$166+ Cheap flights from Boston (BOS) to Kentucky
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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Dec 9 — Dec 161
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Kentucky with Cheapflights
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Cheapest flights from Boston to KentuckyExplore the most affordable flight options available from Boston to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 9, 2026.
Explore the most affordable flight options available from Boston to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 9, 2026.
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/115:56 pm -
1 stop5h 55m
Sun 12/1311:10 am -
1 stop7h 43m
Deal found 11/8![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/183:00 pm -
1 stop5h 40m
Fri 12/256:00 am -
1 stop8h 03m
Deal found 11/5![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:35 am -
1 stop5h 40m
Sun 12/65:00 am -
2 stops7h 27m
Deal found 11/6![United Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:45 am -
2 stops7h 17m
Fri 12/1110:50 am -
1 stop7h 05m
Deal found 11/6![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:16 am -
1 stop6h 53m
Fri 11/274:09 pm -
1 stop5h 26m
Deal found 11/5![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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.
Sun 11/225:30 am -
1 stop4h 23m
Wed 12/25:59 pm -
1 stop5h 59m
Deal found 11/5![Delta logo]()
$364
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:27 am -
1 stop4h 33m
Wed 12/166:00 am -
1 stop7h 42m
Deal found 11/9![Delta logo]()
$365
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:02 am -
1 stop7h 37m
Thu 11/265:15 am -
2 stops10h 51m
Deal found 11/5![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/218:50 am -
1 stop14h 33m
Fri 12/256:00 am -
1 stop8h 03m
Deal found 11/5![Delta logo]()
$372
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:02 am -
1 stop7h 37m
Fri 11/274:09 pm -
1 stop5h 26m
Deal found 11/5![American Airlines logo]()
$374
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2011:08 am -
1 stop4h 31m
Tue 11/245:15 am -
1 stop5h 07m
Deal found 11/5![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/235:30 am -
2 stops7h 43m
Fri 11/271:49 pm -
1 stop5h 21m
Deal found 11/8![United Airlines logo]()
$384
Best flights from Boston to KentuckyDiscover carefully curated flight deals from Boston to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 9, 2026.
Discover carefully curated flight deals from Boston to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 9, 2026.
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/216:38 pm -
1 stop5h 21m
Mon 12/285:50 pm -
1 stop7h 28m
Deal found 11/8![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 4/203:00 pm -
1 stop7h 15m
Wed 4/285:55 pm -
1 stop5h 31m
Deal found 11/7![Delta logo]()
$414
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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.
Sun 2/711:35 am -
2 stops10h 55m
Wed 2/103:55 pm -
1 stop5h 50m
Deal found 11/8![Southwest logo]()
$460
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:35 am -
1 stop5h 40m
Sun 12/65:00 am -
2 stops7h 27m
Deal found 11/6![United Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:45 am -
2 stops7h 17m
Fri 12/1110:50 am -
1 stop7h 05m
Deal found 11/6![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/45:45 am -
2 stops7h 17m
Sun 12/65:00 am -
1 stop5h 31m
Deal found 11/5![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 4/206:00 am -
1 stop5h 03m
Tue 4/275:00 pm -
1 stop4h 27m
Deal found 11/7![Delta logo]()
$455
This KAYAK deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:20 pm -
1 stop8h 55m
Thu 12/107:20 am -
3 stops11h 25m
Deal found 11/4![Southwest logo]()
$468
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/231:29 pm -
1 stop7h 06m
Fri 11/271:49 pm -
1 stop5h 21m
Deal found 11/8![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/29:05 am -
1 stop5h 24m
Sun 12/67:41 am -
1 stop4h 18m
Deal found 11/7![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 2/198:00 am -
2 stops8h 35m
Sun 2/215:15 pm -
1 stop4h 05m
Deal found 11/7![Southwest logo]()
$485
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 3/179:30 am -
Nonstop2h 48m
Sun 3/216:05 am -
1 stop6h 16m
Deal found 11/6![Delta logo]()
$484
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:38 pm -
1 stop5h 21m
Fri 1/18:30 am -
2 stops9h 57m
Deal found 11/6![United Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 3/195:15 pm -
1 stop7h 15m
Tue 3/234:30 pm -
1 stop6h 35m
Deal found 11/4![Southwest logo]()
$494
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 4/219:30 am -
Nonstop2h 48m
Sun 4/256:05 am -
1 stop6h 16m
Deal found 11/6![Delta logo]()
$484
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/256:36 pm -
1 stop5h 29m
Fri 11/278:45 am -
2 stops7h 42m
Deal found 11/5![United Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 3/1012:55 pm -
1 stop4h 45m
Sun 3/146:05 am -
1 stop7h 16m
Deal found 11/8![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 4/164:00 pm -
