$43+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Sep 14 — Sep 211
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Kentucky to MassachusettsExplore 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 15, 2026.
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 15, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:20 am -
Nonstop2h 09m
Mon 9/1412:39 pm -
Nonstop2h 18m
Deal found 8/14![Allegiant Air logo]()
$83
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/2112:39 pm -
Nonstop2h 18m
Deal found 8/13![Allegiant Air logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Mon 8/2410:35 am -
Nonstop2h 10m
Fri 9/47:35 am -
Nonstop2h 20m
Deal found 8/10![Breeze Airways logo]()
$113
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:35 am -
Nonstop2h 10m
Fri 8/287:35 am -
Nonstop2h 20m
Deal found 8/11![Breeze Airways logo]()
$128
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:35 am -
Nonstop2h 10m
Mon 9/77:35 am -
Nonstop2h 20m
Deal found 8/11![Breeze Airways logo]()
$133
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 10/316:00 am -
Nonstop2h 12m
Sun 11/110:32 am -
Nonstop2h 30m
Deal found 8/10![Allegiant Air logo]()
$135
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:30 am -
Nonstop2h 09m
Mon 8/3110:59 am -
Nonstop2h 21m
Deal found 8/12![Allegiant Air logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 10/117:15 am -
Nonstop2h 12m
Tue 10/2011:32 am -
Nonstop2h 30m
Deal found 8/10![Allegiant Air logo]()
$143
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/2812:39 pm -
Nonstop2h 18m
Deal found 8/13![Allegiant Air logo]()
$145
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.
Fri 8/218:30 am -
Nonstop2h 09m
Mon 8/2412:29 pm -
Nonstop2h 21m
Deal found 8/12![Allegiant Air logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 9/199:30 am -
Nonstop2h 15m
Sat 9/2612:35 pm -
Nonstop2h 26m
Deal found 8/10![Allegiant Air logo]()
$157
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.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/288:18 pm -
2 stops37h 30m
Deal found 8/13![Multiple Airlines logo]()
$161
Best flights from Kentucky to MassachusettsDiscover carefully curated flight deals from Kentucky to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
Discover carefully curated flight deals from Kentucky to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 15, 2026.
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/203:05 pm -
2 stops7h 54m
Sat 10/249:44 am -
1 stop5h 36m
Deal found 8/10![United Airlines logo]()
$202
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:35 pm -
Nonstop2h 42m
Mon 10/57:50 pm -
Nonstop2h 54m
Deal found 8/12![Delta logo]()
$219
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:20 pm -
Nonstop2h 30m
Fri 10/306:05 pm -
Nonstop2h 45m
Deal found 8/13![Southwest logo]()
$248
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:25 pm -
1 stop7h 49m
Mon 9/287:00 am -
1 stop7h 28m
Deal found 8/13![JetBlue logo]()
$263
This American Airlines deal was found by Cheapflights users on 8/10. 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.
Sun 9/136:11 pm -
1 stop5h 15m
Fri 9/185:50 pm -
1 stop5h 00m
Deal found 8/10![American Airlines logo]()
$367
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:00 pm -
Nonstop2h 50m
Wed 9/96:55 pm -
Nonstop2h 56m
Deal found 8/13![Delta logo]()
$219
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:02 am -
2 stops7h 03m
Sun 9/276:00 am -
1 stop4h 31m
Deal found 8/11![United Airlines logo]()
$234
This Southwest deal was found by Cheapflights users on 8/10. 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 10/225:10 pm -
2 stops5h 55m
Tue 10/275:35 am -
2 stops6h 55m
Deal found 8/10![Southwest logo]()
$251
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:33 pm -
1 stop5h 37m
Sun 9/205:45 am -
1 stop4h 49m
Deal found 8/13![United Airlines logo]()
$239
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:10 pm -
1 stop6h 40m
Sat 11/147:25 am -
1 stop5h 30m
Deal found 8/11![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 8/10. 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.
Wed 9/166:28 pm -
1 stop5h 29m
Mon 9/216:23 pm -
1 stop6h 00m
Deal found 8/10![Delta logo]()
$257
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:00 am -
Nonstop2h 34m
Wed 10/71:00 pm -
1 stop6h 36m
Deal found 8/14![JetBlue logo]()
$288
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:15 am -
1 stop5h 19m
Tue 9/2212:12 pm -
1 stop8h 20m
Deal found 8/13![United Airlines logo]()
$257
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:10 am -
2 stops8h 30m
Sat 10/175:40 am -
1 stop6h 40m
Deal found 8/11![Southwest logo]()
$263
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:23 pm -
1 stop5h 27m
Tue 10/135:50 am -
1 stop5h 12m
Deal found 8/12![Delta logo]()
$271
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:10 am -
2 stops6h 55m
Sat 9/1211:45 am -
1 stop7h 22m
Deal found 8/13![United Airlines logo]()
$263
This Southwest deal was found by Cheapflights users on 8/10. 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.
