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$55+ 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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
dic. 26 — ene. 21
vie. 12/26
vie. 1/2
1 adult, Economy
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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 noviembre 26, 2025.

This Booking.com deal was found by Cheapflights users on 11/24. 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.
jue. 12/259:45 amTYS - BOS
Nonstop2h 10mAllegiant Air
mar. 12/309:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 11/24$97
This Cheapflightsfares deal was found by Cheapflights users on 11/25. 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.
sáb. 12/207:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
sáb. 1/39:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 11/25$105
This Priceline deal was found by Cheapflights users on 11/24. 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.
lun. 12/156:50 pmBNA - BOS
Nonstop2h 33mJetBlue
mar. 12/167:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/24$127
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/257:05 amBNA - BOS
Nonstop2h 48mDelta
mié. 1/78:30 amBOS - BNA
Nonstop3h 10mDelta
Deal found 11/24$131
This Southwest deal was found by Cheapflights users on 11/24. 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.
mié. 12/246:40 pmBNA - BOS
Nonstop2h 35mSouthwest
mié. 12/317:20 amBOS - BNA
1 stop7h 35mSouthwest
Deal found 11/24$135
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/257:05 amBNA - BOS
Nonstop2h 48mDelta
vie. 1/98:15 pmBOS - BNA
Nonstop3h 14mDelta
Deal found 11/24$136
This Southwest deal was found by Cheapflights users on 11/24. 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.
jue. 12/2511:05 amBNA - BOS
1 stop7h 05mSouthwest
mié. 1/79:50 amBOS - BNA
Nonstop3h 00mSouthwest
Deal found 11/24$141
This JetBlue deal was found by Cheapflights users on 11/23. 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.
vie. 12/126:50 pmBNA - BOS
Nonstop2h 33mJetBlue
lun. 12/157:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/23$142
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/257:05 amBNA - BOS
Nonstop2h 48mDelta
jue. 1/88:30 amBOS - BNA
Nonstop3h 10mDelta
Deal found 11/24$151
This Delta deal was found by Cheapflights users on 11/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/177:05 amBNA - BOS
Nonstop2h 48mDelta
mié. 12/173:34 pmBOS - BNA
Nonstop3h 03mDelta
Deal found 11/26$152
This Mytrip deal was found by Cheapflights users on 11/24. 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.
sáb. 12/139:10 amBNA - BOS
1 stop13h 46mSpirit Airlines
sáb. 1/107:00 amBOS - BNA
1 stop10h 49mSpirit Airlines
Deal found 11/24$155
This Cheapflightsfares deal was found by Cheapflights users on 11/24. 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.
dom. 12/216:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
dom. 1/49:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 11/24$158

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 noviembre 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$97
(Booking.com)

One-way from

$55
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Average price

$357

Good round-trip deal

$377 or less

Good one-way deal

$258 or less
Provider with most accurate pricing for Louisville Intl-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Boston Logan Intl flights.
Search Deals
From Kentucky to Massachusetts
Search Deals
One-way flight from Kentucky to Massachusetts
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Kentucky to Massachusetts.
Search Deals
Price to beat on a one-way flight from Kentucky to Massachusetts.
Search Deals

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 noviembre 26, 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

mié. 12/24

6:40 pm-10:15 pm

Nonstop2h 35m

Boston Logan Intl

mié. 12/31

7:20 am-1:55 pm

1 stop7h 35m

$135

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

jue. 1/8

7:20 am-11:10 am

Nonstop2h 50m

Boston Logan Intl

sáb. 1/10

8:25 am-10:41 am

Nonstop3h 16m

$142

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

jue. 1/15

9:50 am-1:21 pm

Nonstop2h 31m

Boston Logan Intl

mar. 1/20

7:05 am-9:05 am

Nonstop3h 00m

$142

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

vie. 1/23

9:50 am-1:21 pm

Nonstop2h 31m

Boston Logan Intl

lun. 1/26

7:05 am-9:05 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

mar. 1/20

7:20 am-11:10 am

Nonstop2h 50m

Boston Logan Intl

dom. 1/25

8:15 pm-10:29 pm

Nonstop3h 14m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

vie. 1/23

9:25 am-11:15 pm

1 stop12h 50m

Boston Logan Intl

lun. 1/26

7:00 am-4:49 pm

1 stop10h 49m

$161

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

jue. 12/11

6:00 am-8:10 am

Nonstop2h 10m

Boston Logan Intl

jue. 12/18

9:00 am-11:31 am

Nonstop2h 31m

$177

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

mar. 12/30

6:00 am-8:10 am

Nonstop2h 10m

Boston Logan Intl

sáb. 1/3

9:00 am-11:31 am

Nonstop2h 31m

$180

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

jue. 1/29

11:06 am-8:18 pm

1 stop8h 12m

Boston Logan Intl

lun. 2/2

7:05 am-9:05 am

Nonstop3h 00m

$182

CincinnatiAlbany

CVG - ALB

CVGALB

Cincinnati Cinci./N. Kentucky

mar. 12/9

9:03 pm-9:11 am

1 stop12h 08m

Albany Intl

sáb. 12/13

7:30 pm-8:59 am

1 stop13h 29m

$193

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

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 noviembre 26, 2025.

It’s optimal to fly from Kentucky to Massachusetts in the evening. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Kentucky to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Massachusetts flight should consider departing on Monday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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

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 noviembre 26, 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
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
7.9
Good
7,999 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
9,046 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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
8,158 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

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 10 times in the past calendar month.

  • How long is the flight from Kentucky to Massachusetts?

    Southwest, Delta, and JetBlue can get you from Kentucky to Massachusetts in just under 2h 31m. Your travel time will be generally consistent. There are 941 mi between Kentucky and Massachusetts. All flights are typically nonstop.

  • 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 $55. Users have also found prices from $69 and $72 on Delta and Southwest, 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, 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.
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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 noviembre 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$166Average$341FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$174Average$215FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$366FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$385FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$284Average$445FlexibilityNo cancel feeOn-time69%

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