1 stop5h 01m
Tue 4/208:20 am -
1 stop5h 29m
Deal found 11/6![Delta logo]()
$494
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 1/157:15 am -
2 stops10h 07m
Sun 1/176:00 am -
1 stop6h 42m
Deal found 11/5![United Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/295:45 am -
1 stop7h 27m
Thu 1/76:00 am -
2 stops12h 20m
Deal found 11/7![United Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/266:00 am -
2 stops11h 30m
Fri 11/277:10 am -
2 stops10h 17m
Deal found 11/5![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:45 pm -
1 stop7h 09m
Tue 12/82:40 pm -
1 stop6h 13m
Deal found 11/5![United Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/86:00 am -
1 stop8h 17m
Sat 12/125:00 am -
1 stop7h 54m
Deal found 11/6![United Airlines logo]()
$474
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/225:45 am -
1 stop8h 58m
Mon 12/285:00 am -
2 stops9h 50m
Deal found 11/7![United Airlines logo]()
$730
Last-minute flights from Boston to KentuckyDiscover last-minute flight deals from Boston to Kentucky. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Kentucky. Data last updated November 9, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2011:08 am -
1 stop4h 31m
Tue 11/245:15 am -
1 stop5h 07m
Deal found 11/5![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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.
Sun 11/225:30 am -
1 stop4h 23m
Wed 12/25:59 pm -
1 stop5h 59m
Deal found 11/5![Delta logo]()
$364
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:02 am -
1 stop7h 37m
Thu 11/265:15 am -
2 stops10h 51m
Deal found 11/5![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:02 am -
1 stop7h 37m
Fri 11/274:09 pm -
1 stop5h 26m
Deal found 11/5![American Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/235:30 am -
2 stops7h 43m
Fri 11/271:49 pm -
1 stop5h 21m
Deal found 11/8![United Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2610:16 am -
1 stop6h 53m
Fri 11/274:09 pm -
1 stop5h 26m
Deal found 11/5![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:45 am -
2 stops7h 17m
Fri 12/1110:50 am -
1 stop7h 05m
Deal found 11/6![United Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:35 am -
1 stop5h 40m
Sun 12/65:00 am -
2 stops7h 27m
Deal found 11/6![United Airlines logo]()
$350
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/95:27 am -
1 stop4h 33m
Wed 12/166:00 am -
1 stop7h 42m
Deal found 11/9![Delta logo]()
$365
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/115:56 pm -
1 stop5h 55m
Sun 12/1311:10 am -
1 stop7h 43m
Deal found 11/8![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/184:00 pm -
1 stop4h 40m
Thu 12/2410:30 am -
1 stop7h 48m
Deal found 11/5![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/218:50 am -
1 stop14h 33m
Thu 12/2410:30 am -
1 stop7h 48m
Deal found 11/5![Delta logo]()
$372
One-way flights from Boston to KentuckySearch for one-way flight options from Boston to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
Search for one-way flight options from Boston to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 4/2610:16 am -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Allegiant Air logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/1310:31 am -
1 stop25h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Allegiant Air logo]()
$168
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/307:00 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$189
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 11/215:26 pm -
1 stop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![American Airlines logo]()
$190
This Southwest deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/175:30 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Southwest logo]()
$203
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/73:30 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/113:30 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Southwest logo]()
$214
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:30 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Sun 12/137:25 am -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Southwest logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 11/219:25 am -
2 stops29h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/2410:29 am -
1 stop7h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Allegiant Air logo]()
$268
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/15:20 am -
1 stop6h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$289
Find flight deals from Boston to Kentucky
Keep the following information in mind while searching for Boston to Kentucky flight deals. Data was last updated November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $345 (American Airlines) |
One-way from | $166 (Kiwi.com) |
Popular in | October |
Cheapest in | February |
Average price | $493 |
Good round-trip deal | $507 or less |
Good one-way deal | $369 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Kentucky 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 November 9, 2026.
