$54 Find Cheap Flights from Kentucky to Massachusetts

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Low seasonJanuary
Cheapest flight$54
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 12% 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?

    American Airlines connects Kentucky to Massachusetts with 7 flights per week. British Airways also offers 7 flights per week, while Delta follows with 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 95% 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 $577.

  • 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 $390. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $1,081 on average.

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

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $298 on average. Morning departures are around 35% 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 $749.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Kentucky found in the last 72 hours was to Boston, at $285 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 $285.

  • 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 February and April, when the average cost of round-trip tickets is $518 and $489 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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 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 34 direct flights each week.

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

    There are around 5 direct flights from within Kentucky to Massachusetts every day. Most flights (71%) depart in the morning.

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

    Each week there are around 34 direct flights from within Kentucky to Massachusetts. The most common day for departures is Saturday, with 18% of flights taking off on this day.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Kentucky to Massachusetts takes 7h 12m, 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 34 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 (75% of total searches to Massachusetts). The next most popular destinations are Hartford (14%) and Albany (11%). 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.
7.9
SouthwestOverall score based on 4252 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

United have really come back. Airport and boarding process is clear and good, app and information also very good

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

Customer feedback I sent to Spirited today: “I will never fly Spirit Airlines again and will work hard to convince my friends and family to boycott/avoid Spirit Airlines at all costs. I booked three seats for me and my 8 and 10 year old children on NK 1222 from Orlando to Kansas City for 12/7/25 leaving Orlando at 10:37AM. This itinerary was abandoned by Spirit and we were rebooked onto Spirit flight NK 213 leaving at 9:06PM without any notice. Then the nightmare really began. Flight 213 was delayed a total of 12 times, finally leaving at 6:35AM the following day. The gate was changed 5 times and our electronic boarding passes were invalidated at midnight. The worst part was that the 12 separate delays were incremental making it impossible to plan for accommodations for my family. My kids missed a day of school and barely slept under the harsh lights with lots of noise on the filthy airport floor. The customer service agent at Spirit Airlines told us we would be emailed a voucher for a hotel which never happened. I asked about it multiple times and it never arrived in my email inbox. This whole unfortunate situation could’ve been avoided if spirit had taken a realistic approach and delayed the flight from 9 PM until 6 AM from the beginning. My son gleefully deleted the Spirit app from my phone once we landed and we will never fly with Spirit again.”

Honestly horrible. The plane on the way back was delayed 6 times with no explanation on why. When I asked for a refund or some money back because I had to miss a day of work because of the desk, they told me no. Because of how poorly it was handled I will most likely never take spirit again

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

This was my first time on a budget airline and I couldn't even sit down all the way because my knees would embed in the seat in front of me. I'm only 6' tall with a 32" inseam. There's no upside other than y'all are cheap. I'm glad it was only a 2 hour flight. Lesson learned! I get why everybody talks down on budget airlines. The staff was outstanding, the flight went as well as possible, great pilot, great boarding, smooth sailing. Zero chance I'll be back though.

Everything was smoothly and convenient! Just stay in this way!

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Terrible Airline I will never fly that airline again. Shame on you for recommending them.

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

I didn't eat, so I can't rate the food. Delayed set off was beyond

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

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.