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Kentucky

$63+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Jan 19 — Jan 261
Mon 1/19
Mon 1/26
1 adult, Economy
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Cheap 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 December 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:20 pmALB - BNA
Nonstop2h 25mAllegiant Air
Wed 12/3110:58 amBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/19$135
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:22 pmALB - BNA
Nonstop2h 25mAllegiant Air
Wed 12/3110:58 amBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/19$177
This Kiwi.com deal was found by Cheapflights users on 12/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:20 pmALB - BNA
Nonstop2h 25mAllegiant Air
Sat 1/312:24 pmBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/18$182
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Tue 12/309:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Sat 1/36:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
Deal found 12/19$186
This Cheapflightsfares deal was found by Cheapflights users on 12/19. 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.
Wed 12/318:20 pmALB - BNA
Nonstop2h 25mAllegiant Air
Sat 1/312:24 pmBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/19$187
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:22 pmALB - BNA
Nonstop2h 25mAllegiant Air
Wed 12/3110:58 amBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/19$188
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Sat 12/2010:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Thu 12/259:45 amTYS - BOS
Nonstop2h 10mAllegiant Air
Deal found 12/19$218
This Priceline deal was found by Cheapflights users on 12/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:13 amBOS - BNA
Nonstop3h 03mJetBlue
Fri 12/2612:01 pmBNA - BOS
Nonstop2h 32mJetBlue
Deal found 12/18$227
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:20 pmALB - BNA
Nonstop2h 25mAllegiant Air
Sat 12/2712:24 pmBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/19$234
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:20 pmALB - BNA
Nonstop2h 25mAllegiant Air
Mon 12/2912:19 pmBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 12/19$235
This JetBlue deal was found by Cheapflights users on 12/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:13 amBOS - BNA
Nonstop3h 03mJetBlue
Thu 1/112:01 pmBNA - BOS
Nonstop2h 32mJetBlue
Deal found 12/18$242
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Mon 12/298:08 amBOS - BNA
1 stop23h 34mFrontier
Sun 1/47:48 amBNA - BOS
1 stop22h 35mFrontier
Deal found 12/19$246

Find flight deals from Massachusetts to Kentucky

Keep the following information in mind while searching for Massachusetts to Kentucky flight deals. Data was last updated December 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$80
(Booking.com)

One-way from

$63
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$453

Good round-trip deal

$377 or less

Good one-way deal

$338 or less
Provider with most accurate pricing for Boston Logan Intl-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Louisville Intl flights.
Search Deals
From Massachusetts to Kentucky
Search Deals
One-way flight from Massachusetts to Kentucky
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Kentucky.
Search Deals
Price to beat on a one-way flight from Massachusetts to Kentucky.
Search Deals

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 December 20, 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

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

Thu 2/12

9:29 am-12:12 pm

Nonstop2h 43m

Knoxville McGhee Tyson

Sun 2/15

6:30 am-8:39 am

Nonstop2h 09m

$85

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

Thu 2/19

9:29 am-12:12 pm

Nonstop2h 43m

Knoxville McGhee Tyson

Thu 2/26

6:30 am-8:38 am

Nonstop2h 08m

$108

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Wed 1/14

2:45 pm-4:52 pm

Nonstop3h 07m

Nashville Intl

Sat 1/17

7:20 am-11:11 am

Nonstop2h 51m

$127

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Tue 1/13

7:05 am-9:05 am

Nonstop3h 00m

Nashville Intl

Wed 1/14

9:50 am-1:21 pm

Nonstop2h 31m

$127

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Wed 1/14

2:45 pm-4:52 pm

Nonstop3h 07m

Nashville Intl

Tue 1/20

7:20 am-11:10 am

Nonstop2h 50m

$127

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 1/10

5:10 am-7:10 am

Nonstop3h 00m

Nashville Intl

Sun 1/11

7:15 am-12:55 pm

1 stop4h 40m

$147

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sun 1/18

7:05 am-9:05 am

Nonstop3h 00m

Nashville Intl

Fri 1/23

9:50 am-1:21 pm

Nonstop2h 31m

$147

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 1/31

8:00 am-10:16 am

Nonstop3h 16m

Nashville Intl

Wed 2/4

6:00 am-2:17 pm

1 stop7h 17m

$147

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 1/24

12:55 pm-6:05 pm

2 stops6h 10m

Nashville Intl

Wed 1/28

7:35 am-2:20 pm

1 stop5h 45m

$152

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Fri 2/20

10:05 am-7:25 pm

1 stop10h 20m

Nashville Intl

Mon 2/23

7:25 pm-10:55 pm

Nonstop2h 30m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

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, September is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $187). Flying from Massachusetts to Kentucky in June is currently the most expensive (average of $299). 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 December 20, 2025.

It’s typically best to fly out from Massachusetts to Kentucky in the morning. Doing so could potentially save you 15% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 December 20, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines 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
4,258 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,021 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,100 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,194 reviews
Southwest
8.0
Very good
4,258 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Massachusetts to Kentucky?

    Airlines like Allegiant Air, Delta, and JetBlue fly from Massachusetts to Kentucky in about 2h 43m. The time it takes to get you to your destination is usually consistent. Massachusetts and Kentucky are separated by a distance of 829 mi. Most flights are nonstop.

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

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $124. However, be on the lookout for offers from Delta and United Airlines, 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, September is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $187). Flying from Massachusetts to Kentucky in June is currently the most expensive (average of $299). 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

Browse thousands of different options on Cheapflights for your next trip

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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 December 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$119Average$241FlexibilityNo cancel feeOn-time65%
DeltaCheapest$240Average$419FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$397FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$248Average$412FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$286Average$401FlexibilityNo cancel feeOn-time63%

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