$172+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Oct 29 — Nov 51
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Massachusetts with Cheapflights
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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 September 29, 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 September 29, 2026.
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/46:30 am -
1 stop10h 10m
Sat 11/710:18 am -
1 stop9h 39m
Deal found 9/28![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/276:00 am -
1 stop8h 51m
Tue 11/38:16 am -
1 stop9h 27m
Deal found 9/29![American Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/24. 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 11/111:08 am -
1 stop4h 25m
Deal found 9/24![American Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/34:41 pm -
1 stop7h 07m
Deal found 9/28![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/24. 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 10/296:55 am -
1 stop4h 27m
Sun 11/15:39 am -
1 stop5h 12m
Deal found 9/24![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/295:30 am -
1 stop4h 48m
Sun 11/15:30 am -
2 stops7h 43m
Deal found 9/28![United Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/28. 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 12/35:00 am -
2 stops7h 27m
Thu 12/313:31 pm -
2 stops8h 28m
Deal found 9/28![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/1711:14 am -
1 stop8h 19m
Wed 10/2111:21 am -
1 stop5h 08m
Deal found 9/27![American Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 9/24. 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 11/73:25 pm -
1 stop6h 40m
Tue 11/102:25 pm -
1 stop6h 15m
Deal found 9/24![Southwest logo]()
$366
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Sat 11/711:08 am -
1 stop4h 35m
Tue 11/1012:39 pm -
1 stop8h 48m
Deal found 9/28![American Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 9/25. 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 11/47:20 am -
1 stop6h 20m
Mon 11/97:45 pm -
1 stop4h 40m
Deal found 9/25![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 9/28. 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 10/2710:40 am -
1 stop4h 15m
Thu 10/2912:55 pm -
1 stop9h 40m
Deal found 9/28![Southwest logo]()
$382
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 September 29, 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 September 29, 2026.
This Delta deal was found by Cheapflights users on 9/25. 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 10/305:53 pm -
1 stop6h 06m
Sun 11/19:00 am -
1 stop4h 53m
Deal found 9/25![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/24. 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
Mon 11/239:00 am -
2 stops8h 30m
Deal found 9/24![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 9/27. 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 11/95:40 am -
1 stop4h 00m
Mon 11/97:45 pm -
1 stop4h 40m
Deal found 9/27![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 9/28. 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 10/305:59 pm -
1 stop5h 15m
Tue 11/310:00 am -
1 stop4h 42m
Deal found 9/28![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/295:30 am -
1 stop4h 48m
Tue 11/312:00 pm -
2 stops8h 35m
Deal found 9/28![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 9/25. 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 10/283:34 pm -
1 stop5h 34m
Sat 10/316:50 am -
1 stop7h 59m
Deal found 9/25![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/25. 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 12/512:45 pm -
2 stops9h 15m
Mon 12/71:10 pm -
2 stops7h 25m
Deal found 9/25![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/27. 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 11/71:40 pm -
2 stops8h 25m
Tue 11/101:10 pm -
2 stops7h 30m
Deal found 9/27![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/27. 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 10/303:35 pm -
2 stops8h 00m
Tue 11/35:30 am -
1 stop7h 30m
Deal found 9/27![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 9/24. 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 11/411:05 am -
1 stop6h 19m
Sat 11/77:30 am -
2 stops10h 00m
Deal found 9/24![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 9/27. 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 10/310:55 am -
1 stop7h 05m
Wed 10/147:00 am -
1 stop7h 42m
Deal found 9/27![Delta logo]()
$406
This Southwest deal was found by Cheapflights users on 9/28. 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 12/114:40 pm -
2 stops7h 10m
Mon 12/141:10 pm -
2 stops7h 25m
Deal found 9/28![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 9/25. 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 9/25![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 9/24. 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 11/31:20 pm -
Nonstop2h 37m
Sat 11/712:00 pm -
Nonstop2h 40m
Deal found 9/24![Delta logo]()
$425
This United Airlines deal was found by Cheapflights users on 9/26. 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 10/135:15 pm -
1 stop5h 44m
Tue 10/209:30 am -
1 stop5h 10m
Deal found 9/26![United Airlines logo]()
$475
This Delta deal was found by Cheapflights users on 9/25. 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 10/36:00 pm -
1 stop5h 58m
Tue 10/137:00 am -
1 stop7h 42m
Deal found 9/25![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 9/25. 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 10/175:53 pm -
1 stop6h 06m
Sun 10/255:39 am -
1 stop4h 09m
Deal found 9/25![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/135:00 am -
1 stop5h 01m
Sat 10/177:01 am -
1 stop7h 31m
Deal found 9/28![United Airlines logo]()
$494
This Delta deal was found by Cheapflights users on 9/28. 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 10/301:20 pm -
Nonstop2h 37m
Tue 11/39:45 am -
Nonstop2h 42m
Deal found 9/28![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/22:25 pm -
1 stop17h 54m
Thu 11/59:12 am -
1 stop14h 53m
Deal found 9/23![United Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 9/27. 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 11/241:30 pm -
Nonstop2h 31m
Fri 11/279:05 am -
1 stop7h 49m
Deal found 9/27![Delta logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/165:15 pm -
1 stop5h 44m
Mon 10/199:51 am -
2 stops14h 24m
Deal found 9/24![United Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 9/28. 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 10/271:20 pm -
Nonstop2h 37m
Tue 11/39:45 am -
Nonstop2h 42m
Deal found 9/28![Delta logo]()
$456
This Delta deal was found by Cheapflights users on 9/25. 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 12/51:45 pm -
Nonstop2h 21m
Mon 12/79:55 am -
Nonstop2h 54m
Deal found 9/25![Delta logo]()
$464
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/95:00 am -
1 stop5h 01m
Tue 10/138:05 am -
1 stop6h 27m
Deal found 9/24![United Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 9/28. 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 10/299:53 am -