Use the filters below to find and compare flights from Boston to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Wed 12/30
8:45 am-3:35 pm
1 stop6h 50m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$204
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Tue 11/17
11:20 am-8:40 pm
2 stops9h 20m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$208
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Fri 12/11
12:55 pm-10:15 pm
2 stops9h 20m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$219
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Tue 12/8
1:20 pm-9:55 pm
2 stops8h 35m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Sun 12/13
7:25 am-4:35 pm
2 stops9h 10m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Thu 3/18
12:02 pm-5:09 pm
2 stops29h 07m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Tue 11/24
7:00 am-1:35 pm
1 stop6h 35m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
BostonLexington
BOS Boston Logan Intl - LEX Lexington Blue Grass
BOSLEX
Boston Logan Intl
Mon 12/7
2:54 pm-9:28 pm
1 stop6h 34m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$289
BostonLexington
BOS Boston Logan Intl - LEX Lexington Blue Grass
BOSLEX
Boston Logan Intl
Tue 12/1
9:41 am-3:39 pm
1 stop5h 58m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$289
Quickest round-trip
BostonLexington
BOS Boston Logan Intl - LEX Lexington Blue Grass
BOSLEX
Boston Logan Intl
Thu 12/17
6:00 pm-11:10 pm
1 stop5h 10m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$289
Showing 1-10 of 42 resultsSorted by cheapest first
Best time to book a flight from Boston to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Boston with our price prediction graph.
BOS-LEX
BOS-SDF
BOS-OWB
BOS-PAH
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 Boston to Kentucky
BOS-USKY
BOS-LEX
BOS-SDF
BOS-OWB
BOS-PAH
What is the cheapest month to book a flight from Boston to Kentucky?
Currently, February is the cheapest month in which you can book a flight from Boston to Kentucky (average of $397). Flying from Boston to Kentucky in October is currently the most expensive (average of $558). 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 BOS to KY?
Find hourly flight availability from Boston to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 9, 2026.
When flying from Boston to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Boston to Kentucky
Explore weekly flight availability from Boston to Kentucky. 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 November 9, 2026.
The most flights from BOS to USKY are scheduled on a Sunday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Boston to Kentucky?
Airfare is typical for this route at the moment.
Boston to Kentucky flights typically cost between $445 and $602 in December.The cheapest round-trip price found within the last 5 days was $447 on Delta (Dec 3-Dec 8).
How far ahead should I book a flight from Boston to Kentucky?
The best time to book flights from Boston to Kentucky is 54 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated November 9, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Kentucky to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Boston to Kentucky. 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 Boston to Kentucky
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Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Kentucky by cabin class
Find flights from Boston to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Kentucky flights
Browse other Boston and Kentucky flight options. Last updated on November 9, 2026.
Popular flight searches
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Boston to Kentucky flights
Consider these flights traveling from Boston to Kentucky.
Top 5 airlines flying from Boston to Kentucky
Discover the top 5 airlines that operate flights from Boston to Kentucky. 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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$461 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$458 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$269 | Average$460 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$342 | Average$522 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$353 | Average$508 | FlexibilityNo cancel fee | On-time69% |