$159+ Cheap flights from Kentucky to Boston (BOS)
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 18 — Nov 251
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Boston with Cheapflights
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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 BostonExplore the most affordable flight options available from Kentucky to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
Explore the most affordable flight options available from Kentucky to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 19, 2026.
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/17:20 am -
1 stop6h 20m
Tue 12/15:35 pm -
1 stop4h 40m
Deal found 10/19![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 10/18. 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 12/235:35 pm -
1 stop5h 20m
Wed 12/3010:25 pm -
1 stop12h 05m
Deal found 10/18![Southwest logo]()
$293
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop10h 10m
Wed 11/1812:39 pm -
1 stop8h 48m
Deal found 10/14![American Airlines logo]()
$313
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:15 pm -
1 stop5h 25m
Mon 11/3010:25 pm -
1 stop12h 05m
Deal found 10/19![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/214:15 pm -
2 stops7h 40m
Tue 12/295:15 am -
1 stop10h 20m
Deal found 10/19![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 10/18. 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 11/207:55 pm -
1 stop5h 13m
Sun 11/225:30 am -
1 stop4h 23m
Deal found 10/18![Delta logo]()
$339
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.
Fri 11/65:25 am -
1 stop4h 53m
Mon 11/912:00 pm -
2 stops8h 35m
Deal found 10/14![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 10/18. 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 11/163:50 pm -
1 stop6h 25m
Mon 11/235:20 am -
1 stop6h 50m
Deal found 10/18![Southwest logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/18. 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 12/1411:10 am -
1 stop7h 43m
Fri 1/13:07 pm -
1 stop8h 39m
Deal found 10/18![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/16. 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 12/2511:17 am -
2 stops8h 54m
Tue 12/295:29 pm -
1 stop6h 17m
Deal found 10/16![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/17. 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 11/55:25 am -
2 stops7h 01m
Sun 11/86:36 pm -
1 stop5h 18m
Deal found 10/17![United Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:12 pm -
2 stops16h 59m
Thu 12/1010:29 am -
1 stop25h 19m
Deal found 10/15![Multiple Airlines logo]()
$362
Best flights from Kentucky to BostonDiscover carefully curated flight deals from Kentucky to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
Discover carefully curated flight deals from Kentucky to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 19, 2026.
This Delta deal was found by Cheapflights users on 10/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:53 pm -
1 stop6h 06m
Tue 11/106:45 am -
1 stop5h 04m
Deal found 10/15![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/18. 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 stops8h 01m
Tue 11/36:36 pm -
1 stop5h 18m
Deal found 10/18![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 10/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:10 pm -
1 stop6h 45m
Mon 11/95:10 pm -
1 stop7h 15m
Deal found 10/15![Southwest logo]()
$425
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:55 pm -
1 stop5h 21m
Sat 12/261:04 pm -
1 stop4h 07m
Deal found 10/14![Delta logo]()
$359
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/198:50 am -
2 stops8h 20m
Sun 11/225:10 am -
2 stops9h 55m
Deal found 10/14![Southwest logo]()
$427
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:32 pm -
1 stop6h 27m
Tue 12/295:00 pm -
1 stop5h 26m
Deal found 10/14![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/17. 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 10/17![United Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 10/16. 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 stop6h 34m
Tue 11/39:05 am -
1 stop5h 44m
Deal found 10/16![Delta logo]()
$399
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 12/248:30 am -
2 stops9h 57m
Tue 12/295:45 am -
1 stop7h 27m
Deal found 10/14![United Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:40 pm -
2 stops8h 25m
Mon 11/93:30 pm -
1 stop6h 45m
Deal found 10/19![Southwest logo]()
$457
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:55 pm -
1 stop5h 21m
Tue 12/295:00 pm -
1 stop5h 26m
Deal found 10/14![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/17. 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 10/17![United Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:05 am -
2 stops7h 25m
Fri 11/207:45 pm -
1 stop4h 40m
Deal found 10/18![Southwest logo]()
$481
This United Airlines deal was found by Cheapflights users on 10/16. 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 10/16![United Airlines logo]()
$460
This Southwest deal was found by Cheapflights users on 10/17. 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 11/165:40 am -
1 stop6h 40m
Tue 11/1712:50 pm -
1 stop7h 45m
Deal found 10/17![Southwest logo]()
$484
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/135:00 am -
1 stop4h 42m
Fri 1/226:00 am -
1 stop8h 28m
