$51 Find Cheap Flights from Massachusetts to Kentucky

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Low seasonJanuary
Cheapest flight$51
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Boston to Knoxville

FAQs for booking flights from Massachusetts to Kentucky

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

    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 Massachusetts to Kentucky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Massachusetts to Kentucky 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 Massachusetts to Kentucky?

    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 Massachusetts to Kentucky 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 Massachusetts to Kentucky?

    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 Massachusetts to Kentucky 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 Kentucky?

    Massachusetts and Kentucky are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (9 flights per week), Delta (7 flights per week), and Air France (one flight per week).

  • How many airports are there in Kentucky?

    There are 4 airports in Kentucky. The busiest airport is Louisville Airport (SDF), with 67% of all flights arriving there.

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Kentucky is Louisville Intl Airport (SDF), with an average flight price of $343.

  • What is the cheapest day to fly to Kentucky?

    Based on KAYAK data, the cheapest day to fly to Kentucky is Saturday where round-trip tickets can be as cheap as $342. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $430 on average.

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

    The cheapest time of day to fly to Kentucky is generally in the evening, when round-trip flights cost $317 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $385.

  • What is the cheapest flight to Kentucky?

    The cheapest ticket to Kentucky from Massachusetts found in the last 72 hours was to Louisville, at $268 round-trip. The most popular route is Boston (BOS) to Louisville (SDF) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $268.

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

    The cheapest month for flights from Massachusetts to Kentucky is August, when tickets cost $333 (return) on average. On the other hand, the most expensive months are November and May, when the average cost of round-trip tickets is $445 and $412 respectively.

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

    To get a below average price on the flight from Massachusetts to Kentucky, 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 5 weeks before departure.

  • How many cities have direct flights to Kentucky?

    From Massachusetts, there are direct flights to Kentucky from 1 city. This city is Boston and there are 17 direct flights each week.

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

    There are around 3 direct flights from within Massachusetts to Kentucky every day. Most flights (88%) depart in the morning.

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

    Each week there are around 17 direct flights from within Massachusetts to Kentucky. The most common day for departures is Sunday, with 29% of flights taking off on this day.

  • How long is the flight to Kentucky?

    An average nonstop flight from Massachusetts to Kentucky takes 6h 37m, covering a distance of 795 miles. The shortest route is Hartford (BDL) to Cincinnati (CVG) with an average flight time of 2h 07m.

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

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Kentucky. Instead, there are 17 short-haul flights (up to 3 hour flight duration), with the most arriving from Boston.

  • What are the most popular destinations in Kentucky?

    Based on KAYAK flight searches, the most popular destination is Nashville (60% of total searches to Kentucky). The next most popular destinations are Cincinnati (20%) and Louisville (10%). Searches for flights to Knoxville (6%), to Lexington (3%) and to Blountville (1%) are also popular.

Reviews of the top 5 airlines serving from Massachusetts to Kentucky

 
Need help choosing which airline to fly with from Massachusetts to Kentucky? 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 4248 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

2.0 MediocreMatthew, Jan 2026
DAL - SAN
Read more Southwest reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

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.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Sitting on the runway after we land for almost two hours! Not sure if we should blame United or Just Dumpy Vance.

Hotter than Hades in August. Why, why do crews think that in the winter when we are already dressed for cold weather we need a cabin that is 82 degrees. Even the vents were blowing hot air.

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

The flight was on time and arrived early. The crew were friendly and helpful.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Experience was good. We were delayed in leaving by 15 mins because the flight was waiting on a family that was late in getting to the gate. Food and drink options were as expected. I highly recommend checking in ahead of time using the airline’s app so that it’s quicker to get your luggage tags as soon as you arrive at the terminal. No more waiting in long lines!

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

We never made it due to delays on both ends. Gate attendant said it was mechanical but the system said otherwise, so no compensation. That’s not right.

Horrible experience. First and last time using this airline. Made an announcement that boarding will start in 15 minutes, canceled the flight 5 minutes later due to no airline staff. Had to book another flight on Delta since Spirit had no other flights arriving to my original destination the same day. I wouldn't recommend anyone to fly with Spirit. No wonder why it consistently ranks high among worst airlines.

Once again, the staff seem to think they are above the customers and treat everyone with disdain, belittling people.

COMMUNICATION!!!! The issue was a crew shortage, which means you knew in advance the issue. Instead of notifying people in advance, we're finding out an hour before the flight it's canceled. You rebooked people to more flights you knew wouldn't get out. You ended by taking part of my party to a completely different state and leaving them there. The next morning, you still have no way to get them to the original destination and they ended up missing an important event. We came out of so much money to check bags multiple times. And on top of all that, the staff in the building seemed to not care and were fairly rude. Overall, just go on and fold and quit making promises to people to get them places when you know you can't. Shoutout to Delta for doing a great job at making it less painful (for those of us who made it).

Flight was canceled 8 hours before departure for lack of operational control and prepositioning of a plane. Then had the audacity to say it was because of weather, however there was no weather here in California or New Orleans or in between. It was the weather in Florida, Florida it had nothing to do with our flight path just the plane was supposed to fly us. 8 hours is more than enough time to move a plane anywhere in the US. That left me with a bill of 1200 dollars to re book a flight oh and kayaks insurance what a joke. Probably will never use kayak or spirit ever again terrible companies terrible customer service. I’ll also let everyone and anyone know this was an abomination and only for the customer. Also will be making a report to the DOT on bad business practices on behalf of kayak and spirit as well as the BBB. Do better, take care of your customers and don’t suck

The flight was cancelled without prior notice. I was inform as I was checking in. No hotel accommodation nor any simple explanation as why it was cancelled.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Flight cancelled and no alternative offered for over a week. Ruined our Christmas vacation plans

Flight was delayed from 10:09pm back to 12:41am and actually took off closer to 1am as they were waiting for an additional flight attendant. Plane was new and crew was fine once we got moving but the delay was rough. Also Spirit (have flown this twice) lands at the satellite gates at BNA and there is a ground shuttle to get you back to the main terminal that adds outdoor elements, extra walking and about 20 min total to the arrival timing. BNA may eventually connect this concourse in a better way as they grow but it’s notable.

The flight was on time, the crew is friendly, and the seat was nice and wide compared to some other airlines. (the KAYAK survey should allow for the response, not applicable, because I did not have any food or take advantage of the entertainment)

Cancel the ticket on my day that I’m travelling that it was

Everything you need to know for your flight to Kentucky

Cabin class types available on flights to Massachusetts

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