$52 Find Cheap Flights from Kentucky to Massachusetts

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Low seasonJanuary
Cheapest flight$52
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Knoxville to Boston

FAQs for booking flights from Kentucky to Massachusetts

  • How does KAYAK find such low prices on flights from Kentucky to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kentucky to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kentucky to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Kentucky to Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Kentucky to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Kentucky to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kentucky to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Kentucky to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Massachusetts?

    Kentucky and Massachusetts are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (8 flights per week), Air France (7 flights per week), and British Airways (7 flights per week).

  • How many airports are there in Massachusetts?

    There are 6 airports in Massachusetts. The busiest airport is Boston Logan Airport (BOS), with 96% of all flights arriving there.

  • Which is the cheapest airport to fly into in Massachusetts?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $378.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Saturday where round-trip tickets can be as cheap as $385. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $998 on average.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $397 on average. Morning departures are around 28% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $619.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Kentucky found in the last 72 hours was to Boston, at $295 round-trip. The most popular route is Louisville (SDF) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $295.

  • What is the cheapest month to fly from Kentucky to Massachusetts?

    The cheapest month for flights from Kentucky to Massachusetts is August, when tickets cost $303 (return) on average. On the other hand, the most expensive months are April and June, when the average cost of round-trip tickets is $489 and $471 respectively.

  • How far in advance should I book a flight from Kentucky to Massachusetts?

    To get a below average price on the flight from Kentucky to Massachusetts, you should book around 5 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

  • How many cities have direct flights to Massachusetts?

    From Kentucky, there are direct flights to Massachusetts from 1 city. This city is Louisville and there are 42 direct flights each week.

  • How many direct flights to Massachusetts are there each day?

    There are around 6 direct flights from within Kentucky to Massachusetts every day. Most flights (50%) depart in the afternoon.

  • How many direct flights to Massachusetts are there each week?

    Each week there are around 42 direct flights from within Kentucky to Massachusetts. The most common day for departures is Sunday, with 29% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Kentucky to Massachusetts takes 6h 16m, covering a distance of 783 miles. The shortest route is Cincinnati (CVG) to Hartford (BDL) with an average flight time of 2h 02m.

  • How many long-haul flights are there to Massachusetts each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Massachusetts. Instead, there are 42 short-haul flights (up to 3 hour flight duration), with the most arriving from Louisville.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (80% of total searches to Massachusetts). The next most popular destinations are Hartford (13%) and Albany (6%). Searches for flights to Provincetown (0%) are also popular.

Reviews of the top 5 airlines serving from Kentucky to Massachusetts

 
Need help choosing which airline to fly with from Kentucky to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4309 reviews
7.0Food
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

4.0 OkayEmma, Mar 2026
LAX - PHX
Read more Southwest reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

They changed our boarding gates at the last minute! No one at gate told us! It was finally announced over loud speaker but the person spoke very broken English and couldn’t understand!! Just went to information board to confirm. Had a “ medical emergency “ they called it and we couldn’t use bathrooms ( I understand) The flight attendant allowed the teenager sitting in my row to move to be with friend? Would have loved the same from my husband at back of plane! Why did attendant ask me twice to push my bag under the seat and NEVER once said anything to man in aisle across from me?? His was laying in floor!! Rate food? What food? Just drinks were offered for a price. Should be against the law to charge $5 for water. No… not the best flight.

The bag situation was confusing. I didn’t know I had to pay for Carry ons. The seats were uncomfortable and there was no entertainment

Spirit Airlines at Laguardia is a small terminal so it is quick to get to your gate and to get your luggage. The flight is short enough to orlando and the price was very inexpensive. The seats do not move so you can't recline. Drinks and snakcks should be complimentary.

Bad. I know TSA is a mess right now but they “overbooked” the flight and almost didn’t let 10 of us on. Can’t put even a normal backpack under the seat, tray table is barely a foot wide, have to pay for literally everything. Apparently you can bid on your seats, too, so really the baseline ticket only covers the possibility of maybe getting on the plane. The staff were nice though, can only imagine the stress they are under.

I was double booked for my ticket- they have record of it and admitted to their error but wouldn’t let me board until I paid once again for the fare- have documentation of their mistake -

The flight time did not match my original email on time of flight. Missed the first flight. The representative I got on the phone was so incompetent it was unbelievable. My guess is it was AI but it told me it was not AI. They did get me rebooked which I was very thankful of. The return flight was delayed because of staffing issues for the plane and when we reached our destination the jet bridge would not work so we sat on the plane another 40 minutes. I did get to my destination and I did get home but not a good experience.

My flight was cancelled I missed time at work and got a parking ticket

It was terrible. I had to pay again once I got to the airport because they said they never received the payment.

Customer service online / on the phone are horrible. Flight crew is great but gate agents and customer service are terrible

bought basic spirit fares, add checked bags - like the up front info on website about this. bring your own snacks, buy a soda after TSA security to bring with you, or buy on the plane (limited selection) all in all, a good experience

Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Kentucky

Cabin classes available on flights to Kentucky. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.