Deal found 10/19![United Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 10/17. 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 11/162:05 pm -
2 stops7h 40m
Wed 11/181:10 pm -
2 stops7h 30m
Deal found 10/17![Southwest logo]()
$494
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Fri 11/278:45 am -
2 stops12h 14m
Fri 1/84:54 pm -
1 stop7h 02m
Deal found 10/15![United Airlines logo]()
$470
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:35 pm -
Nonstop2h 36m
Wed 10/289:45 am -
Nonstop2h 42m
Deal found 10/14![Delta logo]()
$527
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:35 pm -
Nonstop2h 36m
Tue 10/279:45 am -
Nonstop2h 42m
Deal found 10/14![Delta logo]()
$527
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:25 pm -
1 stop8h 10m
Sat 11/74:56 pm -
1 stop7h 09m
Deal found 10/19![United Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 10/16. 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 11/411:50 am -
1 stop4h 40m
Sat 11/72:15 pm -
1 stop4h 55m
Deal found 10/16![Delta logo]()
$547
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Fri 10/305:30 am -
1 stop7h 29m
Tue 11/39:12 am -
1 stop5h 29m
Deal found 10/15![United Airlines logo]()
$514
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:30 am -
1 stop6h 16m
Sat 11/77:31 am -
1 stop7h 10m
Deal found 10/19![United Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:49 am -
1 stop5h 03m
Sun 11/295:30 am -
1 stop4h 39m
Deal found 10/19![Delta logo]()
$583
This United Airlines deal was found by Cheapflights users on 10/17. 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 11/276:00 am -
2 stops6h 26m
Fri 11/272:40 pm -
1 stop4h 50m
Deal found 10/17![United Airlines logo]()
$523
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 11/122:11 pm -
1 stop9h 48m
Sun 11/156:05 pm -
2 stops16h 29m
Deal found 10/14![United Airlines logo]()
$525
Last-minute flights from Kentucky to BostonDiscover last-minute flight deals from Kentucky to Boston. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Boston. Data last updated October 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Thu 11/53:21 pm -
1 stop8h 27m
Deal found 10/15![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 10/2911:05 am -
1 stop5h 06m
Tue 11/39:12 am -
1 stop8h 18m
Deal found 10/15![United Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/16. 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 10/16![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/17. 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 11/55:25 am -
2 stops7h 01m
Sun 11/86:36 pm -
1 stop5h 18m
Deal found 10/17![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.
Fri 11/65:25 am -
1 stop4h 53m
Mon 11/912:00 pm -
2 stops8h 35m
Deal found 10/14![United Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/68:54 pm -
1 stop12h 35m
Tue 11/1012:15 pm -
2 stops27h 11m
Deal found 10/18![Multiple Airlines logo]()
$372
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop10h 10m
Wed 11/1812:39 pm -
1 stop8h 48m
Deal found 10/14![American Airlines logo]()
$313
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop6h 32m
Mon 11/162:55 pm -
1 stop6h 33m
Deal found 10/14![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 10/18. 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 11/163:50 pm -
1 stop6h 25m
Mon 11/235:20 am -
1 stop6h 50m
Deal found 10/18![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:25 am -
2 stops7h 01m
Sun 11/227:31 am -
1 stop5h 42m
Deal found 10/19![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 10/18. 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 11/207:55 pm -
1 stop5h 13m
Sun 11/225:30 am -
1 stop4h 23m
Deal found 10/18![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:15 pm -
1 stop5h 25m
Mon 11/3010:25 pm -
1 stop12h 05m
Deal found 10/19![Southwest logo]()
$316
One-way flights from Kentucky to BostonSearch for one-way flight options from Kentucky to Boston. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
Search for one-way flight options from Kentucky to Boston. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 10/18![Allegiant Air logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/166:53 pm -
3 stops40h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Multiple Airlines logo]()
$167
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:40 pm -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/68:54 pm -
1 stop12h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Allegiant Air logo]()
$169
This Southwest deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:50 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 12/2410:08 am -
1 stop24h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Allegiant Air logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:42 pm -
1 stop16h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Allegiant Air logo]()
$189
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/224:15 pm -
2 stops7h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Southwest logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 1/109:09 pm -
3 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 10/17![Allegiant Air logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 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 10/15![Allegiant Air logo]()
$248
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.
