$60+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Kentucky with Cheapflights
1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Kentucky
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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 September 22, 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 September 22, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:09 am -
Nonstop2h 30m
Sat 11/146:00 am -
Nonstop2h 19m
Deal found 9/21![Allegiant Air logo]()
$127
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:32 pm -
Nonstop2h 30m
Sat 10/106:00 am -
Nonstop2h 12m
Deal found 9/17![Allegiant Air logo]()
$141
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:09 am -
Nonstop2h 30m
Sun 11/156:00 am -
Nonstop2h 19m
Deal found 9/19![Allegiant Air logo]()
$145
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:31 am -
Nonstop2h 32m
Sun 12/206:30 am -
Nonstop2h 11m
Deal found 9/21![Allegiant Air logo]()
$157
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:32 am -
Nonstop2h 30m
Tue 11/38:30 am -
Nonstop2h 12m
Deal found 9/20![Allegiant Air logo]()
$173
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.
Sat 10/312:32 pm -
Nonstop2h 30m
Sat 10/176:00 am -
Nonstop2h 12m
Deal found 9/19![Allegiant Air logo]()
$184
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:19 am -
Nonstop2h 30m
Sun 11/156:00 am -
Nonstop2h 19m
Deal found 9/19![Allegiant Air logo]()
$209
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:25 am -
Nonstop2h 51m
Thu 10/82:27 pm -
1 stop9h 06m
Deal found 9/17![JetBlue logo]()
$274
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.
Tue 10/209:26 am -
1 stop6h 23m
Tue 10/2711:12 am -
1 stop4h 42m
Deal found 9/18![American Airlines logo]()
$275
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:59 pm -
Nonstop2h 50m
Sat 10/243:38 pm -
Nonstop3h 21m
Deal found 9/18![JetBlue logo]()
$276
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 pm -
Nonstop3h 08m
Tue 11/244:05 pm -
Nonstop2h 30m
Deal found 9/22![JetBlue logo]()
$277
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:08 am -
1 stop9h 16m
Mon 12/74:48 pm -
Nonstop2h 35m
Deal found 9/18![Multiple Airlines logo]()
$278
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 September 22, 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 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.
Wed 11/41:10 pm -
1 stop5h 35m
Sat 11/72:55 pm -
2 stops6h 10m
Deal found 9/17![Southwest logo]()
$301
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:25 am -
Nonstop2h 49m
Wed 10/72:25 pm -
1 stop6h 52m
Deal found 9/19![JetBlue logo]()
$325
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.
Thu 10/157:01 am -
1 stop7h 31m
Wed 10/215:00 am -
1 stop6h 48m
Deal found 9/21![United Airlines logo]()
$334
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:50 am -
1 stop5h 46m
Tue 10/201:22 pm -
1 stop5h 43m
Deal found 9/21![Delta logo]()
$339
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:22 pm -
1 stop5h 47m
Sat 10/317:01 am -
2 stops8h 46m
Deal found 9/21![American Airlines logo]()
$480
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.
Sat 10/2412:00 pm -
2 stops8h 10m
Wed 10/285:30 am -
1 stop6h 00m
Deal found 9/19![Southwest logo]()
$310
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:00 am -
1 stop5h 09m
Mon 11/161:51 pm -
1 stop6h 32m
Deal found 9/19![Delta logo]()
$339
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 10/2412:00 pm -
2 stops8h 10m
Tue 10/2711:50 am -
1 stop5h 45m
Deal found 9/21![Southwest logo]()
$310
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 12/44:45 pm -
1 stop5h 47m
Sun 12/67:00 am -
2 stops8h 52m
Deal found 9/20![United Airlines logo]()
$344
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:30 am -
1 stop7h 06m
Mon 11/93:35 pm -
1 stop6h 10m
Deal found 9/19![Delta logo]()
$339
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.
Sun 10/255:30 am -
1 stop4h 56m
Tue 10/276:00 am -
2 stops11h 57m
Deal found 9/17![United Airlines logo]()
$360
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 10/2412:00 pm -
2 stops8h 10m
Mon 10/267:00 pm -
1 stop4h 10m
Deal found 9/17![Southwest logo]()
$330
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:50 pm -
1 stop5h 22m
Tue 1/1210:05 am -
1 stop6h 13m
Deal found 9/21![Delta logo]()
$339
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.
