Massachusetts

$46+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Apr 22 — Apr 291
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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 March 23, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/21. 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.
Sat 4/186:00 am
TYS
-
BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/21$91
This Gotogate deal was found by Cheapflights users on 3/19. 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.
Thu 4/96:00 am
TYS
-
BOS
Nonstop2h 16m
Allegiant Air
Sun 4/269:06 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/19$93
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Sun 4/196:00 am
TYS
-
BOS
Nonstop2h 16m
Allegiant Air
Sun 4/269:06 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/20$98
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Thu 4/96:00 am
TYS
-
BOS
Nonstop2h 16m
Allegiant Air
Sun 4/129:06 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/18$114
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Sun 5/317:30 am
TYS
-
BOS
Nonstop2h 10m
Allegiant Air
Thu 6/410:38 am
BOS
-
TYS
Nonstop2h 23m
Allegiant Air
Deal found 3/20$131
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 4/126:00 am
TYS
-
BOS
Nonstop2h 16m
Allegiant Air
Sun 4/269:06 am
BOS
-
TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/18$146
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Thu 3/267:30 am
TYS
-
BOS
Nonstop2h 10m
Allegiant Air
Sun 3/2910:30 am
BOS
-
TYS
Nonstop2h 32m
Allegiant Air
Deal found 3/18$149
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Sat 4/186:00 am
TYS
-
BOS
Nonstop2h 16m
Multiple Airlines
Sat 4/2510:26 pm
BOS
-
TYS
1 stop17h 15m
Multiple Airlines
Deal found 3/21$151
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/196:00 am
TYS
-
BOS
Nonstop2h 16m
Multiple Airlines
Sun 4/266:30 am
BOS
-
TYS
1 stop9h 11m
Multiple Airlines
Deal found 3/21$153
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Fri 8/145:23 pm
BNA
-
ALB
Nonstop2h 09m
Allegiant Air
Mon 8/179:22 pm
ALB
-
BNA
Nonstop2h 19m
Allegiant Air
Deal found 3/21$155
This Priceline deal was found by Cheapflights users on 3/18. 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.
Wed 4/18:40 pm
BNA
-
BOS
Nonstop2h 33m
Multiple Airlines
Wed 4/89:45 am
BOS
-
BNA
1 stop11h 01m
Multiple Airlines
Deal found 3/18$158
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Tue 4/72:27 pm
BNA
-
BOS
1 stop8h 32m
Spirit Airlines
Wed 4/89:45 am
BOS
-
BNA
1 stop11h 01m
Spirit Airlines
Deal found 3/20$161

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$91
(Cheapflightsfares)

One-way from

$46
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$453

Good round-trip deal

$433 or less

Good one-way deal

$278 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. 8% potential increase in price ($35 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in March 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 March 23, 2026.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Sat 4/11

8:00 pm-11:33 pm

Nonstop2h 33m

Boston Logan Intl

Tue 4/14

7:45 pm-9:42 pm

Nonstop2h 57m

$237

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Sun 5/31

5:15 am-10:35 am

1 stop4h 20m

Hartford Bradley Intl

Sun 5/31

6:45 pm-11:00 pm

1 stop5h 15m

$237

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Sat 5/30

4:25 pm-10:55 pm

1 stop5h 30m

Hartford Bradley Intl

Sun 5/31

6:45 pm-11:00 pm

1 stop5h 15m

$237

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Sat 6/6

5:50 am-12:05 pm

1 stop5h 15m

Hartford Bradley Intl

Sun 6/7

6:25 pm-11:55 pm

1 stop6h 30m

$237

NashvilleAlbany

BNA - ALB

BNAALB

Nashville Intl

Wed 6/17

6:40 am-11:47 am

1 stop4h 07m

Albany Intl

Wed 6/24

6:00 am-9:04 am

1 stop4h 04m

$241

NashvilleAlbany

BNA - ALB

BNAALB

Nashville Intl

Mon 7/6

7:40 am-3:26 pm

1 stop6h 46m

Albany Intl

Wed 7/8

6:00 am-9:29 am

1 stop4h 29m

$241

NashvilleAlbany

BNA - ALB

BNAALB

Nashville Intl

Sat 4/18

4:13 pm-11:59 pm

1 stop6h 46m

Albany Intl

Sat 4/25

1:10 pm-6:24 pm

1 stop6h 14m

$241

NashvilleAlbany

BNA - ALB

BNAALB

Nashville Intl

Mon 7/6

6:30 pm-11:47 pm

1 stop4h 17m

Albany Intl

Tue 7/7

6:10 am-10:34 am

1 stop5h 24m

$241

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Wed 6/3

12:40 pm-10:05 pm

2 stops8h 25m

Hartford Bradley Intl

Tue 6/9

4:30 pm-10:55 pm

1 stop7h 25m

$242

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 5/28

2:45 pm-6:15 pm

Nonstop2h 30m

Boston Logan Intl

Mon 6/1

5:30 am-10:40 am

1 stop6h 10m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 60 resultsSorted by cheapest first
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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 February is currently the most expensive (average of $282). 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 March 23, 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.

Weekly flight availability from Kentucky to Massachusetts

Explore weekly flight availability from Kentucky to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 23, 2026.

The most flights from USKY to USMA are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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 March 23, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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?

    Allegiant Air, JetBlue, and Southwest can get you from Kentucky to Massachusetts in just under 2h 09m. Your travel time can differ by up to 3h 21m. There are 824 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 American Airlines. According to our data, you can fly for as low as $117. Users have also found prices from $124 and $125 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, 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 February is currently the most expensive (average of $282). 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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$351FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$191Average$219FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$357FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$384FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$294Average$372FlexibilityNo cancel feeOn-time69%

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