Cheap flights from Fort Myers to Massachusetts from $165

In general, January is the cheapest month to fly from Fort Myers to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $209. If you aren’t able to travel to Massachusetts during the month of January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $248.

According to our data, Friday is the cheapest day to fly to Massachusetts from Fort Myers. The lowest ticket price found for a Friday departure recently was $309. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Wednesday is the most expensive day to depart from Fort Myers because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $377.

Our data shows that the cheapest Fort Myers to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $289. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $406 on average. Flights to Massachusetts from Fort Myers in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Fort Myers SW Florida Intl to Boston Logan Intl for the best Fort Myers SW Florida Intl - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Fort Myers when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $311 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Fort Myers for as low as $261 on momondo.

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

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Fort Myers SW Florida Intl to Massachusetts

JetBlue, Delta and Allegiant Air are the top three most popular airlines that fly to Massachusetts from Fort Myers according to our data. JetBlue is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 6 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of October 2026, there are 13 flights per day flying from Fort Myers to Massachusetts. The most common time of day flights depart is 3:00PM, with 61% of flights taking off at noon.

The number of flights available between Fort Myers and Massachusetts is 91 per week as of October 2026. The most frequent departure day is Sun, with 24% of weekly flights leaving on this day.