HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kentucky

$42+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Kentucky with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 15, 2025.

Round-trip from

$121
(Southwest)

One-way from

$42
(Cheapflightsfares)

Popular in

May

Cheapest in

August

Average price

$409

Good round-trip deal

$347 or less

Good one-way deal

$137 or less
From Massachusetts to Kentucky
Search Deals
One-way flight from Massachusetts to Kentucky
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

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 September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 10/295:00 amBOS - BNA
Nonstop2h 45mSouthwest
Mon 11/36:40 pmBNA - BOS
Nonstop2h 35mSouthwest
Deal found 9/13$121
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Mon 11/1712:56 pmALB - BNA
Nonstop2h 30mAllegiant Air
Fri 11/2111:59 amBNA - ALB
Nonstop2h 05mAllegiant Air
Deal found 9/14$121
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/43:00 pmBOS - BNA
1 stop8h 34mSpirit Airlines
Tue 10/712:40 pmBNA - BOS
1 stop10h 19mSpirit Airlines
Deal found 9/12$125
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 10/76:16 amBOS - BNA
1 stop13h 06mSpirit Airlines
Fri 10/103:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Deal found 9/14$126
This Southwest deal was found by Cheapflights users on 9/12. 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.
Thu 11/135:00 amBOS - BNA
Nonstop2h 55mSouthwest
Sat 11/1511:10 amBNA - BOS
Nonstop2h 35mSouthwest
Deal found 9/12$128
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/153:00 pmBOS - BNA
1 stop8h 06mSpirit Airlines
Thu 10/233:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Deal found 9/15$129
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
Fri 11/72:04 pmBDL - BNA
Nonstop1h 30mSpirit Airlines
Mon 11/109:49 amBNA - BDL
Nonstop2h 20mSpirit Airlines
Deal found 9/13$129
This JetBlue deal was found by Cheapflights users on 9/12. 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.
Sat 10/44:35 pmBOS - BNA
Nonstop3h 05mJetBlue
Tue 10/77:29 pmBNA - BOS
Nonstop2h 34mJetBlue
Deal found 9/12$130
This lastminute.com deal was found by Cheapflights users on 9/13. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:20 amBOS - BNA
Nonstop3h 01mJetBlue
Tue 11/410:50 amBNA - BOS
Nonstop2h 30mJetBlue
Deal found 9/13$132
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/156:16 amBOS - BNA
1 stop13h 06mSpirit Airlines
Wed 10/225:05 amBNA - BOS
1 stop7h 15mSpirit Airlines
Deal found 9/15$133
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:16 amBOS - BNA
1 stop13h 06mSpirit Airlines
Tue 10/215:05 amBNA - BOS
1 stop7h 15mSpirit Airlines
Deal found 9/14$134
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/29:28 amBOS - BNA
1 stop11h 01mMultiple Airlines
Tue 10/75:05 amBNA - BOS
1 stop7h 15mMultiple Airlines
Deal found 9/12$135

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 September 15, 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

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 11/15

9:05 am-11:04 am

Nonstop2h 59m

Nashville Intl

Mon 11/17

5:50 pm-9:29 pm

Nonstop2h 39m

$137

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Thu 10/23

5:00 am-6:45 am

Nonstop2h 45m

Nashville Intl

Mon 10/27

7:55 pm-11:25 pm

Nonstop2h 30m

$137

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Wed 11/12

7:05 am-9:06 am

Nonstop3h 01m

Nashville Intl

Mon 11/17

7:15 am-10:43 am

Nonstop2h 28m

$137

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 11/1

5:10 pm-7:20 pm

Nonstop3h 10m

Nashville Intl

Mon 11/3

11:00 am-2:42 pm

Nonstop2h 42m

$137

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 11/1

6:00 am-8:01 am

Nonstop3h 01m

Nashville Intl

Mon 11/3

6:50 pm-10:23 pm

Nonstop2h 33m

$137

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sun 11/9

7:50 am-9:52 am

Nonstop3h 02m

Nashville Intl

Thu 11/13

5:50 pm-9:29 pm

Nonstop2h 39m

$139

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Tue 11/4

2:45 pm-4:39 pm

Nonstop2h 54m

Nashville Intl

Wed 11/12

7:05 am-10:44 am

Nonstop2h 39m

$139

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Thu 11/13

5:15 am-12:15 pm

2 stops8h 00m

Nashville Intl

Sat 11/15

5:40 am-1:10 pm

1 stop6h 30m

$175

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

Tue 10/28

3:00 pm-3:36 pm

1 stop24h 36m

Knoxville McGhee Tyson

Sat 11/1

7:30 am-9:43 am

Nonstop2h 13m

$180

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Mon 10/27

5:50 pm-10:15 pm

1 stop5h 25m

Nashville Intl

Fri 10/31

4:15 pm-7:40 pm

Nonstop2h 25m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
1
2
3
...
6

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 September 15, 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 September 15, 2025.

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

How much does it cost to fly round-trip from Massachusetts to Kentucky?

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 September 15, 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
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,015 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 Delta, Southwest, and JetBlue fly from Massachusetts to Kentucky in about 2h 45m. The time it takes to get you to your destination is usually consistent. Massachusetts and Kentucky are separated by a distance of 941 mi. Most flights are nonstop.

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

    The cheapest airline one-way is Allegiant Air, with whom users have recently found tickets for as low as $60. However, be on the lookout for offers from Frontier 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, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to Las Vegas flights
San Francisco to John F Kennedy Intl flights
Los Angeles to Seattle flights
LaGuardia to Dallas/Fort Worth flights
Dallas/Fort Worth to Seattle flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to Newark flights
O'Hare Intl to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Newark to Las Vegas flights
LaGuardia to O'Hare Intl flights
LaGuardia to Fort Lauderdale flights
Seattle to Las Vegas flights
O'Hare Intl to Las Vegas flights
Newark to O'Hare Intl flights
O'Hare Intl to LaGuardia flights
Newark to Miami flights
San Francisco to Las Vegas flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Orlando flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Dallas/Fort Worth flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to San Francisco flights
Seattle to Dallas/Fort Worth flights
Seattle to Los Angeles flights
Newark to Los Angeles flights
Dallas/Fort Worth to Denver flights
LaGuardia to Miami flights
Los Angeles to Honolulu flights
Los Angeles to Dallas/Fort Worth flights
Los Angeles to LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
San Francisco to Newark flights
Newark to Orlando flights
O'Hare Intl to Newark flights
Atlanta to John F Kennedy Intl flights
Dallas/Fort Worth to Los Angeles flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Sky Harbor Intl flights
Dulles Intl to Dallas/Fort Worth flights
Atlanta to Las Vegas flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$119Average$231FlexibilityNo cancel feeOn-time65%
DeltaCheapest$241Average$434FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$435FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$463FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$402FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.