys to Boston is on a Thursday when prices can be found for as low as $228. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $393.

According to our data, the cheapest time of day to fly to Boston is at noon. momondo users have found flights departing from Florida Keys to Boston at noon for as low as $160. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $363 per ticket.

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

You are more likely to see cheaper flights to Boston from Florida Keys when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $223 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Florida Keys for as low as $165 on momondo.

There are 2 cabin classes available to choose from on Florida Keys to Boston Logan Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

As of April 2026, there are 24 flights per day flying from Florida Keys to Boston. The most common time of day flights depart is 12:00PM, with 100% of flights taking off in the afternoon.

As of April 2026, there are 174 flights per week flying from Florida Keys to Boston. The most common day of the week flights depart is Fri, with 19% of flights taking off on this day.