Massachusetts

$52+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Mar 5 — Mar 121
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Cheap 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 February 3, 2026.

This Breeze Airways deal was found by Cheapflights users on 1/31. 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.
Fri 6/1910:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Mon 6/227:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Deal found 1/31$118
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/156:30 am
TYS
-
BOS
Nonstop2h 09m
Allegiant Air
Sun 2/229:29 am
BOS
-
TYS
Nonstop2h 43m
Allegiant Air
Deal found 2/1$122
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 8/209:12 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Sun 8/237:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/1$127
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 8/279:12 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Sun 8/307:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/2$128
This Expedia deal was found by Cheapflights users on 2/1. 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.
Tue 3/33:33 pm
SDF
-
BOS
1 stop8h 11m
Spirit Airlines
Tue 3/105:27 am
BOS
-
SDF
1 stop9h 11m
Spirit Airlines
Deal found 2/1$129
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/267:30 am
TYS
-
BOS
Nonstop2h 10m
Allegiant Air
Thu 4/99:06 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/2$131
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
BNA
-
BOS
1 stop14h 29m
Spirit Airlines
Tue 3/105:27 am
BOS
-
BNA
1 stop26h 58m
Spirit Airlines
Deal found 2/2$137
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:30 am
BNA
-
BOS
1 stop14h 14m
Spirit Airlines
Fri 2/203:54 pm
BOS
-
BNA
1 stop26h 51m
Spirit Airlines
Deal found 2/2$138
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:54 pm
BNA
-
BOS
1 stop19h 54m
Spirit Airlines
Wed 3/46:10 pm
BOS
-
BNA
1 stop26h 38m
Spirit Airlines
Deal found 2/1$141
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
BNA
-
BOS
1 stop14h 14m
Spirit Airlines
Wed 3/45:27 am
BOS
-
BNA
1 stop15h 21m
Spirit Airlines
Deal found 2/2$144
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 6/49:12 pm
CVG
-
BDL
Nonstop2h 02m
Breeze Airways
Sun 6/77:00 am
BDL
-
CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/1$146
This lastminute.com deal was found by Cheapflights users on 2/3. 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.
Thu 2/266:00 am
BNA
-
BOS
Nonstop2h 31m
JetBlue
Sun 3/18:59 pm
BOS
-
BNA
Nonstop3h 04m
JetBlue
Deal found 2/3$148

Find flight deals from Kentucky to Massachusetts

Keep the following information in mind while searching for Kentucky to Massachusetts flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$118
(Breeze Airways)

One-way from

$66
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$383

Good round-trip deal

$452 or less

Good one-way deal

$307 or less
Provider with most accurate pricing for Louisville Intl-Boston Logan Intl flight deals.
Provider most trusted by Cheapflights users for Louisville Intl-Boston Logan Intl flights.
From Kentucky to Massachusetts
One-way flight from Kentucky to Massachusetts
Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in February 2026
Price to beat on a round-trip flight from Kentucky to Massachusetts.
Price to beat on a one-way flight from Kentucky to Massachusetts.

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 February 3, 2026.
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

Tue 2/24

7:20 am-11:08 am

Nonstop2h 48m

Boston Logan Intl

Sat 2/28

8:07 am-10:20 am

Nonstop3h 13m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 2/27

8:40 pm-12:10 am

Nonstop2h 30m

Boston Logan Intl

Tue 3/3

9:50 am-11:50 am

Nonstop3h 00m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 3/5

9:20 pm-12:45 am

Nonstop2h 25m

Boston Logan Intl

Mon 3/16

7:25 pm-9:20 pm

Nonstop2h 55m

$162

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Mon 3/2

10:50 am-9:23 am

1 stop21h 33m

Hartford Bradley Intl

Mon 3/9

8:08 pm-10:41 am

1 stop15h 33m

$184

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 4/29

6:35 pm-11:59 pm

1 stop4h 24m

Boston Logan Intl

Sat 5/2

6:00 am-12:26 pm

1 stop7h 26m

$187

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 4/30

6:34 pm-12:59 am

1 stop5h 25m

Boston Logan Intl

Sun 5/3

5:45 am-9:28 am

1 stop4h 43m

$187

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 2/19

9:05 am-4:05 pm

1 stop6h 00m

Boston Logan Intl

Mon 2/23

5:00 am-7:05 am

Nonstop3h 05m

$187

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Mon 3/23

6:34 pm-11:57 pm

1 stop4h 23m

Boston Logan Intl

Thu 3/26

5:45 am-9:21 am

1 stop4h 36m

$187

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 3/3

10:10 am-1:40 pm

Nonstop2h 30m

Boston Logan Intl

Tue 3/10

8:55 am-1:15 pm

1 stop5h 20m

$187

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 3/20

4:00 pm-10:15 pm

1 stop5h 15m

Boston Logan Intl

Mon 3/23

7:25 pm-9:20 pm

Nonstop2h 55m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

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, September is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $139). Flying from Kentucky to Massachusetts in June 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 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 February 3, 2026.

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.

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 February 3, 2026.
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.

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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 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?

  • How long is the flight from Kentucky to Massachusetts?

    Delta, Southwest, and Frontier can get you from Kentucky to Massachusetts in just under 2h 30m. Your travel time can differ by up to 19h 03m. There are 941 mi between Kentucky and Massachusetts. This flight may include one or multiple stops.

  • 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, September is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $139). Flying from Kentucky to Massachusetts in June 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

Browse thousands of different options on Cheapflights for your next trip

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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.

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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$339FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$174Average$216FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$359FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$384FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$294Average$438FlexibilityNo cancel feeOn-time69%

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