Cheap flights from Kentucky to Massachusetts from $56

In general, September is the cheapest month to fly from Kentucky to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $331. If you aren’t able to travel to Massachusetts during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $347.

According to our data, Saturday is the cheapest day to fly to Massachusetts from Kentucky. The lowest ticket price found for a Saturday departure recently was $391. 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, Sunday is the most expensive day to depart from Kentucky because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,075.

Our data shows that the cheapest Kentucky to Massachusetts flights are usually those with departure times at noon. Our users have found flights to Massachusetts at noon for as low as $398. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $661 on average. Flights to Massachusetts from Kentucky in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Louisville Intl to Boston Logan Intl for the best Kentucky - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $370 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Kentucky for as low as $308 on momondo.

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

Allegiant Air, Frontier, and Delta are the most popular carriers operating from Kentucky to Massachusetts

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Massachusetts from Kentucky according to our data. American Airlines is the first choice among our users, with 60% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 5 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of February 2026, 33 flights take off from Kentucky and land in Massachusetts each day. The most common flight departure time for this route is 10:00AM, with 51% of daily flights taking off at noon.

As of February 2026, there are 235 flights per week flying from Kentucky to Massachusetts. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.