Sat 10/245:35 am -
1 stop4h 45m
Sat 10/242:35 pm -
2 stops6h 35m
Deal found 9/20![Southwest logo]()
$340
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:00 am -
1 stop5h 08m
Sun 12/136:05 am -
1 stop5h 21m
Deal found 9/17![Delta logo]()
$345
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.
Sat 10/2412:36 pm -
2 stops8h 25m
Wed 10/285:45 am -
2 stops6h 41m
Deal found 9/21![United Airlines logo]()
$382
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.
Fri 11/64:41 pm -
1 stop8h 18m
Sun 11/86:40 am -
1 stop6h 51m
Deal found 9/19![American Airlines logo]()
$497
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 10/282:50 pm -
2 stops5h 50m
Sun 11/18:05 am -
1 stop8h 05m
Deal found 9/19![Southwest logo]()
$341
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.
Thu 10/2910:15 am -
1 stop5h 50m
Sun 11/17:30 am -
Nonstop2h 40m
Deal found 9/18![Delta logo]()
$356
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 10/315:30 am -
1 stop18h 29m
Mon 11/26:00 am -
1 stop17h 59m
Deal found 9/19![United Airlines logo]()
$403
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 10/65:35 am -
2 stops6h 55m
Tue 10/612:45 pm -
2 stops7h 35m
Deal found 9/21![Southwest logo]()
$355
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:55 am -
2 stops6h 58m
Tue 10/206:24 am -
1 stop4h 34m
Deal found 9/21![American Airlines logo]()
$523
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/178:25 pm -
Nonstop3h 08m
Sun 12/205:45 pm -
Nonstop2h 38m
Deal found 9/19![Delta 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.
Sun 10/185:45 am -
1 stop4h 52m
Fri 10/235:45 am -
2 stops6h 58m
Deal found 9/17![United Airlines logo]()
$412
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.
Thu 11/123:30 pm -
2 stops8h 55m
Mon 11/163:50 pm -
1 stop6h 25m
Deal found 9/19![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.
Tue 10/1311:33 am -
1 stop7h 18m
Sat 10/1712:13 pm -
1 stop5h 29m
Deal found 9/19![American Airlines logo]()
$538
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:15 am -
1 stop4h 47m
Tue 10/63:51 pm -
1 stop7h 43m
Deal found 9/17![Delta logo]()
$369
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 12/45:00 pm -
2 stops6h 59m
Sun 12/66:20 am -
1 stop6h 07m
Deal found 9/19![United Airlines logo]()
$421
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.
Sun 1/108:50 am -
2 stops10h 50m
Sat 1/166:55 am -
2 stops7h 05m
Deal found 9/17![Southwest logo]()
$378
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 11/258:18 am -
1 stop8h 30m
Sat 11/284:18 pm -
1 stop6h 08m
Deal found 9/18![American Airlines logo]()
$571
Last-minute flights from Boston to KentuckyDiscover last-minute flight deals from Boston to Kentucky. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Kentucky. Data last updated September 22, 2026 and is based on user searches.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:32 pm -
Nonstop2h 30m
Sat 10/106:00 am -
Nonstop2h 12m
Deal found 9/17![Allegiant Air logo]()
$141
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.
Sat 10/312:32 pm -
Nonstop2h 30m
Sat 10/176:00 am -
Nonstop2h 12m
Deal found 9/19![Allegiant Air logo]()
$184
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:25 am -
Nonstop2h 51m
Thu 10/82:27 pm -
1 stop9h 06m
Deal found 9/17![JetBlue logo]()
$274
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
Nonstop2h 51m
Tue 10/136:00 am -
Nonstop2h 34m
Deal found 9/17![JetBlue logo]()
$279
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.
Wed 10/145:45 am -
1 stop4h 52m
Sat 10/174:16 pm -
1 stop6h 29m
Deal found 9/17![United Airlines logo]()
$227
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.
Tue 10/209:26 am -
1 stop6h 23m
Tue 10/2711:12 am -
1 stop4h 42m
Deal found 9/18![American Airlines logo]()
$275
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 10/205:35 am -
2 stops6h 55m
Wed 10/2111:55 am -
1 stop5h 40m
Deal found 9/21![Southwest logo]()
$280
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:03 am -
Nonstop2h 53m
Thu 10/226:00 am -
Nonstop2h 34m
Deal found 9/21![JetBlue logo]()
$283
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:59 pm -
Nonstop2h 50m
Sat 10/243:38 pm -
Nonstop3h 21m
Deal found 9/18![JetBlue logo]()
$276
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:47 am -
1 stop8h 56m
Sat 11/148:50 am -
Nonstop2h 25m
Deal found 9/18![Multiple Airlines logo]()
$282
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:32 am -
Nonstop2h 30m
Tue 11/38:30 am -
Nonstop2h 12m
Deal found 9/20![Allegiant Air logo]()
$173
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:32 am -
Nonstop2h 30m
Sun 11/17:30 am -
Nonstop2h 12m
Deal found 9/21![Allegiant Air logo]()
$226
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 September 22, 2026.
