Kentucky

$75+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Mar 13 — Mar 201
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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 February 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 6/197:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Fri 6/2610:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Deal found 2/10$122
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Fri 6/57:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Mon 6/810:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Deal found 2/7$123
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Fri 6/197:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Mon 6/2910:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Deal found 2/10$128
This Booking.com deal was found by Cheapflights users on 2/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:30 am
BOS
-
TYS
Nonstop2h 32m
Allegiant Air
Sun 3/86:30 am
TYS
-
BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/10$135
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Thu 4/210:36 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Sun 4/57:30 am
TYS
-
BOS
Nonstop2h 16m
Allegiant Air
Deal found 2/9$138
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 5/2410:30 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Sat 5/306:45 am
TYS
-
BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/9$146
This Orbitz deal was found by Cheapflights users on 2/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:08 pm
BDL
-
CVG
1 stop27h 12m
Multiple Airlines
Thu 5/79:12 pm
CVG
-
BDL
Nonstop2h 02m
Multiple Airlines
Deal found 2/10$147
This Mytrip deal was found by Cheapflights users on 2/10. 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.
Thu 2/269:28 am
BOS
-
TYS
Nonstop2h 41m
Allegiant Air
Sun 3/16:30 am
TYS
-
BOS
Nonstop2h 08m
Allegiant Air
Deal found 2/10$148
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 5/239:45 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Sat 5/306:45 am
TYS
-
BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/9$152
This Mytrip deal was found by Cheapflights users on 2/10. 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.
Wed 3/115:27 am
BOS
-
BNA
1 stop15h 21m
Spirit Airlines
Wed 3/182:27 pm
BNA
-
BOS
1 stop8h 32m
Spirit Airlines
Deal found 2/10$154
This Super.com deal was found by Cheapflights users on 2/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:59 pm
BOS
-
BNA
Nonstop3h 04m
JetBlue
Wed 3/46:00 am
BNA
-
BOS
Nonstop2h 31m
JetBlue
Deal found 2/8$155
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Tue 3/109:08 am
BOS
-
BNA
Nonstop3h 04m
JetBlue
Thu 3/126:00 am
BNA
-
BOS
Nonstop2h 33m
JetBlue
Deal found 2/8$156

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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$122
(Kiwi.com)

One-way from

$75
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$405

Good round-trip deal

$347 or less

Good one-way deal

$268 or less
Provider with most accurate pricing for Boston Logan Intl-Louisville Intl flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Louisville Intl flights.
From Massachusetts to Kentucky
One-way flight from Massachusetts to Kentucky
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in February 2026
Price to beat on a round-trip flight from Massachusetts to Kentucky.
Price to beat on a one-way flight from Massachusetts to Kentucky.

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 February 11, 2026.
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 4/2

10:36 am-1:05 pm

Nonstop2h 29m

Knoxville McGhee Tyson

Sun 4/5

7:30 am-9:46 am

Nonstop2h 16m

$138

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 2/28

8:07 am-10:20 am

Nonstop3h 13m

Nashville Intl

Tue 3/3

5:45 pm-9:16 pm

Nonstop2h 31m

$157

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Tue 3/10

8:20 am-10:15 am

Nonstop2h 55m

Nashville Intl

Tue 3/17

7:35 pm-11:00 pm

Nonstop2h 25m

$162

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 3/7

5:45 am-9:22 am

1 stop4h 37m

Nashville Intl

Thu 3/12

8:00 am-3:16 pm

1 stop6h 16m

$177

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Thu 2/26

8:07 am-10:20 am

Nonstop3h 13m

Nashville Intl

Sat 2/28

3:30 pm-7:04 pm

Nonstop2h 34m

$177

HartfordCincinnati

BDL - CVG

BDLCVG

Hartford Bradley Intl

Tue 2/24

9:49 am-9:25 pm

1 stop11h 36m

Cincinnati Cinci./N. Kentucky

Sat 2/28

11:15 am-8:20 pm

1 stop9h 05m

$181

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 3/7

5:15 am-9:25 am

1 stop5h 10m

Nashville Intl

Mon 3/9

9:20 pm-12:45 am

Nonstop2h 25m

$187

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Tue 2/24

7:45 am-12:28 pm

1 stop5h 43m

Nashville Intl

Wed 3/4

7:30 am-5:21 pm

2 stops8h 51m

$187

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Wed 4/1

2:37 pm-6:56 pm

1 stop5h 19m

Nashville Intl

Wed 4/8

7:25 am-2:48 pm

1 stop6h 23m

$187

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Tue 3/17

8:55 pm-10:57 pm

Nonstop3h 02m

Nashville Intl

Fri 3/20

6:00 am-9:33 am

Nonstop2h 33m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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 $196). 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 February 11, 2026.

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.

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 February 11, 2026.
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.

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

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 popular is this Massachusetts to Kentucky flight route?

  • How long is the flight from Massachusetts to Kentucky?

    Airlines like Allegiant Air, Delta, and Southwest fly from Massachusetts to Kentucky in about 2h 29m. 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 $196). 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.

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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$243FlexibilityNo cancel feeOn-time65%
DeltaCheapest$209Average$392FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$424FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$248Average$406FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$310Average$398FlexibilityNo cancel feeOn-time63%

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