$121+ Cheap flights from Kentucky to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Nov 13 — Nov 201
Round-trip
1 adult, Economy
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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 October 14, 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 October 14, 2026.
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Wed 12/95:55 am -
1 stop8h 56m
Mon 12/149:26 am -
1 stop8h 28m
Deal found 10/10![American Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 10/9. 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.
Mon 12/144:00 pm -
1 stop4h 29m
Fri 1/112:00 pm -
1 stop7h 00m
Deal found 10/9![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/9. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Tue 11/312:33 pm -
1 stop5h 51m
Deal found 10/9![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Sun 11/19:44 am -
1 stop5h 49m
Deal found 10/10![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/136:54 pm -
2 stops22h 13m
Sun 11/155:36 pm -
2 stops17h 20m
Deal found 10/9![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Sat 12/57:00 am -
2 stops7h 32m
Mon 12/73:42 pm -
2 stops8h 14m
Deal found 10/11![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/9. 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 10/295:58 pm -
1 stop6h 01m
Thu 11/59:00 am -
1 stop5h 42m
Deal found 10/9![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 am -
1 stop8h 12m
Mon 11/169:23 am -
1 stop8h 20m
Deal found 10/12![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/9. 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 10/297:10 am -
2 stops7h 22m
Tue 11/33:01 pm -
1 stop5h 34m
Deal found 10/9![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/13. 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 10/316:00 am -
1 stop5h 02m
Tue 11/38:00 am -
1 stop6h 42m
Deal found 10/13![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 10/13. 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 11/127:10 am -
2 stops7h 22m
Thu 11/191:29 pm -
1 stop5h 41m
Deal found 10/13![United Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 10/291:49 pm -
1 stop5h 25m
Mon 11/21:29 pm -
1 stop5h 41m
Deal found 10/14![United Airlines logo]()
$369
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 October 14, 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 October 14, 2026.
This Delta deal was found by Cheapflights users on 10/12. 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 11/135:59 pm -
1 stop5h 23m
Fri 11/208:00 am -
1 stop7h 11m
Deal found 10/12![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 11/1111:05 am -
2 stops7h 29m
Wed 11/186:36 pm -
1 stop5h 18m
Deal found 10/13![United Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/136:54 pm -
2 stops22h 13m
Sun 11/155:36 pm -
2 stops17h 20m
Deal found 10/9![American Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 10/11. 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.
Sat 12/195:40 am -
1 stop4h 00m
Tue 12/2210:25 pm -
1 stop11h 35m
Deal found 10/11![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 10/10. 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.
Fri 11/207:00 am -
1 stop4h 25m
Sun 11/225:30 am -
1 stop4h 23m
Deal found 10/10![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Thu 10/2911:05 am -
2 stops7h 52m
Thu 11/56:36 pm -
1 stop5h 18m
Deal found 10/10![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 11/55:53 pm -
1 stop6h 06m
Sun 11/85:39 am -
1 stop4h 09m
Deal found 10/12![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/9. 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 11/1112:55 pm -
2 stops9h 00m
Fri 11/1312:55 pm -
2 stops9h 20m
Deal found 10/9![Southwest logo]()
$450
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 10/3011:05 am -
2 stops7h 29m
Mon 11/26:36 pm -
1 stop5h 18m
Deal found 10/10![United Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 10/13. 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 12/236:56 pm -
1 stop6h 20m
Tue 12/295:15 pm -
Nonstop2h 55m
Deal found 10/13![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 12/42:40 pm -
1 stop6h 13m
Mon 12/79:30 am -
1 stop5h 35m
Deal found 10/10![United Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 10/13. 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 11/27:05 am -
2 stops7h 25m
Wed 11/41:10 pm -
2 stops7h 30m
Deal found 10/13![Southwest logo]()
$499
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Sat 10/318:45 am -
1 stop4h 47m
Wed 11/46:36 pm -
1 stop5h 29m
Deal found 10/10![United Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 10/13. 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 10/243:34 pm -
1 stop5h 34m
Mon 10/266:00 pm -
1 stop5h 03m
Deal found 10/13![Delta logo]()
$449
This Southwest deal was found by Cheapflights users on 10/13. 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 11/25:35 pm -
2 stops6h 15m
Thu 11/55:20 am -
1 stop6h 50m
Deal found 10/13![Southwest logo]()
$503
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Fri 11/205:25 am -
1 stop4h 53m
Sun 11/225:30 am -
2 stops7h 43m
Deal found 10/10![United Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 10/12. 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 11/137:35 am -
2 stops7h 44m
Sun 11/154:03 pm -
1 stop7h 00m
Deal found 10/12![Delta logo]()
$478
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Mon 12/148:45 am -
1 stop5h 09m
Fri 1/19:30 am -
2 stops11h 08m
Deal found 10/9![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 10/10. 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.
Fri 11/201:30 pm -
Nonstop2h 31m
Sun 11/229:55 am -
Nonstop2h 47m
Deal found 10/10![Delta logo]()
$483
This United Airlines deal was found by Cheapflights users on 10/10. 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.
Sat 10/318:45 am -
2 stops8h 54m
Sun 11/16:36 pm -
1 stop5h 29m
Deal found 10/10![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 10/13. 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 11/251:30 pm -
Nonstop2h 31m
Sun 11/2910:30 am -
Nonstop2h 50m
Deal found 10/13![Delta logo]()
$484
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/96:00 am -
1 stop7h 55m
Tue 1/1211:52 am -
1 stop5h 30m
Deal found 10/12![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 10/9. 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 10/248:45 am -
1 stop5h 10m
Wed 10/289:30 am -
1 stop5h 10m
Deal found 10/9![United Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 10/12. 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.
