$33+ Cheap flights from Massachusetts 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Oct 13 — Oct 201
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts 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 Massachusetts to Kentucky
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Cheapest flights from Massachusetts to KentuckyExplore the most affordable flight options available from Massachusetts to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 13, 2026.
Explore the most affordable flight options available from Massachusetts to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 13, 2026.
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 10/269:30 pm -
Nonstop2h 20m
Fri 10/3010:43 am -
Nonstop2h 08m
Deal found 9/10![Allegiant Air logo]()
$69
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:53 pm -
Nonstop2h 20m
Fri 10/3010:43 am -
Nonstop2h 08m
Deal found 9/8![Allegiant Air logo]()
$76
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/29:04 pm -
Nonstop2h 20m
Fri 11/612:20 pm -
Nonstop2h 09m
Deal found 9/9![Allegiant Air logo]()
$95
This CheapOair deal was found by Cheapflights users on 9/9. 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 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 9/9![Allegiant Air logo]()
$98
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:04 pm -
Nonstop2h 20m
Fri 11/612:20 pm -
Nonstop2h 09m
Deal found 9/8![Allegiant Air logo]()
$106
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 10/269:30 pm -
Nonstop2h 20m
Mon 11/211:43 am -
Nonstop2h 08m
Deal found 9/10![Allegiant Air logo]()
$115
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:39 pm -
Nonstop2h 18m
Fri 9/187:20 am -
Nonstop2h 09m
Deal found 9/8![Allegiant Air logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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
Tue 10/208:30 am -
Nonstop2h 12m
Deal found 9/12![Allegiant Air logo]()
$123
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:02 am -
Nonstop2h 30m
Sun 11/17:30 am -
Nonstop2h 12m
Deal found 9/9![Allegiant Air logo]()
$130
This Booking.com deal was found by Cheapflights users on 9/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/311:32 am -
Nonstop2h 30m
Sat 11/76:00 am -
Nonstop2h 19m
Deal found 9/8![Allegiant Air logo]()
$140
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sun 12/1311:35 am -
Nonstop2h 36m
Sat 12/198:00 am -
Nonstop2h 11m
Deal found 9/10![Allegiant Air logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/149:09 am -
Nonstop2h 30m
Sun 11/156:00 am -
Nonstop2h 19m
Deal found 9/12![Allegiant Air logo]()
$150
Best flights from Massachusetts to KentuckyDiscover carefully curated flight deals from Massachusetts to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 13, 2026.
Discover carefully curated flight deals from Massachusetts to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 13, 2026.
This Breeze Airways deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:02 am -
1 stop3h 43m
Mon 11/910:25 am -
1 stop3h 28m
Deal found 9/12![Breeze Airways logo]()
$165
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/37:00 am -
2 stops9h 40m
Thu 11/58:10 am -
1 stop3h 55m
Deal found 9/10![Southwest logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 10/58:53 pm -
Nonstop2h 20m
Fri 10/96:36 am -
2 stops33h 52m
Deal found 9/7![Multiple Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/712:20 pm -
1 stop5h 18m
Wed 11/1111:43 am -
1 stop4h 09m
Deal found 9/10![Delta logo]()
$271
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Wed 10/146:00 am -
1 stop4h 29m
Fri 10/166:34 pm -
1 stop4h 25m
Deal found 9/8![United Airlines logo]()
$281
This JetBlue deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
Sat 10/176:03 am -
Nonstop2h 53m
Sat 10/2410:30 am -
1 stop5h 54m
Deal found 9/12![JetBlue logo]()
$364
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:16 pm -
1 stop16h 12m
Mon 10/267:30 pm -
1 stop20h 19m
Deal found 9/9![American Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:05 pm -
Nonstop2h 25m
Tue 11/175:35 am -
1 stop5h 10m
Deal found 9/12![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:15 pm -
1 stop5h 58m
Tue 10/279:33 am -
1 stop4h 54m
Deal found 9/9![Delta logo]()
$290
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Tue 11/107:41 pm -
1 stop4h 18m
Fri 11/135:45 am -
2 stops6h 41m
Deal found 9/8![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/196:00 am -
1 stop4h 49m
Sun 11/224:12 pm -
1 stop6h 47m
Deal found 9/12![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/199:37 am -
1 stop5h 41m
Mon 11/236:00 am -
2 stops7h 02m
Deal found 9/12![United Airlines logo]()
$306
This Southwest deal was found by Cheapflights users on 9/8. 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 10/55:50 pm -
1 stop6h 25m
Wed 10/217:10 am -
2 stops8h 30m
Deal found 9/8![Southwest logo]()
$314
This Breeze Airways deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:15 am -
1 stop9h 56m
Mon 9/2810:25 am -
1 stop3h 28m
Deal found 9/12![Breeze Airways logo]()
$366
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Wed 12/26:00 am -
2 stops8h 54m
Fri 12/411:18 am -
1 stop5h 16m
Deal found 9/8![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 9/8. 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 12/94:08 pm -
1 stop6h 24m
Mon 12/146:00 am -
2 stops8h 07m
Deal found 9/8![Delta logo]()
$320
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/54:20 pm -
1 stop7h 35m
Mon 11/98:15 pm -
Nonstop2h 25m
Deal found 9/10![Southwest logo]()
$327
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:16 pm -
2 stops20h 17m
Fri 10/26:28 pm -
2 stops21h 21m
Deal found 9/13![American Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/37:55 am -
1 stop5h 26m
Tue 10/68:50 am -
1 stop5h 17m
Deal found 9/10![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/8. 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 12/94:08 pm -
1 stop6h 24m
Wed 12/169:46 am -
1 stop4h 21m
Deal found 9/8![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 9/7. 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.
