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$55+ Cheap flights from Massachusetts to Kentucky

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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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Cheap flight deals from Massachusetts to Kentucky

Keep the following information in mind while searching for Massachusetts to Kentucky flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Mytrip)

One-way from

$55
(Cheapflightsfares)

Popular in

September

Cheapest in

January

Average price

$398

Good round-trip deal

$299 or less

Good one-way deal

$158 or less
Provider with most accurate pricing for Boston Logan Intl-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Louisville Intl flights.
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From Massachusetts to Kentucky
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One-way flight from Massachusetts to Kentucky
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Massachusetts to Kentucky.
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Price to beat on a one-way flight from Massachusetts to Kentucky.
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Find flight deals from Massachusetts to Kentucky

Cheapest flights from Massachusetts to Kentucky
Explore the most affordable flight options available from Massachusetts to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/1010:20 amBOS - TYS
Nonstop2h 33mAllegiant Air
dom. 4/137:15 amTYS - BOS
Nonstop2h 15mAllegiant Air
Deal found 2/19$97
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
jue. 3/202:10 pmBOS - BNA
1 stop6h 53mSpirit Airlines
lun. 3/242:43 pmBNA - BOS
Nonstop2h 38mSpirit Airlines
Deal found 2/20$105
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/45:07 pmBOS - TYS
1 stop24h 53mMultiple Airlines
jue. 3/66:20 amTYS - BOS
Nonstop2h 12mMultiple Airlines
Deal found 2/19$137
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/1712:15 pmBOS - BNA
1 stop12h 35mMultiple Airlines
jue. 3/206:01 amBNA - BOS
2 stops23h 54mMultiple Airlines
Deal found 2/19$143
This JetBlue Airways deal was found by Cheapflights users on 2/19. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/2010:22 pmBOS - BNA
Nonstop2h 48mJetBlue
sáb. 5/248:15 pmBNA - BOS
Nonstop2h 32mJetBlue
Deal found 2/19$157
This CheapOair deal was found by Cheapflights users on 2/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1111:36 amBDL - SDF
1 stop6h 45mSpirit Airlines
jue. 3/137:16 pmSDF - BDL
1 stop15h 25mSpirit Airlines
Deal found 2/20$158
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/1111:36 amBDL - SDF
1 stop6h 45mMultiple Airlines
vie. 3/1411:03 amSDF - BDL
1 stop4h 53mMultiple Airlines
Deal found 2/19$168
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/247:30 amBDL - SDF
1 stop7h 15mBreeze Airways
vie. 3/2811:03 amSDF - BDL
1 stop4h 53mBreeze Airways
Deal found 2/19$169
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/25:00 amBOS - BNA
Nonstop3h 05mSouthwest
mié. 3/57:20 amBNA - BOS
1 stop5h 00mSouthwest
Deal found 2/19$192
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/283:55 pmBOS - BNA
Nonstop2h 54mDelta
jue. 9/410:30 amBNA - BOS
Nonstop2h 44mDelta
Deal found 2/19$217
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/511:36 amBDL - TYS
1 stop23h 25mMultiple Airlines
mié. 3/121:30 pmTYS - BDL
2 stops21h 11mMultiple Airlines
Deal found 2/19$230
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/1712:35 pmBDL - TYS
1 stop5h 01mAmerican Airlines
mié. 5/217:55 pmTYS - BDL
1 stop4h 58mAmerican Airlines
Deal found 2/19$239

Find flights from Massachusetts to Kentucky within your budget

Customize your flight search to find flights from Massachusetts to Kentucky 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 febrero 20, 2025.

