Massachusetts

$29+ 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
Aug 19 — Aug 261
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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 August 14, 2025.

Round-trip from

$78
(FlightHub)

One-way from

$29
(Cheapflightsfares)

Popular in

October

Cheapest in

November

Average price

$342

Good round-trip deal

$289 or less

Good one-way deal

$222 or less
From Kentucky to Massachusetts
One-way flight from Kentucky to Massachusetts
High demand for flights, 0% potential price rise
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in August 2025
Price to beat on a round-trip flight from Kentucky to Massachusetts.
Price to beat on a one-way flight from Kentucky to Massachusetts.

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 August 14, 2025.

This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/318:28 amBNA - BDL
Nonstop2h 21mSpirit Airlines
Mon 11/312:54 pmBDL - BNA
Nonstop2h 24mSpirit Airlines
Deal found 8/14$78
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 10/169:48 pmBNA - BDL
1 stop11h 47mSpirit Airlines
Mon 10/201:00 pmBDL - BNA
Nonstop2h 20mSpirit Airlines
Deal found 8/12$95
This Cheapflightsfares deal was found by Cheapflights users on 8/11. 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 8/296:45 amBNA - BDL
Nonstop2h 20mSpirit Airlines
Mon 9/15:17 pmBDL - BNA
Nonstop2h 20mSpirit Airlines
Deal found 8/11$99
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:34 pmBNA - BDL
Nonstop2h 19mSpirit Airlines
Mon 9/2211:30 amBDL - BNA
1 stop12h 04mSpirit Airlines
Deal found 8/11$104
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/243:17 pmBNA - BOS
Nonstop2h 43mSpirit Airlines
Mon 10/2712:20 pmBOS - BNA
Nonstop2h 52mSpirit Airlines
Deal found 8/14$108
This FlightHub deal was found by Cheapflights users on 8/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/99:26 pmBNA - BDL
1 stop12h 04mSpirit Airlines
Mon 10/1312:54 pmBDL - BNA
Nonstop2h 24mSpirit Airlines
Deal found 8/13$114
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1511:38 amBNA - BDL
1 stop7h 19mMultiple Airlines
Fri 9/195:58 pmBDL - BNA
Nonstop2h 26mMultiple Airlines
Deal found 8/14$115
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/72:18 pmBNA - BOS
Nonstop2h 44mSpirit Airlines
Fri 11/146:57 pmBOS - BNA
Nonstop2h 55mSpirit Airlines
Deal found 8/14$118
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Tue 9/94:50 pmBNA - BOS
1 stop6h 07mSpirit Airlines
Tue 9/163:00 pmBOS - BNA
1 stop8h 34mSpirit Airlines
Deal found 8/13$121
This Mytrip deal was found by Cheapflights users on 8/12. 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.
Fri 9/51:34 pmBNA - BDL
Nonstop2h 19mSpirit Airlines
Mon 9/811:30 amBDL - BNA
1 stop12h 04mSpirit Airlines
Deal found 8/12$123
This Kissandfly.com deal was found by Cheapflights users on 8/13. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:35 pmBNA - BOS
Nonstop2h 37mJetBlue
Sun 10/58:00 amBOS - BNA
Nonstop2h 50mJetBlue
Deal found 8/13$127
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:34 pmBNA - BDL
Nonstop2h 19mMultiple Airlines
Sun 9/148:37 pmBDL - BNA
1 stop15h 16mMultiple Airlines
Deal found 8/14$129

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 August 14, 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

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Fri 10/31

8:28 am-11:49 am

Nonstop2h 21m

Hartford Bradley Intl

Mon 11/3

12:54 pm-2:18 pm

Nonstop2h 24m

$78

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Fri 9/19

1:34 pm-4:53 pm

Nonstop2h 19m

Hartford Bradley Intl

Mon 9/22

5:58 pm-7:24 pm

Nonstop2h 26m

$78

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Fri 9/12

1:34 pm-4:53 pm

Nonstop2h 19m

Hartford Bradley Intl

Fri 9/19

5:58 pm-7:24 pm

Nonstop2h 26m

$78

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Thu 10/16

9:48 pm-10:35 am

1 stop11h 47m

Hartford Bradley Intl

Mon 10/20

1:00 pm-2:20 pm

Nonstop2h 20m

$95

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Fri 8/29

6:45 am-10:05 am

Nonstop2h 20m

Hartford Bradley Intl

Mon 9/1

5:17 pm-6:37 pm

Nonstop2h 20m

$99

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 10/23

3:17 pm-7:00 pm

Nonstop2h 43m

Boston Logan Intl

Sun 10/26

12:20 pm-2:12 pm

Nonstop2h 52m

$108

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 10/16

3:17 pm-7:00 pm

Nonstop2h 43m

Boston Logan Intl

Mon 10/20

12:20 pm-2:12 pm

Nonstop2h 52m

$108

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 10/24

3:17 pm-7:00 pm

Nonstop2h 43m

Boston Logan Intl

Mon 10/27

12:20 pm-2:12 pm

Nonstop2h 52m

$108

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 10/24

3:41 pm-7:16 pm

Nonstop2h 35m

Boston Logan Intl

Sun 10/26

12:49 pm-2:36 pm

Nonstop2h 47m

$108

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Thu 10/9

9:26 pm-10:30 am

1 stop12h 04m

Hartford Bradley Intl

Mon 10/13

12:54 pm-2:18 pm

Nonstop2h 24m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

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 August 14, 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.

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 August 14, 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.

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
8.0
Very good

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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?

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $29. Users have also found prices from $79 and $81 on Delta and United 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

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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$166Average$366FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$171Average$216FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$376FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$382FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$268Average$445FlexibilityNo cancel feeOn-time69%

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