$155+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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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 September 22, 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 September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 12/155:40 am -
1 stop4h 55m
Tue 12/1512:50 pm -
1 stop7h 40m
Deal found 9/17![Southwest logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Wed 11/46:30 am -
1 stop10h 10m
Sat 11/710:18 am -
1 stop9h 39m
Deal found 9/18![American Airlines logo]()
$313
This American Airlines deal was found by Cheapflights users on 9/19. 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 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 11/19:00 am -
Nonstop2h 30m
Deal found 9/19![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 11/105:40 am -
1 stop4h 55m
Fri 11/135:20 am -
1 stop6h 50m
Deal found 9/17![Southwest logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Mon 11/93:21 pm -
1 stop8h 27m
Deal found 9/18![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 11/135:30 am -
1 stop7h 29m
Mon 11/167:31 am -
1 stop7h 10m
Deal found 9/18![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 9/22![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Thu 10/295:30 am -
2 stops6h 56m
Tue 11/36:36 pm -
1 stop5h 18m
Deal found 9/19![United Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/65:53 pm -
1 stop17h 18m
Sun 12/1310:31 am -
1 stop25h 17m
Deal found 9/18![Allegiant Air logo]()
$350
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/105:53 pm -
1 stop6h 06m
Tue 10/136:50 am -
1 stop5h 08m
Deal found 9/22![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/175:35 am -
1 stop4h 25m
Sat 10/249:40 am -
1 stop8h 50m
Deal found 9/17![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/145:45 am -
1 stop4h 10m
Wed 10/285:35 am -
1 stop4h 25m
Deal found 9/19![Southwest logo]()
$357
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 September 22, 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 September 22, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/193:35 pm -
1 stop6h 30m
Sat 10/249:40 am -
1 stop8h 50m
Deal found 9/17![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 11/135:30 am -
1 stop7h 29m
Mon 11/167:31 am -
1 stop7h 10m
Deal found 9/18![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 2/278:20 am -
2 stops12h 21m
Thu 3/45:45 am -
1 stop5h 51m
Deal found 9/20![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/107:20 am -
1 stop6h 20m
Thu 11/123:30 pm -
1 stop6h 45m
Deal found 9/21![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/2812:50 pm -
2 stops8h 30m
Sat 10/3110:35 am -
1 stop4h 50m
Deal found 9/19![Southwest logo]()
$362
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/265:30 am -
1 stop4h 48m
Mon 11/26:00 am -
3 stops14h 35m
Deal found 9/17![United Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/253:14 pm -
1 stop4h 35m
Sat 11/289:55 am -
Nonstop2h 47m
Deal found 9/20![Delta logo]()
$435
This United Airlines deal was found by Cheapflights users on 9/17. 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 1/88:45 am -
1 stop4h 43m
Sun 1/109:30 am -
1 stop5h 10m
Deal found 9/17![United Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 9/19. 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 12/72:05 pm -
1 stop7h 35m
Wed 12/305:00 pm -
2 stops6h 05m
Deal found 9/19![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 9/18. 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.
Wed 10/143:34 pm -
1 stop5h 34m
Sun 10/185:39 am -
1 stop4h 09m
Deal found 9/18![Delta logo]()
$449
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Sat 1/911:00 am -
1 stop6h 49m
Tue 1/126:00 am -
1 stop7h 10m
Deal found 9/19![United Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/247:05 am -
2 stops8h 15m
Mon 10/265:50 am -
1 stop9h 10m
Deal found 9/21![Southwest logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/49:00 am -
2 stops9h 34m
Sat 11/71:29 pm -
1 stop7h 06m
Deal found 9/22![United Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Fri 12/48:45 am -
1 stop4h 47m
Mon 12/79:30 am -
1 stop5h 35m
Deal found 9/19![United Airlines logo]()
$450
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/144:00 pm -
2 stops6h 45m
Sun 10/255:35 am -
1 stop4h 20m
Deal found 9/19![Southwest logo]()
$468
This United Airlines deal was found by Cheapflights users on 9/19. 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 10/135:15 pm -
1 stop5h 44m
Tue 10/206:00 am -
2 stops8h 40m
Deal found 9/19![United Airlines logo]()
$460
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/55:40 am -
1 stop4h 00m
Sun 11/87:45 pm -
1 stop4h 40m
Deal found 9/21![Southwest logo]()
$473
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:15 pm -
2 stops5h 55m
Sun 11/15:20 am -
1 stop6h 50m
Deal found 9/21![Southwest logo]()
$478
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/197:10 am -
1 stop5h 36m
Sun 11/226:00 am -
1 stop7h 13m
Deal found 9/20![United Airlines logo]()
$484
This Southwest deal was found by Cheapflights users on 9/17. 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.
