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Massachusetts

$61+ 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 1/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 3, 2025.

This JetBlue deal was found by Cheapflights users on 10/31. 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.
Wed 12/109:46 amBNA - BOS
Nonstop2h 29mJetBlue
Wed 12/103:45 pmBOS - BNA
Nonstop3h 04mJetBlue
Deal found 10/31$122
This Flysmarter deal was found by Cheapflights users on 11/1. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/49:46 amBNA - BOS
Nonstop2h 29mJetBlue
Sun 12/77:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 11/1$124
This Trip.com deal was found by Cheapflights users on 11/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/46:50 pmBNA - BOS
Nonstop2h 33mJetBlue
Mon 12/83:45 pmBOS - BNA
Nonstop3h 04mJetBlue
Deal found 11/1$125
This Trip.com deal was found by Cheapflights users on 11/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:50 pmBNA - BOS
Nonstop2h 33mJetBlue
Fri 12/123:45 pmBOS - BNA
Nonstop3h 04mJetBlue
Deal found 11/1$126
This Delta deal was found by Cheapflights users on 11/1. 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
Fri 12/127:44 pmBOS - BNA
Nonstop3h 08mDelta
Deal found 11/1$127
This JetBlue deal was found by Cheapflights users on 10/31. 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.
Thu 12/119:46 amBNA - BOS
Nonstop2h 29mJetBlue
Thu 12/113:45 pmBOS - BNA
Nonstop3h 04mJetBlue
Deal found 10/31$132
This Booking.com deal was found by Cheapflights users on 11/2. 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.
Thu 12/48:55 pmCVG - BDL
1 stop15h 29mFrontier
Sun 12/72:03 pmBDL - CVG
1 stop20h 49mFrontier
Deal found 11/2$135
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 12/182:10 pmBNA - BOS
1 stop7h 20mSouthwest
Wed 12/316:00 pmBOS - BNA
Nonstop2h 55mSouthwest
Deal found 11/2$136
This JetBlue deal was found by Cheapflights users on 10/31. 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.
Mon 12/86:50 pmBNA - BOS
Nonstop2h 33mJetBlue
Wed 12/107:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 10/31$137
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 12/187:45 pmBNA - BOS
Nonstop2h 30mSouthwest
Sat 1/38:05 pmBOS - BNA
Nonstop2h 55mSouthwest
Deal found 11/2$141
This JetBlue deal was found by Cheapflights users on 10/31. 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 12/91:10 pmBNA - BOS
1 stop5h 57mJetBlue
Wed 12/107:00 amBOS - BNA
Nonstop3h 01mJetBlue
Deal found 10/31$142
This Southwest deal was found by Cheapflights users on 10/31. 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.
Fri 11/147:45 pmBNA - BOS
Nonstop2h 30mSouthwest
Mon 11/175:35 pmBOS - BNA
1 stop4h 30mSouthwest
Deal found 10/31$147

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 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$104
(Cheapflightsfares)

One-way from

$61
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$359

Good round-trip deal

$516 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. 1% potential increase in price ($6 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 3, 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 12/12

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Tue 12/16

7:00 am-9:01 am

Nonstop3h 01m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 12/9

7:05 am-10:53 am

Nonstop2h 48m

Boston Logan Intl

Fri 12/12

7:44 pm-9:52 pm

Nonstop3h 08m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 12/2

7:00 am-10:28 am

Nonstop2h 28m

Boston Logan Intl

Thu 12/4

7:00 am-9:01 am

Nonstop3h 01m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 12/2

6:30 pm-10:02 pm

Nonstop2h 32m

Boston Logan Intl

Thu 12/4

3:34 pm-5:37 pm

Nonstop3h 03m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/5

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Fri 12/12

3:45 pm-5:49 pm

Nonstop3h 04m

$127

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Tue 12/9

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Tue 12/16

3:45 pm-5:49 pm

Nonstop3h 04m

$127

CincinnatiHartford

CVG - BDL

CVGBDL

Cincinnati Cinci./N. Kentucky

Thu 12/4

8:55 pm-12:24 pm

1 stop15h 29m

Hartford Bradley Intl

Sun 12/7

2:03 pm-10:52 am

1 stop20h 49m

$135

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/5

6:40 pm-10:15 pm

Nonstop2h 35m

Boston Logan Intl

Sun 12/7

6:55 pm-11:20 pm

1 stop5h 25m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Fri 12/5

3:55 pm-10:15 pm

1 stop5h 20m

Boston Logan Intl

Mon 12/8

8:30 am-10:20 am

Nonstop2h 50m

$137

NashvilleBoston

BNA - BOS

BNABOS

Nashville Intl

Sat 11/15

7:05 am-10:44 am

Nonstop2h 39m

Boston Logan Intl

Tue 11/18

2:54 pm-4:51 pm

Nonstop2h 57m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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 $265). 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 3, 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 3, 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
4,240 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,997 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
11,034 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,120 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

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?

    JetBlue, Delta, and Frontier can get you from Kentucky to Massachusetts in just under 2h 33m. Your travel time can differ by up to 12h 56m. There are 941 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 Allegiant Air. According to our data, you can fly for as low as $61. Users have also found prices from $69 and $69 on United Airlines and Southwest, 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 $265). 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 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 3, 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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