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$44+ Cheap flights from Kentucky to Massachusetts

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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Kentucky to Massachusetts

Keep the following information in mind while searching for Kentucky to Massachusetts flight deals. Data was last updated September 17, 2025.

Round-trip from

$78
(Cheapflightsfares)

One-way from

$44
(Cheapflightsfares)

Popular in

April

Cheapest in

November

Average price

$343

Good round-trip deal

$275 or less

Good one-way deal

$180 or less
From Kentucky to Massachusetts
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One-way flight from Kentucky to Massachusetts
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Highest demand for flights based on searches. 2% potential increase in price ($8 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 September 2025
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Price to beat on a round-trip flight from Kentucky to Massachusetts.
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Price to beat on a one-way flight from Kentucky to Massachusetts.
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Find flight deals from Kentucky to Massachusetts

Cheapest flights from Kentucky to Massachusetts
Explore the most affordable flight options available from Kentucky to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

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.
Fri 10/246:30 amBNA - ALB
Nonstop2h 09mAllegiant Air
Mon 10/2711:29 amALB - BNA
Nonstop2h 22mAllegiant Air
Deal found 9/15$78
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Fri 9/267:00 amBNA - ALB
Nonstop2h 10mAllegiant Air
Mon 9/2911:00 amALB - BNA
Nonstop2h 21mAllegiant Air
Deal found 9/17$92
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.
Mon 9/227:00 amBNA - ALB
Nonstop2h 10mAllegiant Air
Mon 9/2911:00 amALB - BNA
Nonstop2h 21mAllegiant Air
Deal found 9/15$106
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Thu 10/163:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Mon 10/2012:49 pmBOS - BNA
Nonstop2h 47mSpirit Airlines
Deal found 9/17$117
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/63:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Mon 10/2012:49 pmBOS - BNA
Nonstop2h 47mSpirit Airlines
Deal found 9/17$118
This flygcity.se 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:45 amBNA - BOS
Nonstop2h 42mJetBlue
Mon 10/66:20 pmBOS - BNA
Nonstop3h 18mJetBlue
Deal found 9/15$121
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.
Mon 10/63:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Wed 10/86:16 amBOS - BNA
1 stop13h 06mSpirit Airlines
Deal found 9/15$126
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.
Mon 10/63:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Tue 10/76:16 amBOS - BNA
1 stop13h 06mSpirit Airlines
Deal found 9/15$129
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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.
Thu 10/233:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Sun 10/2612:49 pmBOS - BNA
Nonstop2h 47mSpirit Airlines
Deal found 9/17$131
This Jettzy 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:50 pmBNA - BOS
Nonstop2h 33mJetBlue
Mon 11/108:10 pmBOS - BNA
Nonstop3h 01mJetBlue
Deal found 9/14$134
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.
Fri 10/176:30 amBNA - ALB
Nonstop2h 09mAllegiant Air
Mon 10/2012:59 pmALB - BNA
Nonstop2h 22mAllegiant Air
Deal found 9/15$134
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Thu 10/233:41 pmBNA - BOS
Nonstop2h 35mSpirit Airlines
Tue 10/282:15 pmBOS - BNA
1 stop5h 55mSpirit Airlines
Deal found 9/16$135

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Massachusetts 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 17, 2025.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.

Fly from

Kentucky

Fly to

Massachusetts

Route

Depart

Return

Price

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 10/1

7:35 pm-11:12 pm

Nonstop2h 37m

Boston Logan Intl

Sat 10/4

4:35 pm-6:40 pm

Nonstop3h 05m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 11/12

7:05 am-10:44 am

Nonstop2h 39m

Boston Logan Intl

Wed 11/12

7:41 pm-9:57 pm

Nonstop3h 16m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Sat 10/25

7:05 am-10:48 am

Nonstop2h 43m

Boston Logan Intl

Tue 10/28

7:40 pm-9:44 pm

Nonstop3h 04m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 11/7

7:15 am-10:43 am

Nonstop2h 28m

Boston Logan Intl

Sun 11/9

8:15 pm-10:10 pm

Nonstop2h 55m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 11/6

7:15 am-10:43 am

Nonstop2h 28m

Boston Logan Intl

Sun 11/9

7:05 am-9:06 am

Nonstop3h 01m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 11/13

7:05 am-10:44 am

Nonstop2h 39m

Boston Logan Intl

Sat 11/15

4:20 pm-6:34 pm

Nonstop3h 14m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 10/16

5:07 pm-8:49 pm

Nonstop2h 42m

Boston Logan Intl

Mon 10/20

8:30 am-10:18 am

Nonstop2h 48m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 10/30

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Mon 11/3

7:20 am-9:21 am

Nonstop3h 01m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 10/1

3:08 pm-7:11 pm

Nonstop3h 03m

Boston Logan Intl

Fri 10/31

8:10 pm-10:11 pm

Nonstop3h 01m

$152

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Sat 12/13

12:45 pm-9:53 pm

1 stop8h 08m

Hartford Bradley Intl

Wed 12/17

6:00 am-2:28 pm

2 stops9h 28m

$156

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Kentucky 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 Kentucky to Massachusetts

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

Currently, January is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $218). Flying from Kentucky to Massachusetts in July is currently the most expensive (average of $311). 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 KY to MA?

Find hourly flight availability from Kentucky to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Massachusetts as you normally would.

Weekly flight availability from Kentucky to Massachusetts

Explore weekly flight availability from Kentucky to Massachusetts. 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 17, 2025.

The most flights from USKY to USMA are scheduled on a Tuesday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated September 17, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Kentucky to Massachusetts by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

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 Kentucky to Massachusetts. 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 Kentucky to Massachusetts flight route?

    Flights from Kentucky to Massachusetts have been viewed 11 times in the past calendar month.

  • How long is the flight from Kentucky to Massachusetts?

    JetBlue, Delta, and United Airlines can get you from Kentucky to Massachusetts in just under 2h 37m. Your travel time can differ by up to 5h 31m. There are 941 mi between Kentucky and Massachusetts. This flight may include one or multiple stops.

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

    For one-way options, check prices for Allegiant Air. According to our data, you can fly for as low as $61. Users have also found prices from $64 and $70 on Southwest and Spirit Airlines, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky to Massachusetts 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 Kentucky to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $218). Flying from Kentucky to Massachusetts in July is currently the most expensive (average of $311). 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 Kentucky to Massachusetts

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

Discover the top 5 airlines that operate flights from Kentucky to Massachusetts. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$166Average$342FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$171Average$216FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$366FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$397FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$268Average$445FlexibilityNo cancel feeOn-time69%

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