HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kentucky to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 29, 2026.

This Breeze Airways deal was found by Cheapflights users on 1/28. 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 6/510:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Fri 6/127:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Deal found 1/28$98
This Gotogate deal was found by Cheapflights users on 1/28. 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 Gotogate 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
Thu 2/199:29 am
BOS
-
TYS
Nonstop2h 43m
Allegiant Air
Deal found 1/28$116
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 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 1/26$117
This Breeze Airways deal was found by Cheapflights users on 1/28. 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 5/2910:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Mon 6/17:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Deal found 1/28$118
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/126:30 am
TYS
-
BOS
Nonstop2h 09m
Allegiant Air
Thu 2/199:29 am
BOS
-
TYS
Nonstop2h 43m
Allegiant Air
Deal found 1/27$124
This Breeze Airways deal was found by Cheapflights users on 1/28. 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.
Mon 6/110:35 am
SDF
-
BDL
Nonstop2h 10m
Breeze Airways
Fri 6/57:35 am
BDL
-
SDF
Nonstop2h 20m
Breeze Airways
Deal found 1/28$128
This Kiwi.com deal was found by Cheapflights users on 1/28. 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
Sun 3/2910:30 am
BOS
-
TYS
Nonstop2h 32m
Allegiant Air
Deal found 1/28$133
This CheapOair deal was found by Cheapflights users on 1/27. 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 2/248:52 pm
BNA
-
BOS
1 stop18h 53m
Spirit Airlines
Tue 3/35:27 am
BOS
-
BNA
1 stop15h 21m
Spirit Airlines
Deal found 1/27$137
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:30 am
TYS
-
BOS
Nonstop2h 09m
Allegiant Air
Sun 2/229:29 am
BOS
-
TYS
Nonstop2h 43m
Allegiant Air
Deal found 1/26$138
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 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
Thu 2/269:28 am
BOS
-
TYS
Nonstop2h 41m
Allegiant Air
Deal found 1/26$139
This Southwest deal was found by Cheapflights users on 1/28. 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.
Tue 3/310:10 am
BNA
-
BOS
Nonstop2h 30m
Southwest
Mon 3/97:25 pm
BOS
-
BNA
Nonstop2h 55m
Southwest
Deal found 1/28$139
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Fri 2/138:52 pm
BNA
-
BOS
1 stop21h 35m
Spirit Airlines
Mon 2/235:50 pm
BOS
-
BNA
1 stop14h 35m
Spirit Airlines
Deal found 1/28$140

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Breeze Airways)

One-way from

$44
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$388

Good round-trip deal

$491 or less

Good one-way deal

$312 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. 5% potential increase in price ($19 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 January 2026
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 January 29, 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

LouisvilleHartford

SDF - BDL

SDFBDL

Louisville Intl

Fri 6/5

10:35 am-12:45 pm

Nonstop2h 10m

Hartford Bradley Intl

Fri 6/12

7:35 am-9:55 am

Nonstop2h 20m

$98

KnoxvilleBoston

TYS - BOS

TYSBOS

Knoxville McGhee Tyson

Sun 2/15

6:30 am-8:39 am

Nonstop2h 09m

Boston Logan Intl

Thu 2/19

9:29 am-12:12 pm

Nonstop2h 43m

$116

LouisvilleHartford

SDF - BDL

SDFBDL

Louisville Intl

Mon 6/1

10:35 am-12:45 pm

Nonstop2h 10m

Hartford Bradley Intl

Fri 6/5

7:35 am-9:55 am

Nonstop2h 20m

$128

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 2/18

6:15 pm-9:45 pm

Nonstop2h 30m

Boston Logan Intl

Fri 2/20

5:20 am-7:20 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 3/17

7:05 am-10:43 am

Nonstop2h 38m

Boston Logan Intl

Tue 3/24

2:33 pm-4:35 pm

Nonstop3h 02m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 2/24

11:08 am-2:41 pm

Nonstop2h 33m

Boston Logan Intl

Fri 3/6

8:50 pm-10:54 pm

Nonstop3h 04m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 2/27

8:40 pm-12:10 am

Nonstop2h 30m

Boston Logan Intl

Sun 3/1

5:20 am-7:20 am

Nonstop3h 00m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 3/26

9:20 pm-12:45 am

Nonstop2h 25m

Boston Logan Intl

Mon 3/30

7:25 pm-9:20 pm

Nonstop2h 55m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 3/4

7:20 am-11:08 am

Nonstop2h 48m

Boston Logan Intl

Wed 3/11

12:00 pm-6:43 pm

1 stop7h 43m

$161

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 2/26

8:25 am-2:16 pm

1 stop4h 51m

Boston Logan Intl

Sun 3/8

8:03 pm-10:02 pm

Nonstop2h 59m

$172

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
1
2
3
...
6

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 January 29, 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 January 29, 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.
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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
8,393 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

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 9 times in the past calendar month.

  • How long is the flight from Kentucky to Massachusetts?

    Breeze Airways, Allegiant Air, and Southwest can get you from Kentucky to Massachusetts in just under 2h 09m. Your travel time will be generally consistent. There are 829 mi between Kentucky and Massachusetts. All flights are typically nonstop.

  • 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kentucky to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
Newark to Fort Lauderdale flights
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
San Francisco to John F Kennedy Intl flights
John F Kennedy Intl to West Palm Beach flights
Newark to West Palm Beach flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Las Vegas flights
Los Angeles to John F Kennedy Intl flights
San Francisco to Newark flights
O'Hare Intl to Sky Harbor Intl flights
Seattle to Los Angeles flights
Newark to Las Vegas flights
Seattle to Las Vegas flights
O'Hare Intl to Las Vegas flights
Newark to Orlando flights
John F Kennedy Intl to Tampa flights
Minneapolis to Sky Harbor Intl flights
Los Angeles to Seattle flights
O'Hare Intl to Dallas/Fort Worth flights
LaGuardia to Orlando flights
San Francisco to LaGuardia flights
Newark to Tampa flights
John F Kennedy Intl to San Francisco flights
LaGuardia to Tampa flights
Dallas/Fort Worth to John F Kennedy Intl flights
Boston to Fort Lauderdale flights
Newark to Los Angeles flights
San Francisco to Las Vegas flights
John F Kennedy Intl to Sky Harbor Intl flights
Dulles Intl to Miami flights
Boston to Miami flights
Reagan-National to Miami flights
Los Angeles to Honolulu flights
Dallas/Fort Worth to LaGuardia flights
Boston to Tampa flights
LaGuardia to West Palm Beach flights
Detroit to Orlando flights
Seattle to Sky Harbor Intl flights
Newark to Sky Harbor Intl flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to New Orleans flights
Dallas/Fort Worth to Las Vegas flights
Minneapolis to Orlando flights
Newark to New Orleans flights
O'Hare Intl to Fort Lauderdale flights

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$339FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$174Average$216FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$361FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$384FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$294Average$438FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.