Wed 9/95:40 am -
2 stops9h 55m
Wed 9/1612:50 pm -
1 stop7h 25m
Deal found 8/10![Southwest logo]()
$264
This Delta deal was found by Cheapflights users on 8/10. 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.
Thu 9/36:00 am -
1 stop6h 47m
Sun 9/66:00 am -
1 stop4h 09m
Deal found 8/10![Delta logo]()
$275
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:25 pm -
1 stop7h 49m
Sat 9/197:00 am -
1 stop7h 28m
Deal found 8/12![JetBlue logo]()
$339
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:18 am -
1 stop6h 02m
Sun 8/306:00 am -
2 stops7h 35m
Deal found 8/11![United Airlines logo]()
$266
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:00 pm -
1 stop4h 05m
Sat 10/175:35 am -
1 stop4h 45m
Deal found 8/11![Southwest logo]()
$272
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:40 am -
1 stop5h 28m
Sun 9/205:30 am -
1 stop5h 48m
Deal found 8/12![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:30 am -
2 stops7h 19m
Sat 12/125:04 pm -
1 stop6h 51m
Deal found 8/15![United Airlines logo]()
$276
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:05 am -
Nonstop2h 30m
Mon 10/197:30 pm -
Nonstop2h 45m
Deal found 8/12![Southwest logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:56 am -
1 stop5h 15m
Sun 9/65:42 am -
1 stop7h 20m
Deal found 8/15![American Airlines logo]()
$467
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:30 am -
1 stop5h 59m
Tue 9/86:10 am -
2 stops10h 47m
Deal found 8/13![United Airlines logo]()
$282
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:55 am -
1 stop6h 34m
Sat 11/78:00 am -
1 stop6h 49m
Deal found 8/13![Delta logo]()
$319
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:45 pm -
1 stop4h 35m
Tue 9/110:05 am -
2 stops8h 50m
Deal found 8/11![Southwest logo]()
$298
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:54 pm -
1 stop4h 35m
Sat 10/245:30 am -
1 stop6h 38m
Deal found 8/14![Delta logo]()
$319
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:00 am -
2 stops7h 07m
Sat 10/3112:40 pm -
1 stop8h 12m
Deal found 8/14![United Airlines logo]()
$294
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated August 15, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated August 15, 2026 and is based on user searches.
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.
Fri 8/218:30 am -
Nonstop2h 09m
Mon 8/2412:29 pm -
Nonstop2h 21m
Deal found 8/12![Allegiant Air logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Mon 8/2410:35 am -
Nonstop2h 10m
Fri 9/47:35 am -
Nonstop2h 20m
Deal found 8/10![Breeze Airways logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Mon 8/2410:35 am -
Nonstop2h 10m
Mon 8/317:35 am -
Nonstop2h 20m
Deal found 8/10![Breeze Airways logo]()
$117
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:35 am -
Nonstop2h 10m
Fri 8/287:35 am -
Nonstop2h 20m
Deal found 8/11![Breeze Airways logo]()
$128
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:30 am -
Nonstop2h 09m
Mon 8/3110:59 am -
Nonstop2h 21m
Deal found 8/12![Allegiant Air logo]()
$137
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:35 am -
Nonstop2h 10m
Mon 9/77:35 am -
Nonstop2h 20m
Deal found 8/11![Breeze Airways logo]()
$133
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:20 am -
Nonstop2h 09m
Mon 9/1412:39 pm -
Nonstop2h 18m
Deal found 8/14![Allegiant Air logo]()
$83
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/2112:39 pm -
Nonstop2h 18m
Deal found 8/13![Allegiant Air logo]()
$102
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/2812:39 pm -
Nonstop2h 18m
Deal found 8/13![Allegiant Air logo]()
$145
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.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/288:18 pm -
2 stops37h 30m
Deal found 8/13![Multiple Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 9/199:30 am -
Nonstop2h 15m
Sat 9/2612:35 pm -
Nonstop2h 26m
Deal found 8/10![Allegiant Air logo]()
$157
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:43 am -
1 stop6h 35m
Mon 9/283:16 pm -
1 stop18h 32m
Deal found 8/14![Frontier logo]()
$162
One-way flights from Kentucky to MassachusettsSearch for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 15, 2026.
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.
Fri 9/117:20 am -
Nonstop2h 09m
Deal found 8/13![Allegiant Air logo]()
$43
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.
