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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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
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 November 16, 2025.

This Rumbo deal was found by Cheapflights users on 11/14. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:46 amBNA - BOS
Nonstop2h 29mJetBlue
Sun 12/77:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/14$121
This Rumbo deal was found by Cheapflights users on 11/15. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/69:46 amBNA - BOS
Nonstop2h 29mJetBlue
Sun 12/77:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/15$123
This JetBlue deal was found by Cheapflights users on 11/16. 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.
Fri 12/126:50 pmBNA - BOS
Nonstop2h 33mJetBlue
Sun 12/147:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/16$127
This Delta deal was found by Cheapflights users on 11/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:30 pmBNA - BOS
Nonstop2h 32mDelta
Sun 12/77:50 amBOS - BNA
Nonstop3h 07mDelta
Deal found 11/14$129
This Southwest deal was found by Cheapflights users on 11/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/610:00 amBNA - BOS
1 stop5h 05mSouthwest
Sun 12/75:00 amBOS - BNA
Nonstop2h 55mSouthwest
Deal found 11/15$137
This Priceline deal was found by Cheapflights users on 11/14. 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.
Fri 12/126:50 pmBNA - BOS
Nonstop2h 33mJetBlue
Fri 12/199:13 amBOS - BNA
Nonstop3h 03mJetBlue
Deal found 11/14$141
This Southwest deal was found by Cheapflights users on 11/14. 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.
Tue 12/1611:05 amBNA - BOS
1 stop4h 30mSouthwest
Wed 12/177:20 amBOS - BNA
1 stop7h 35mSouthwest
Deal found 11/14$147
This JetBlue deal was found by Cheapflights users on 11/16. 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.
Tue 12/26:00 amBNA - BOS
1 stop8h 14mJetBlue
Wed 12/31:40 pmBOS - BNA
1 stop8h 27mJetBlue
Deal found 11/16$157
This American Airlines deal was found by Cheapflights users on 11/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:29 pmBNA - BOS
1 stop6h 04mAmerican Airlines
Mon 12/86:00 amBOS - BNA
1 stop7h 05mAmerican Airlines
Deal found 11/14$159
This Cheapflightsfares deal was found by Cheapflights users on 11/14. 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.
Thu 11/206:00 amTYS - BOS
Nonstop2h 12mAllegiant Air
Sun 11/239:02 amBOS - TYS
Nonstop2h 32mAllegiant Air
Deal found 11/14$166
This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
Thu 12/189:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 11/13$176
This Cheapflightsfares deal was found by Cheapflights users on 11/14. 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.
Thu 12/186:00 amTYS - BOS
Nonstop2h 10mAllegiant Air
Sun 12/219:00 amBOS - TYS
Nonstop2h 31mAllegiant Air
Deal found 11/14$184

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 November 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$121
(Rumbo)

One-way from

$55
(Cheapflightsfares)

Popular in

January

Cheapest in

September

Average price

$355

Good round-trip deal

$483 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 ($4 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 November 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

Fri 12/5

6:30 pm-10:02 pm

Nonstop2h 32m

Boston Logan Intl

Mon 12/8

7:44 pm-9:52 pm

Nonstop3h 08m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/12

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Mon 12/15

3:45 pm-5:49 pm

Nonstop3h 04m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/5

6:30 pm-10:02 pm

Nonstop2h 32m

Boston Logan Intl

Fri 12/12

7:44 pm-9:52 pm

Nonstop3h 08m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 1/16

9:50 am-1:20 pm

Nonstop2h 30m

Boston Logan Intl

Tue 1/20

7:00 am-9:00 am

Nonstop3h 00m

$142

NashvilleHartford

BNA - BDL

BNABDL

Nashville Intl

Thu 1/8

11:30 am-2:50 pm

Nonstop2h 20m

Hartford Bradley Intl

Mon 1/12

9:05 am-10:55 am

Nonstop2h 50m

$143

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Wed 1/14

9:50 am-1:20 pm

Nonstop2h 30m

Boston Logan Intl

Sat 1/17

7:00 am-9:00 am

Nonstop3h 00m

$147

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 1/29

11:05 am-5:13 pm

1 stop5h 08m

Boston Logan Intl

Mon 2/2

7:00 am-9:00 am

Nonstop3h 00m

$152

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Thu 3/26

11:30 am-6:14 pm

1 stop5h 44m

Boston Logan Intl

Tue 3/31

10:40 am-5:33 pm

1 stop7h 53m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 3/20

11:30 am-8:14 pm

1 stop7h 44m

Boston Logan Intl

Sun 3/29

10:40 am-5:33 pm

1 stop7h 53m

$157

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Mon 3/23

11:30 am-8:14 pm

1 stop7h 44m

Boston Logan Intl

Mon 3/30

10:40 am-5:33 pm

1 stop7h 53m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/15

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 November 16, 2025.

It’s optimal to fly from Kentucky to Massachusetts in the evening. By choosing this option you can save up to 28% 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.

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 November 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
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8,010 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
9,017 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
11,051 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
8,143 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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?

    Delta, JetBlue, and Southwest can get you from Kentucky to Massachusetts in just under 2h 20m. Your travel time will be generally consistent. There are 850 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 Frontier. According to our data, you can fly for as low as $55. Users have also found prices from $66 and $69 on Allegiant Air 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 November 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$139Average$342FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$171Average$215FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$209Average$367FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$216Average$385FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$271Average$442FlexibilityNo cancel feeOn-time69%

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