Search for one-way flight options from Boston to Kentucky. 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 9/21. 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.
Sat 10/312:32 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Allegiant Air logo]()
$60
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:31 am -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Allegiant Air logo]()
$92
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 10/2910:32 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Allegiant Air logo]()
$115
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 11/1210:19 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Allegiant Air logo]()
$121
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1911:01 am -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Allegiant Air logo]()
$124
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.
Sat 9/2612:35 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Allegiant Air logo]()
$126
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 11/105:30 am -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$133
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.
Wed 11/49:12 am -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$136
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:50 pm -
1 stop7h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$138
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 12/128:10 am -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$139
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 10/206:45 am -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$141
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:47 am -
2 stops20h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$141
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (CheapOair) |
One-way from | $60 (Kiwi.com) |
Popular in | April |
Cheapest in | December |
Average price | $506 |
Good round-trip deal | $482 or less |
Good one-way deal | $308 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 September 22, 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
BostonKnoxville
BOS Boston Logan Intl - TYS Knoxville McGhee Tyson
BOSTYS
Boston Logan Intl
Wed 11/4
9:12 am-4:59 pm
1 stop7h 47m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$136
BostonKnoxville
BOS Boston Logan Intl - TYS Knoxville McGhee Tyson
BOSTYS
Boston Logan Intl
Wed 10/28
4:15 pm-9:05 pm
1 stop4h 50m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$136
BostonKnoxville
BOS Boston Logan Intl - TYS Knoxville McGhee Tyson
BOSTYS
Boston Logan Intl
Tue 10/6
8:00 am-3:47 pm
1 stop7h 47m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$146
BostonNashville
BOS Boston Logan Intl - BNA Nashville Intl
BOSBNA
Boston Logan Intl
Mon 11/9
5:40 pm-11:12 pm
1 stop6h 32m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$168
BostonNashville
BOS Boston Logan Intl - BNA Nashville Intl
BOSBNA
Boston Logan Intl
Fri 10/23
4:15 pm-10:18 pm
1 stop7h 03m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$171
BostonNashville
BOS Boston Logan Intl - BNA Nashville Intl
BOSBNA
Boston Logan Intl
Wed 10/14
5:35 am-11:30 am
2 stops6h 55m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Wed 10/14
6:30 pm-11:05 pm
1 stop4h 35m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Sat 11/14
7:25 am-12:55 pm
1 stop5h 30m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
BostonCincinnati
BOS Boston Logan Intl - CVG Cincinnati Cinci./N. Kentucky
BOSCVG
Boston Logan Intl
Wed 11/18
5:20 am-3:25 pm
2 stops10h 05m
Cincinnati Cinci./N. Kentucky
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
BostonNashville
BOS Boston Logan Intl - BNA Nashville Intl
BOSBNA
Boston Logan Intl
Sun 10/25
5:10 am-6:55 am
Nonstop2h 45m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$189
Showing 1-10 of 60 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-BNA
BOS-PAH
BOS-TRI
BOS-EVV
BOS-LEX
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-BNA
BOS-PAH
BOS-TRI
BOS-EVV
What is the cheapest month to book a flight from Boston to Kentucky?
Currently, December is the cheapest month in which you can book a flight from Boston to Kentucky (average of $384). Flying from Boston to Kentucky in April is currently the most expensive (average of $527). 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 September 22, 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.
How much does it cost to fly round-trip from Boston to Kentucky?
Airfare is below average for this route at the moment.
Boston to Kentucky flights typically cost between $428 and $644 in November.The cheapest round-trip price found within the last 5 days was $313 on American Airlines (Nov 12-Nov 14).
How far ahead should I book a flight from Boston to Kentucky?
The best time to book flights from Boston to Kentucky is 90 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 September 22, 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
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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
See prices for flight routes from nearby airports that may be better suited for you.
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 September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$264 | Average$452 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$268 | Average$441 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$342 | Average$502 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$353 | Average$509 | FlexibilityNo cancel fee | On-time69% |