1 stop5h 01m
Tue 11/36:00 am -
1 stop5h 10m
Deal found 9/28![Delta logo]()
$464
This United Airlines deal was found by Cheapflights users on 9/25. 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 10/95:00 am -
1 stop5h 01m
Sun 10/116:00 am -
2 stops8h 32m
Deal found 9/25![United Airlines logo]()
$705
This United Airlines deal was found by Cheapflights users on 9/27. 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 10/115:00 am -
2 stops10h 59m
Wed 10/147:13 pm -
2 stops19h 19m
Deal found 9/27![United Airlines logo]()
$723
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated September 29, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated September 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/28. 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 10/71:20 pm -
Nonstop2h 37m
Tue 10/139:45 am -
Nonstop2h 42m
Deal found 9/28![Delta logo]()
$507
This Delta deal was found by Cheapflights users on 9/28. 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 10/75:59 pm -
1 stop5h 21m
Wed 10/149:05 am -
1 stop5h 36m
Deal found 9/28![Delta logo]()
$527
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/135:15 pm -
1 stop5h 44m
Sat 10/177:38 am -
2 stops7h 02m
Deal found 9/28![United Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/135:15 pm -
1 stop5h 44m
Tue 10/209:30 am -
1 stop5h 10m
Deal found 9/28![United Airlines logo]()
$475
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/135:00 am -
1 stop5h 01m
Sat 10/177:01 am -
1 stop7h 31m
Deal found 9/28![United Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/1711:14 am -
1 stop8h 19m
Wed 10/2111:21 am -
1 stop5h 08m
Deal found 9/27![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 9/24. 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 10/237:59 pm -
1 stop5h 21m
Sun 10/255:39 am -
1 stop4h 09m
Deal found 9/24![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/24. 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 11/111:08 am -
1 stop4h 25m
Deal found 9/24![American Airlines logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/34:41 pm -
1 stop7h 07m
Deal found 9/28![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/24. 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 10/296:55 am -
1 stop4h 27m
Sun 11/15:39 am -
1 stop5h 12m
Deal found 9/24![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/295:30 am -
1 stop4h 48m
Tue 11/312:00 pm -
2 stops8h 35m
Deal found 9/28![United Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/302:25 pm -
1 stop8h 04m
Wed 11/49:30 am -
1 stop5h 10m
Deal found 9/28![United Airlines logo]()
$450
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 September 29, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/258:42 pm -
1 stop15h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Allegiant Air logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/169:14 pm -
1 stop12h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Allegiant Air logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/308:10 pm -
1 stop13h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Allegiant Air logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/238:10 pm -
1 stop13h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Allegiant Air logo]()
$182
This Southwest deal was found by Cheapflights users on 9/24. 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 10/207:35 am -
2 stops8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 9/28. 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 10/273:55 pm -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Southwest logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/25. 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 10/229:09 pm -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/298:34 pm -
1 stop13h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Allegiant Air logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/299:09 pm -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/298:51 pm -
2 stops35h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Allegiant Air logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/309:18 pm -
2 stops37h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Allegiant Air logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/24. 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 10/229:13 pm -
3 stops37h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$240
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 September 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $313 (American Airlines) |
One-way from | $172 (Kiwi.com) |
Popular in | April |
Cheapest in | December |
Average price | $487 |
Good round-trip deal | $487 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 September 29, 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
Fri 10/16
9:14 pm-9:29 am
1 stop12h 15m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 10/28
3:55 pm-10:45 pm
1 stop6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 3/3
7:05 am-2:00 pm
1 stop6h 55m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 2/2
6:40 am-4:05 pm
2 stops9h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$194
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Mon 12/14
8:50 am-4:50 pm
2 stops8h 00m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$194
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 10/6
3:55 pm-10:45 pm
1 stop6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Tue 12/22
5:50 pm-1:18 am
1 stop7h 28m
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
Sun 10/18
7:59 pm-1:20 am
1 stop5h 21m
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
Tue 12/29
5:50 pm-1:18 am
1 stop7h 28m
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
Thu 12/24
5:49 pm-11:59 pm
1 stop6h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Showing 1-10 of 52 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.
LEX-BOS
OWB-BOS
PAH-BOS
SDF-BOS
SDF-ACK
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
LEX-BOS
OWB-BOS
PAH-BOS
SDF-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 $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 September 29, 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 $364 and $548 in November.The cheapest round-trip price found within the last 5 days was $313 on American Airlines (Nov 4-Nov 7).
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 September 29, 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.
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Boarding
8.1
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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 September 29, 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 September 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$411 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$411 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$275 | Average$415 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$437 | FlexibilityNo cancel fee | On-time69% |