Sat 10/172:35 pm -
Nonstop2h 36m
Thu 10/229:45 am -
Nonstop2h 42m
Deal found 10/12![Delta logo]()
$553
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 12/97:10 am -
3 stops16h 49m
Mon 12/147:33 pm -
1 stop19h 18m
Deal found 10/13![United Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Mon 10/265:30 am -
1 stop6h 16m
Fri 10/308:25 pm -
1 stop18h 16m
Deal found 10/11![United Airlines logo]()
$622
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/165:30 am -
1 stop6h 16m
Thu 11/197:31 am -
1 stop7h 10m
Deal found 10/14![United Airlines logo]()
$642
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Tue 10/275:30 am -
2 stops9h 20m
Fri 10/3010:42 am -
1 stop27h 59m
Deal found 10/13![United Airlines logo]()
$652
This United Airlines deal was found by Cheapflights users on 10/13. 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.
Wed 10/285:30 am -
1 stop6h 16m
Sun 11/17:31 am -
1 stop7h 10m
Deal found 10/13![United Airlines logo]()
$709
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Sun 10/255:30 am -
1 stop27h 48m
Thu 10/2911:55 am -
1 stop26h 46m
Deal found 10/9![United Airlines logo]()
$728
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated October 14, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/9. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Tue 11/312:33 pm -
1 stop5h 51m
Deal found 10/9![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Sun 11/19:44 am -
1 stop5h 49m
Deal found 10/10![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 10/9. 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 10/295:58 pm -
1 stop6h 01m
Thu 11/59:00 am -
1 stop5h 42m
Deal found 10/9![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/9. 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 10/297:10 am -
2 stops7h 22m
Tue 11/33:01 pm -
1 stop5h 34m
Deal found 10/9![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 10/291:49 pm -
1 stop5h 25m
Mon 11/21:29 pm -
1 stop5h 41m
Deal found 10/14![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 10/296:00 am -
1 stop7h 44m
Sun 11/15:39 am -
1 stop4h 01m
Deal found 10/12![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 10/13. 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 10/316:00 am -
1 stop5h 02m
Tue 11/38:00 am -
1 stop6h 42m
Deal found 10/13![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 10/10. 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.
Wed 11/44:04 pm -
1 stop7h 09m
Sat 11/710:20 am -
1 stop8h 04m
Deal found 10/10![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:30 am -
1 stop8h 12m
Mon 11/169:23 am -
1 stop8h 20m
Deal found 10/12![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/13. 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 11/127:10 am -
2 stops7h 22m
Thu 11/191:29 pm -
1 stop5h 41m
Deal found 10/13![United Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/136:54 pm -
2 stops22h 13m
Sun 11/155:36 pm -
2 stops17h 20m
Deal found 10/9![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:02 am -
1 stop8h 46m
Tue 12/19:22 am -
1 stop8h 28m
Deal found 10/11![American Airlines logo]()
$313
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 October 14, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
Sun 1/106:48 pm -
1 stop16h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Allegiant Air logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 10/10. 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.
Thu 1/76:48 pm -
1 stop16h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Allegiant Air logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 1/88:41 pm -
1 stop15h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Allegiant Air logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 11/138:54 pm -
1 stop12h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Thu 11/59:09 pm -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 10/10. 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.
Thu 1/79:04 pm -
2 stops38h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sun 1/109:39 pm -
1 stop11h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 10/10. 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.
Thu 11/128:02 pm -
2 stops36h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Allegiant Air logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 10/10. 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 11/1310:46 am -
2 stops21h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Allegiant Air logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 10/10. 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.
Thu 1/149:04 pm -
2 stops38h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 10/11. 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.
Sun 11/88:48 am -
2 stops24h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Allegiant Air logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 1/153:41 pm -
1 stop17h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Multiple Airlines logo]()
$218
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 October 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (American Airlines) |
One-way from | $121 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $433 |
Good round-trip deal | $483 or less |
Good one-way deal | $348 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 7,457,451 searches. Data last updated October 14, 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
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 1/6
3:35 pm-9:40 pm
1 stop6h 05m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Sun 12/13
3:42 pm-10:13 am
1 stop18h 31m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$228
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Sun 1/10
8:30 am-5:55 pm
2 stops9h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Sun 12/13
4:40 pm-11:50 pm
2 stops7h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$257
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 1/12
10:43 am-11:39 pm
2 stops12h 56m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$262
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 10/21
2:05 pm-6:35 pm
1 stop4h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Sat 10/24
9:25 am-3:40 pm
1 stop6h 15m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 10/20
7:35 am-4:05 pm
2 stops8h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Mon 4/12
4:15 pm-11:30 pm
1 stop7h 15m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Sat 11/14
6:00 am-1:42 pm
1 stop7h 42m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Showing 1-10 of 51 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.
SDF-BOS
LEX-BOS
LEX-ORH
OWB-BOS
PAH-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
SDF-BOS
LEX-BOS
LEX-ORH
OWB-BOS
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 $354). 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 October 14, 2026.
It’s optimal to fly from Kentucky to Massachusetts at noon. By choosing this option you can save up to 77% on the cost of your flight, compared to a flight in the evening.
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 $369 and $545 in December.The cheapest round-trip price found within the last 5 days was $313 on American Airlines (Dec 9-Dec 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 74 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 October 14, 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.
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Overall
7.9
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 October 14, 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 7,457,451 searches. Data last updated October 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$407 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$275 | Average$414 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$345 | Average$438 | FlexibilityNo cancel fee | On-time69% |