Mon 11/239:38 am -
1 stop24h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$249
Find flight deals from Kentucky to Boston
Keep the following information in mind while searching for Kentucky to Boston flight deals. Data was last updated October 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Southwest) |
One-way from | $159 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $451 |
Good round-trip deal | $507 or less |
Good one-way deal | $388 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Boston 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 19, 2026.
Use the filters below to find and compare flights from Kentucky to Boston 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 11/13
4:40 pm-10:05 pm
1 stop5h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$168
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Mon 11/16
3:50 pm-10:15 pm
1 stop6h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$178
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 12/22
7:15 pm-12:35 am
1 stop5h 20m
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
Sat 11/7
3:25 pm-10:05 pm
1 stop6h 40m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 12/23
7:36 pm-11:43 am
1 stop16h 07m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Fri 12/4
3:50 pm-10:15 pm
1 stop6h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Fri 10/30
9:18 pm-10:42 am
2 stops37h 24m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$222
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Fri 11/13
10:46 am-8:19 am
2 stops21h 33m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$248
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Mon 11/23
9:38 am-10:11 am
1 stop24h 33m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$249
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Sun 11/22
3:29 pm-8:30 am
2 stops41h 01m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$253
Showing 1-10 of 48 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Kentucky with our price prediction graph.
SDF-BOS
LEX-BOS
PAH-BOS
OWB-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 Boston
USKY-BOS
SDF-BOS
LEX-BOS
PAH-BOS
OWB-BOS
What is the cheapest month to book a flight from Kentucky to Boston?
Currently, January is the cheapest month in which you can book a flight from Kentucky to Boston (average of $354). Flying from Kentucky to Boston 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 BOS?
Find hourly flight availability from Kentucky to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 19, 2026.
It’s typically best to fly out from Kentucky to Boston in the morning. Doing so could potentially save you 70% on the flight price compared to flying in the evening, which is usually more expensive.
Weekly flight availability from Kentucky to Boston
Explore weekly flight availability from Kentucky to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 19, 2026.
The most flights from USKY to BOS are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Kentucky to Boston?
Airfare is below average for this route at the moment.
Kentucky to Boston flights typically cost between $395 and $576 in December.The cheapest round-trip price found within the last 5 days was $287 on Southwest (Dec 1-Dec 1).
How far ahead should I book a flight from Kentucky to Boston?
Booking 74 days in advance of your planned departure date is, on average, the best time to get cheap flights from Kentucky to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Boston flight routes
Complete your trip
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Alternative routes for Kentucky to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 19, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Boston by cabin class
Find flights from Kentucky to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Boston flights
Browse other Kentucky and Boston flight options. Last updated on October 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Kentucky to Boston flights
Consider these flights traveling from Kentucky to Boston.
Top 4 airlines flying from Kentucky to Boston
Discover the top 4 airlines that operate flights from Kentucky to Boston. 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$406 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$275 | Average$415 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$345 | Average$438 | FlexibilityNo cancel fee | On-time69% |