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$64+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
يناير 15 — يناير 221
خ 1/15
خ 1/22
1 adult, Economy
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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 ديسمبر 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ح 12/216:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
خ 1/112:45 pmBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 12/14$154
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ح 12/216:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
ح 1/49:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 12/14$170
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ن 12/225:38 pmTYS - BOS
1 stop16h 23mMultiple Airlines
خ 1/112:45 pmBOS - TYS
Nonstop2h 31mMultiple Airlines
Deal found 12/14$181
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ح 12/216:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
س 1/39:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 12/14$195
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ن 12/225:38 pmTYS - BOS
1 stop16h 23mMultiple Airlines
ح 1/49:00 amBOS - TYS
Nonstop2h 31mMultiple Airlines
Deal found 12/14$199
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ث 12/306:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
ح 1/49:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 12/15$215
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ث 12/308:38 pmBNA - BOS
1 stop13h 12mSpirit Airlines
ن 1/511:55 amBOS - BNA
1 stop23h 14mSpirit Airlines
Deal found 12/15$217
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ن 12/225:38 pmTYS - BOS
1 stop16h 23mMultiple Airlines
س 1/39:00 amBOS - TYS
Nonstop2h 31mMultiple Airlines
Deal found 12/14$226
This Southwest deal was found by Cheapflights users on 12/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ج 12/264:05 pmBNA - BOS
Nonstop2h 30mSouthwest
ج 1/25:00 amBOS - BNA
Nonstop2h 55mSouthwest
Deal found 12/14$232
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ث 12/306:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
س 1/39:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 12/15$235
This Mytrip deal was found by Cheapflights users on 12/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ح 12/216:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
ح 12/289:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 12/14$236
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ج 12/269:49 amBNA - BOS
1 stop6h 55mAmerican Airlines
خ 1/17:00 amBOS - BNA
1 stop6h 41mAmerican Airlines
Deal found 12/15$237

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 ديسمبر 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$90
(Mytrip)

One-way from

$64
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$377

Good round-trip deal

$355 or less

Good one-way deal

$344 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. 1% potential increase in price ($5 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 December 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 ديسمبر 16, 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

ر 1/14

7:20 am-11:10 am

Nonstop2h 50m

Boston Logan Intl

ر 1/14

8:15 pm-10:29 pm

Nonstop3h 14m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

ن 1/12

9:50 am-1:21 pm

Nonstop2h 31m

Boston Logan Intl

ر 1/14

7:05 am-9:05 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

ح 1/11

7:20 am-11:10 am

Nonstop2h 50m

Boston Logan Intl

س 1/17

4:40 pm-6:48 pm

Nonstop3h 08m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

ن 1/12

9:50 am-1:21 pm

Nonstop2h 31m

Boston Logan Intl

ث 1/20

7:05 am-9:05 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

ج 1/9

7:20 am-11:10 am

Nonstop2h 50m

Boston Logan Intl

ن 1/12

8:15 pm-10:29 pm

Nonstop3h 14m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

خ 1/8

9:50 am-1:21 pm

Nonstop2h 31m

Boston Logan Intl

س 1/10

7:05 am-9:05 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

س 1/10

9:50 am-1:20 pm

Nonstop2h 30m

Boston Logan Intl

ح 1/18

7:05 am-9:05 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

ث 2/10

7:20 am-11:10 am

Nonstop2h 50m

Boston Logan Intl

ر 2/18

2:55 pm-4:59 pm

Nonstop3h 04m

$152

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

س 2/7

9:50 am-1:20 pm

Nonstop2h 30m

Boston Logan Intl

ث 2/17

8:53 am-10:57 am

Nonstop3h 04m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

ث 2/10

9:50 am-1:20 pm

Nonstop2h 30m

Boston Logan Intl

ث 2/17

8:53 am-10:57 am

Nonstop3h 04m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

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, 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 ديسمبر 16, 2025.

It’s optimal to fly from Kentucky to Massachusetts in the evening. By choosing this option you can save up to 26% 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. Sunday 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 ديسمبر 16, 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
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

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
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

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
Delta
7.9
Good
8,010 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

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
United Airlines
7.4
Good
9,094 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

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
American Airlines
7.2
Good
11,048 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

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
Spirit Airlines
6.3
Okay
8,186 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

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?

    Flights from Kentucky to Massachusetts have been viewed 12 times in the past calendar month.

  • How long is the flight from Kentucky to Massachusetts?

    Delta, JetBlue, and Frontier can get you from Kentucky to Massachusetts in just under 2h 31m. Your travel time can differ by up to 9h 14m. 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 United Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $117 and $129 on American Airlines and Delta, 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 ديسمبر 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$166Average$344FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$174Average$215FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$365FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$386FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$284Average$463FlexibilityNo cancel feeOn-time69%

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