Fly from

Massachusetts

Fly to

Kentucky

Route

Depart

Return

Price

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

jue. 4/10

10:20 am-12:53 pm

Nonstop2h 33m

Knoxville McGhee Tyson

dom. 4/13

7:15 am-9:30 am

Nonstop2h 15m

$97

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

jue. 3/20

2:10 pm-8:03 pm

1 stop6h 53m

Nashville Intl

lun. 3/24

2:43 pm-6:21 pm

Nonstop2h 38m

$105

BostonKnoxville

BOS - TYS

BOSTYS

Boston Logan Intl

mar. 3/4

5:07 pm-6:00 pm

1 stop24h 53m

Knoxville McGhee Tyson

jue. 3/6

6:20 am-8:32 am

Nonstop2h 12m

$137

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

lun. 3/17

12:15 pm-11:50 pm

1 stop12h 35m

Nashville Intl

jue. 3/20

6:01 am-6:55 am

2 stops23h 54m

$143

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

mar. 5/20

10:22 pm-12:10 am

Nonstop2h 48m

Nashville Intl

sáb. 5/24

8:15 pm-11:47 pm

Nonstop2h 32m

$157

HartfordLouisville

BDL - SDF

BDLSDF

Hartford Bradley Intl

mar. 3/11

11:36 am-6:21 pm

1 stop6h 45m

Louisville Intl

jue. 3/13

7:16 pm-10:41 am

1 stop15h 25m

$158

HartfordLouisville

BDL - SDF

BDLSDF

Hartford Bradley Intl

mar. 3/11

11:36 am-6:21 pm

1 stop6h 45m

Louisville Intl

vie. 3/14

11:03 am-3:56 pm

1 stop4h 53m

$168

HartfordLouisville

BDL - SDF

BDLSDF

Hartford Bradley Intl

lun. 3/24

7:30 am-2:45 pm

1 stop7h 15m

Louisville Intl

vie. 3/28

11:03 am-3:56 pm

1 stop4h 53m

$169

BostonNashville

BOS - BNA

BOSBNA

Boston Logan Intl

dom. 3/2

5:00 am-7:05 am

Nonstop3h 05m

Nashville Intl

mié. 3/5

7:20 am-1:20 pm

1 stop5h 00m

$192

HartfordKnoxville

BDL - TYS

BDLTYS

Hartford Bradley Intl

mié. 3/5

11:36 am-11:01 am

1 stop23h 25m

Knoxville McGhee Tyson

mié. 3/12

1:30 pm-10:41 am

2 stops21h 11m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Massachusetts 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.

Travel insights for flights from Massachusetts to Kentucky

Get recent, data-driven insights about flights from Massachusetts to Kentucky including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Massachusetts to Kentucky?

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $299). Flying from Massachusetts to Kentucky in April is currently the most expensive (average of $369). 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 MA to KY?

Find hourly flight availability from Massachusetts to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated febrero 20, 2025.

When flying from Massachusetts to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Kentucky by month

Plan your trip to Kentucky by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kentucky ranges from 3.1 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Kentucky when rainfall is around 3.1 in.

Temperature in Kentucky by month

Plan your trip to Kentucky by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kentucky, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated febrero 20, 2025.
Read reviews from past customers who have flown Southwest, Breeze Airways and Alaska Airlines from Massachusetts to Kentucky. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    The cheapest airline one-way is Allegiant Air, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Spirit Airlines and Frontier, as they are both options that can get you from Massachusetts to Kentucky for a low price.

  • Can I find deals for flights from Massachusetts to Kentucky that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Kentucky.

  • Can I find deals for business class flights from Massachusetts to Kentucky?

    Yes. Cheapflights offers flight deals from Massachusetts to Kentucky 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 Massachusetts to Kentucky?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $299). Flying from Massachusetts to Kentucky in April is currently the most expensive (average of $369). 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

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Alternative routes for Massachusetts to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Massachusetts to Kentucky

Discover the top 5 airlines that operate flights from Massachusetts to Kentucky. 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$165Average$241FlexibilityNo cancel feeOn-time65%
DeltaCheapest$208Average$463FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$497FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$484FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$256Average$395FlexibilityNo cancel feeOn-time63%
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