Cheap flights from Kentucky to Boston from $55

In general, October is the cheapest month to fly from Kentucky to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $125. If you aren’t able to travel during the month of October, then book flights to Boston from Kentucky during May instead. Flights to Boston in May, while not as cheap as those in October, still average around $135.

The cheapest day to depart from Kentucky to Boston is on a Saturday when prices can be found for as low as $435. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $1,205.

According to our data, the cheapest time of day to fly to Boston is at noon. momondo users have found flights departing from Kentucky to Boston at noon for as low as $508. 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 $682 per ticket.

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

You are more likely to see cheaper flights to Boston from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $399 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Kentucky for as low as $314 on momondo.

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

United Airlines, Delta, and Southwest are the most popular carriers operating from Kentucky to Boston Logan Intl

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Boston from Kentucky 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 Boston. Keep in mind that there are 4 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

As of July 2026, there are 34 flights per day flying from Kentucky to Boston. The most common time of day flights depart is 12:00PM, with 100% of flights taking off in the afternoon.

As of July 2026, there are 241 flights per week flying from Kentucky to Boston. The most common day of the week flights depart is Wed, with 22% of flights taking off on this day.