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Kentucky

$29+ Cheap flights from Massachusetts to Kentucky

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheap flight deals from Massachusetts to Kentucky

Keep the following information in mind while searching for Massachusetts to Kentucky flight deals. Data was last updated julio 31, 2025.

Round-trip from

$82
(Cheapflightsfares)

One-way from

$29
(Cheapflightsfares)

Popular in

May

Cheapest in

August

Average price

$403

Good round-trip deal

$289 or less

Good one-way deal

$130 or less
From Massachusetts to Kentucky
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One-way flight from Massachusetts to Kentucky
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Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Massachusetts to Kentucky.
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Price to beat on a one-way flight from Massachusetts to Kentucky.
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Find flight deals from Massachusetts to Kentucky

Cheapest flights from Massachusetts to Kentucky
Explore the most affordable flight options available from Massachusetts to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/811:00 amALB - BNA
Nonstop2h 21mAllegiant Air
lun. 9/157:00 amBNA - ALB
Nonstop2h 10mAllegiant Air
Deal found 7/30$82
This FlightHub deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/216:15 pmBDL - BNA
1 stop6h 05mSpirit Airlines
lun. 8/256:45 amBNA - BDL
Nonstop2h 20mSpirit Airlines
Deal found 7/31$87
This CheapOair deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3012:18 pmBOS - BNA
Nonstop2h 52mSpirit Airlines
lun. 11/33:15 pmBNA - BOS
Nonstop2h 43mSpirit Airlines
Deal found 7/29$95
This Gotogate deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/2311:03 amBOS - TYS
Nonstop2h 28mAllegiant Air
dom. 8/247:30 amTYS - BOS
Nonstop2h 14mAllegiant Air
Deal found 7/30$103
This Breeze Airways deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/267:15 amBDL - CVG
Nonstop2h 08mBreeze Airways
mar. 9/28:52 pmCVG - BDL
Nonstop2h 00mBreeze Airways
Deal found 7/29$128
This Flysmarter deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/218:59 pmBOS - BNA
Nonstop2h 53mJetBlue
lun. 8/257:10 amBNA - BOS
Nonstop2h 34mJetBlue
Deal found 7/30$145
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/52:35 pmALB - BNA
Nonstop2h 20mSouthwest
vie. 9/126:05 pmBNA - ALB
1 stop3h 55mSouthwest
Deal found 7/31$147
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/58:35 pmBOS - BNA
Nonstop2h 58mDelta
lun. 9/86:47 pmBNA - BOS
Nonstop2h 40mDelta
Deal found 7/31$157
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/2612:04 pmBOS - TYS
Nonstop2h 28mMultiple Airlines
mié. 8/277:15 amTYS - BOS
2 stops15h 57mMultiple Airlines
Deal found 7/31$161
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/55:00 amBOS - BNA
Nonstop2h 40mSouthwest
lun. 9/85:25 amBNA - BOS
1 stop6h 35mSouthwest
Deal found 7/31$168
This American Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/156:00 pmBOS - BNA
1 stop5h 51mAmerican Airlines
lun. 8/186:37 amBNA - BOS
1 stop4h 48mAmerican Airlines
Deal found 7/30$177
This Mytrip deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/811:00 amALB - BNA
Nonstop2h 21mMultiple Airlines
lun. 9/155:05 amBNA - ALB
2 stops11h 11mMultiple Airlines
Deal found 7/31$192

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Kentucky that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 31, 2025.
Use the filters below to find and compare flights from Massachusetts to Kentucky that are best for you.

Fly from

Massachusetts

Fly to

Kentucky

Route

Depart

Return

Price

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

lun. 9/8

11:00 am-12:21 pm

Nonstop2h 21m

Nashville Intl

lun. 9/15

7:00 am-10:10 am

Nonstop2h 10m

$82

HartfordNashville

BDL - BNA

BDLBNA

Hartford Bradley Intl

jue. 8/21

6:15 pm-11:20 pm

1 stop6h 05m

Nashville Intl

lun. 8/25

6:45 am-10:05 am

Nonstop2h 20m

$87

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

jue. 10/30

12:18 pm-2:10 pm

Nonstop2h 52m

Nashville Intl

lun. 11/3

3:15 pm-6:58 pm

Nonstop2h 43m

$95

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

sáb. 8/23

11:03 am-1:31 pm

Nonstop2h 28m

Knoxville McGhee Tyson

dom. 8/24

7:30 am-9:44 am

Nonstop2h 14m

$103

HartfordCincinnati

BDL - CVG

BDLCVG

Hartford Bradley Intl

mar. 8/26

7:15 am-9:23 am

Nonstop2h 08m

Cincinnati Cinci./N. Kentucky

mar. 9/2

8:52 pm-10:52 pm

Nonstop2h 00m

$128

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

jue. 8/21

8:59 pm-10:52 pm

Nonstop2h 53m

Nashville Intl

lun. 8/25

7:10 am-10:44 am

Nonstop2h 34m

$145

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

vie. 9/5

2:35 pm-3:55 pm

Nonstop2h 20m

Nashville Intl

vie. 9/12

6:05 pm-11:00 pm

1 stop3h 55m

$147

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

vie. 9/5

8:35 pm-10:33 pm

Nonstop2h 58m

Nashville Intl

lun. 9/8

6:47 pm-10:27 pm

Nonstop2h 40m

$157

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

vie. 10/17

9:18 am-9:12 am

1 stop24h 54m

Nashville Intl

dom. 10/19

3:15 pm-6:58 pm

Nonstop2h 43m

$160

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

mar. 8/26

12:04 pm-2:32 pm

Nonstop2h 28m

Knoxville McGhee Tyson

mié. 8/27

7:15 am-11:12 pm

2 stops15h 57m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Kentucky

What is the cheapest month to book a flight from Massachusetts to Kentucky?

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $299). Flying from Massachusetts to Kentucky in April is currently the most expensive (average of $369). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to KY?

Find hourly flight availability from Massachusetts to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 31, 2025.

When flying from Massachusetts to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Massachusetts to Kentucky

Explore weekly flight availability from Massachusetts to Kentucky. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated julio 31, 2025.

The most flights from USMA to USKY are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated julio 31, 2025.
See what other customers who have flown with Southwest, Delta, and Breeze Airways from Massachusetts to Kentucky have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Massachusetts to Kentucky one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $29. However, be on the lookout for offers from Allegiant Air and Breeze Airways, as they are both options that can get you from Massachusetts to Kentucky for a low price.

  • Can I find deals for flights from Massachusetts to Kentucky that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Kentucky.

  • Can I find deals for business class flights from Massachusetts to Kentucky?

    Yes. Cheapflights offers flight deals from Massachusetts to Kentucky by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Kentucky?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $299). Flying from Massachusetts to Kentucky in April is currently the most expensive (average of $369). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Massachusetts to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Massachusetts to Kentucky

Discover the top 5 airlines that operate flights from Massachusetts to Kentucky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$157Average$230FlexibilityNo cancel feeOn-time65%
DeltaCheapest$228Average$430FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$249Average$448FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$253Average$419FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$396FlexibilityNo cancel feeOn-time63%

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