Kentucky

$39+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Jun 20 — Jun 271
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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 May 21, 2026.

This Super.com deal was found by Cheapflights users on 5/17. 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.
Thu 5/287:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Tue 6/28:40 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17$147
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 7/49:40 am
BOS
-
TYS
Nonstop2h 22m
Allegiant Air
Thu 7/97:30 am
TYS
-
BOS
Nonstop2h 20m
Allegiant Air
Deal found 5/16$149
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 5/16$150
This Cheapflightsfares deal was found by Cheapflights users on 5/16. 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.
Sat 8/19:55 am
BOS
-
TYS
Nonstop2h 22m
Allegiant Air
Sat 8/86:45 am
TYS
-
BOS
Nonstop2h 20m
Allegiant Air
Deal found 5/16$151
This Breeze Airways deal was found by Cheapflights users on 5/19. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Sun 6/148:40 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/19$153
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Sat 6/69:53 am
BOS
-
TYS
Nonstop2h 23m
Allegiant Air
Sat 6/136:45 am
TYS
-
BOS
Nonstop2h 18m
Allegiant Air
Deal found 5/18$155
This Cheapflightsfares deal was found by Cheapflights users on 5/17. 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.
Sat 6/69:53 am
BOS
-
TYS
Nonstop2h 23m
Allegiant Air
Sat 6/206:30 am
TYS
-
BOS
Nonstop2h 18m
Allegiant Air
Deal found 5/17$157
This Super.com deal was found by Cheapflights users on 5/16. 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.
Sun 5/247:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Sun 5/318:40 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/16$157
This Mytrip deal was found by Cheapflights users on 5/20. 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 8/2012:39 pm
BOS
-
TYS
Nonstop2h 28m
Allegiant Air
Sun 8/239:30 am
TYS
-
BOS
Nonstop2h 19m
Allegiant Air
Deal found 5/20$159
This Flightnetwork deal was found by Cheapflights users on 5/18. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:40 am
BOS
-
TYS
Nonstop2h 22m
Allegiant Air
Sun 7/57:30 am
TYS
-
BOS
Nonstop2h 20m
Allegiant Air
Deal found 5/18$162
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 5/287:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Thu 6/48:40 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17$162
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 5/16$163

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 May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$149
(Kiwi.com)

One-way from

$39
(Kiwi.com)

Popular in

April

Cheapest in

August

Average price

$470

Good round-trip deal

$446 or less

Good one-way deal

$273 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. 13% potential increase in price ($66 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in May 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 May 21, 2026.
Use the filters below to find and compare flights from Massachusetts to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

Sat 6/6

5:10 am-9:30 am

1 stop5h 20m

Nashville Intl

Sat 6/13

12:50 pm-4:20 pm

Nonstop2h 30m

$237

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Wed 7/29

6:00 am-10:09 am

1 stop5h 09m

Nashville Intl

Sun 8/2

6:05 am-11:45 am

1 stop4h 40m

$241

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Wed 7/29

6:00 am-11:30 am

1 stop6h 30m

Nashville Intl

Sat 8/1

5:40 pm-11:21 pm

1 stop4h 41m

$241

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Thu 8/20

6:05 pm-10:10 pm

1 stop5h 05m

Nashville Intl

Tue 8/25

11:15 am-5:30 pm

1 stop5h 15m

$241

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Wed 7/8

4:15 pm-8:40 pm

1 stop5h 25m

Nashville Intl

Tue 7/14

6:50 am-12:15 pm

1 stop4h 25m

$241

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Tue 7/28

5:45 am-12:00 pm

1 stop7h 15m

Nashville Intl

Sun 8/2

5:10 am-11:25 am

1 stop5h 15m

$241

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Wed 7/29

9:15 am-2:00 pm

1 stop5h 45m

Nashville Intl

Sun 8/2

5:15 am-12:25 pm

1 stop6h 10m

$241

HartfordNashville

BDL - BNA

BDLBNA

Hartford Bradley Intl

Wed 8/12

3:05 pm-7:55 pm

2 stops5h 50m

Nashville Intl

Tue 8/18

8:50 am-2:50 pm

1 stop5h 00m

$242

AlbanyNashville

ALB - BNA

ALBBNA

Albany Intl

Fri 9/11

1:15 pm-6:40 pm

2 stops6h 25m

Nashville Intl

Mon 9/14

5:25 am-12:40 pm

1 stop6h 15m

$246

HartfordNashville

BDL - BNA

BDLBNA

Hartford Bradley Intl

Fri 7/3

3:02 pm-6:47 pm

1 stop4h 45m

Nashville Intl

Tue 7/7

6:00 am-2:06 pm

2 stops7h 06m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $98). Flying from Massachusetts to Kentucky in March is currently the most expensive (average of $275). 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 May 21, 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.

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

How far ahead should I book a flight from Massachusetts to Kentucky?

The best time to book flights from Massachusetts to Kentucky is 34 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 May 21, 2026.
See what other customers who have flown with Southwest,Delta, andUnited 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

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

7.9

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 Breeze Airways, Southwest, and Delta fly from Massachusetts to Kentucky in about 2h 07m. The time it takes to get you to your destination can typically vary by up to 3h 13m. Massachusetts and Kentucky are separated by a distance of 659 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Southwest, 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 $98). Flying from Massachusetts to Kentucky in March is currently the most expensive (average of $275). 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.

Top 4 airlines flying from Massachusetts to Kentucky

Discover the top 4 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 May 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$248Average$508FlexibilityNo cancel feeOn-time69%
DeltaCheapest$248Average$397FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$403FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$335Average$479FlexibilityNo cancel feeOn-time63%

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