Fri 11/1312:20 pm -
Nonstop2h 09m
Deal found 8/12![Allegiant Air logo]()
$52
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:30 am -
Nonstop2h 12m
Deal found 8/11![Allegiant Air logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 11/612:20 pm -
Nonstop2h 09m
Deal found 8/10![Allegiant Air logo]()
$54
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:22 pm -
Nonstop2h 08m
Deal found 8/14![Allegiant Air logo]()
$57
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:30 am -
Nonstop2h 15m
Deal found 8/13![Allegiant Air logo]()
$60
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:35 am -
Nonstop2h 10m
Deal found 8/14![Breeze Airways logo]()
$64
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 11/17:30 am -
Nonstop2h 12m
Deal found 8/10![Allegiant Air logo]()
$67
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:00 am -
Nonstop2h 09m
Deal found 8/14![Allegiant Air logo]()
$67
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:30 am -
Nonstop2h 15m
Deal found 8/11![Allegiant Air logo]()
$68
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.
Fri 9/410:35 am -
Nonstop2h 10m
Deal found 8/13![Breeze Airways logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Wed 9/95:40 pm -
1 stop19h 38m
Deal found 8/10![Frontier logo]()
$76
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 August 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $83 (Kiwi.com) |
One-way from | $43 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $408 |
Good round-trip deal | $441 or less |
Good one-way deal | $277 or less |
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 15, 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
Cheapest round-trip
NashvilleHartford
BNA Nashville Intl - BDL Hartford Bradley Intl
BNABDL
Nashville Intl
Tue 10/20
3:05 pm-11:59 pm
2 stops7h 54m
Hartford Bradley Intl
Sat 10/24
9:44 am-2:20 pm
1 stop5h 36m
$202
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Tue 9/29
5:35 pm-9:17 pm
Nonstop2h 42m
Boston Logan Intl
Mon 10/5
7:50 pm-9:44 pm
Nonstop2h 54m
$219
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Sat 9/5
12:00 pm-3:50 pm
Nonstop2h 50m
Boston Logan Intl
Wed 9/9
6:55 pm-8:51 pm
Nonstop2h 56m
$219
NashvilleHartford
BNA Nashville Intl - BDL Hartford Bradley Intl
BNABDL
Nashville Intl
Wed 9/23
6:02 am-2:05 pm
2 stops7h 03m
Hartford Bradley Intl
Sun 9/27
6:00 am-9:31 am
1 stop4h 31m
$234
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Thu 9/17
6:33 pm-1:10 am
1 stop5h 37m
Boston Logan Intl
Sun 9/20
5:45 am-9:34 am
1 stop4h 49m
$239
Quickest round-trip
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Mon 10/26
8:20 pm-11:50 pm
Nonstop2h 30m
Boston Logan Intl
Fri 10/30
6:05 pm-7:50 pm
Nonstop2h 45m
$248
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Thu 10/22
5:10 pm-12:05 am
2 stops5h 55m
Boston Logan Intl
Tue 10/27
5:35 am-11:30 am
2 stops6h 55m
$251
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 11/10
3:10 pm-9:50 pm
1 stop6h 40m
Boston Logan Intl
Sat 11/14
7:25 am-12:55 pm
1 stop5h 30m
$251
CincinnatiAlbany
CVG Cincinnati Cinci./N. Kentucky - ALB Albany Intl
CVGALB
Cincinnati Cinci./N. Kentucky
Wed 9/16
6:28 pm-11:57 pm
1 stop5h 29m
Albany Intl
Mon 9/21
6:23 pm-12:23 am
1 stop6h 00m
$257
LouisvilleHartford
SDF Louisville Intl - BDL Hartford Bradley Intl
SDFBDL
Louisville Intl
Thu 9/17
5:15 am-10:34 am
1 stop5h 19m
Hartford Bradley Intl
Tue 9/22
12:12 pm-8:32 pm
1 stop8h 20m
$257
Showing 1-10 of 60 resultsSorted by cheapest first
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.
BNA-ALB
SDF-BDL
TYS-BOS
BNA-BDL
BNA-BOS
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
USKY-USMA
BNA-ALB
SDF-BDL
TYS-BOS
BNA-BDL
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 $357). Flying from Kentucky to Massachusetts in April is currently the most expensive (average of $495). 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 15, 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.
How much does it cost to fly round-trip from Kentucky to Massachusetts?
Airfare is below average for this route at the moment.
Kentucky to Massachusetts flights typically cost between $371 and $464 in November.The cheapest round-trip price found within the last 5 days was $251 on Southwest (Nov 10-Nov 14).
How far ahead should I book a flight from Kentucky to Massachusetts?
The price you pay for your flight from Kentucky to Massachusetts may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 15, 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.
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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.
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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.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Massachusetts by cabin class
Find flights from Kentucky to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Massachusetts flights
Browse other Kentucky and Massachusetts flight options. Last updated on August 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Kentucky after your stay in Massachusetts
Kentucky to Massachusetts flights
Consider these flights traveling from Kentucky to Massachusetts.
Top 4 airlines flying from Kentucky to Massachusetts
Discover the top 4 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$396 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$204 | Average$389 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$293 | Average$413 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$437 | FlexibilityNo cancel fee | On-time69% |