Tue 10/63:55 pm -
1 stop6h 50m
Sat 10/105:35 am -
2 stops9h 20m
Deal found 9/17![Southwest logo]()
$483
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 1/15:50 pm -
1 stop7h 28m
Sat 1/99:45 am -
2 stops10h 47m
Deal found 9/20![United Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/210:11 am -
1 stop6h 10m
Tue 10/66:43 pm -
1 stop5h 12m
Deal found 9/17![United Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Sat 10/36:00 am -
2 stops8h 55m
Wed 10/75:45 am -
2 stops7h 36m
Deal found 9/18![United Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Wed 10/710:11 am -
1 stop6h 10m
Sat 10/106:43 pm -
1 stop5h 12m
Deal found 9/18![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/65:00 am -
2 stops10h 46m
Sat 10/107:55 am -
1 stop6h 37m
Deal found 9/21![United Airlines logo]()
$522
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/45:00 am -
1 stop27h 33m
Wed 10/76:00 am -
1 stop8h 32m
Deal found 9/20![United Airlines logo]()
$677
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Sat 10/32:23 pm -
1 stop21h 01m
Wed 10/75:45 am -
2 stops8h 47m
Deal found 9/18![United Airlines logo]()
$738
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Sun 10/45:00 am -
2 stops8h 55m
Thu 10/86:00 am -
1 stop8h 32m
Deal found 9/19![United Airlines logo]()
$761
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 stop6h 48m
Sun 10/117:01 am -
1 stop7h 31m
Deal found 9/20![United Airlines logo]()
$789
Last-minute flights from Kentucky to BostonDiscover last-minute flight deals from Kentucky to Boston. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Boston. Data last updated September 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/105:53 pm -
1 stop6h 06m
Tue 10/136:50 am -
1 stop5h 08m
Deal found 9/22![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop8h 51m
Tue 10/209:26 am -
1 stop7h 57m
Deal found 9/22![American Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 9/18. 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.
Tue 10/1310:28 am -
1 stop5h 47m
Sun 10/255:39 am -
1 stop4h 09m
Deal found 9/18![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 9/19. 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.
Wed 10/145:45 am -
1 stop4h 10m
Wed 10/285:35 am -
1 stop4h 25m
Deal found 9/19![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/169:14 pm -
1 stop12h 15m
Mon 10/2611:47 am -
2 stops46h 24m
Deal found 9/17![Multiple Airlines logo]()
$361
This Southwest deal was found by Cheapflights users on 9/17. 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.
Sat 10/175:35 am -
1 stop4h 25m
Sat 10/249:40 am -
1 stop8h 50m
Deal found 9/17![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:35 pm -
1 stop6h 30m
Wed 10/216:45 am -
2 stops8h 35m
Deal found 9/20![Southwest logo]()
$362
This American Airlines deal was found by Cheapflights users on 9/19. 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 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 11/19:00 am -
Nonstop2h 30m
Deal found 9/19![American Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Thu 10/291:22 pm -
Nonstop2h 31m
Mon 11/93:21 pm -
1 stop8h 27m
Deal found 9/18![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 9/22![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Thu 10/295:30 am -
2 stops6h 56m
Tue 11/36:36 pm -
1 stop5h 18m
Deal found 9/19![United Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/3011:05 am -
2 stops7h 29m
Tue 11/37:31 am -
1 stop5h 42m
Deal found 9/18![United Airlines logo]()
$362
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 September 22, 2026.
Search for one-way flight options from Kentucky to Boston. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/169:14 pm -
1 stop12h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Allegiant Air logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 3/176:08 pm -
1 stop17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Allegiant Air logo]()
$173
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/2010:40 am -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/189:02 pm -
1 stop15h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Allegiant Air logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Sat 10/1712:12 pm -
1 stop23h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Allegiant Air logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 9/20![Multiple Airlines logo]()
$190
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:00 pm -
2 stops6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/188:59 pm -
3 stops38h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/159:11 pm -
3 stops37h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Tue 12/1511:24 am -
2 stops46h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Allegiant Air logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/1811:04 am -
1 stop24h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Allegiant Air logo]()
$246
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/185:15 pm -
1 stop5h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$314
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $275 (Southwest) |
One-way from | $155 (Kiwi.com) |
Popular in | April |
Cheapest in | December |
Average price | $487 |
Good round-trip deal | $453 or less |
Good one-way deal | $308 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 September 22, 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
Tue 10/20
2:05 pm-6:35 pm
1 stop4h 30m
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
Tue 3/16
6:00 pm-11:50 pm
1 stop5h 50m
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
Sat 3/20
5:45 am-12:35 pm
1 stop6h 50m
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
Mon 10/19
3:35 pm-11:55 pm
2 stops8h 20m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Tue 9/29
5:00 pm-9:30 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 10/3
7:05 am-3:20 pm
2 stops8h 15m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$269
Quickest round-trip
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Sun 10/11
5:50 am-9:55 am
1 stop4h 05m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$276
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Wed 11/18
5:25 am-12:46 pm
1 stop7h 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
Thu 10/15
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
Wed 12/23
10:45 am-5:36 pm
1 stop6h 51m
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 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
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 Boston
USKY-BOS
SDF-BOS
LEX-BOS
OWB-BOS
PAH-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 $357). 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 September 22, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Boston as you normally would.
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 $387 and $568 in December.The cheapest round-trip price found within the last 5 days was $275 on Southwest (Dec 15-Dec 15).
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
Revere
Warwick
Pawtucket
Peabody
Auburn
Londonderry
York Beach
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
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 September 22, 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 September 22, 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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$410 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$416 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$294 | Average$437 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$320 | Average$430 | FlexibilityNo cancel fee | On-time63% |