Thu 11/55:20 am -
Nonstop2h 50m
Sat 11/78:05 am -
1 stop9h 30m
Deal found 9/7![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/8. 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.
Thu 10/221:20 pm -
1 stop6h 20m
Mon 10/265:35 pm -
Nonstop2h 44m
Deal found 9/8![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:25 pm -
Nonstop2h 30m
Thu 12/102:45 pm -
1 stop5h 35m
Deal found 9/9![Southwest logo]()
$327
This United Airlines deal was found by Cheapflights users on 9/8. 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.
Sat 10/39:44 am -
1 stop7h 24m
Tue 10/67:25 pm -
1 stop4h 34m
Deal found 9/8![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/289:51 am -
1 stop6h 17m
Sat 12/510:13 am -
1 stop7h 24m
Deal found 9/7![American Airlines logo]()
$467
This Southwest deal was found by Cheapflights users on 9/8. 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 10/211:05 pm -
2 stops7h 35m
Sat 10/246:00 pm -
Nonstop2h 40m
Deal found 9/8![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:39 am -
1 stop4h 01m
Sun 11/17:59 pm -
1 stop5h 21m
Deal found 9/9![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:38 pm -
1 stop7h 53m
Sun 10/46:00 am -
1 stop3h 42m
Deal found 9/9![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 9/7. 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.
Thu 11/1911:20 am -
2 stops8h 00m
Mon 11/238:15 pm -
Nonstop2h 25m
Deal found 9/7![Southwest logo]()
$332
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 1/155:04 pm -
1 stop7h 10m
Sun 1/176:00 am -
2 stops6h 49m
Deal found 9/12![United Airlines logo]()
$343
Last-minute flights from Massachusetts to KentuckyDiscover last-minute flight deals from Massachusetts to Kentucky. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Kentucky. Data last updated September 13, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:39 pm -
Nonstop2h 18m
Fri 9/187:20 am -
Nonstop2h 09m
Deal found 9/8![Allegiant Air logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:35 pm -
Nonstop2h 26m
Wed 9/308:30 am -
Nonstop2h 12m
Deal found 9/8![Allegiant Air logo]()
$193
This Cheapflightsfares deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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
Tue 10/208:30 am -
Nonstop2h 12m
Deal found 9/12![Allegiant Air logo]()
$123
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/10![Allegiant Air logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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
Sun 10/117:15 am -
Nonstop2h 12m
Deal found 9/10![Allegiant Air logo]()
$181
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:53 pm -
Nonstop2h 20m
Fri 10/3010:43 am -
Nonstop2h 08m
Deal found 9/8![Allegiant Air logo]()
$76
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Fri 10/239:27 pm -
Nonstop2h 20m
Fri 10/3010:43 am -
Nonstop2h 08m
Deal found 9/10![Allegiant Air logo]()
$120
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 10/269:30 pm -
Nonstop2h 20m
Fri 10/3010:43 am -
Nonstop2h 08m
Deal found 9/10![Allegiant Air logo]()
$69
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 10/269:30 pm -
Nonstop2h 20m
Mon 11/211:43 am -
Nonstop2h 08m
Deal found 9/10![Allegiant Air logo]()
$115
This Booking.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:32 am -
Nonstop2h 30m
Tue 11/38:30 am -
Nonstop2h 12m
Deal found 9/12![Allegiant Air logo]()
$163
This CheapOair deal was found by Cheapflights users on 9/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:04 pm -
Nonstop2h 20m
Fri 11/612:20 pm -
Nonstop2h 09m
Deal found 9/8![Allegiant Air logo]()
$106
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:02 am -
Nonstop2h 30m
Sun 11/17:30 am -
Nonstop2h 12m
Deal found 9/9![Allegiant Air logo]()
$130
One-way flights from Massachusetts to KentuckySearch for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
Search for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:53 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Allegiant Air logo]()
$33
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Mon 10/269:30 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Allegiant Air logo]()
$37
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Mon 11/99:51 pm -
Nonstop2h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$50
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:48 pm -
Nonstop2h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$56
This Mytrip deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/79:09 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Allegiant Air logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:20 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Allegiant Air logo]()
$60
This Super.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Sat 10/312:32 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:48 pm -
Nonstop2h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/1210:03 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Allegiant Air logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:02 am -
1 stop3h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Breeze Airways logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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 11/311:32 am -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Allegiant Air logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sun 9/2010:15 am -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Allegiant Air logo]()
$83
Find flight deals from Massachusetts to Kentucky
Keep the following information in mind while searching for Massachusetts to Kentucky flight deals. Data was last updated September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $69 (CheapOair) |
One-way from | $33 (Super.com) |
Popular in | April |
Cheapest in | December |
Average price | $497 |
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 Massachusetts 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 13, 2026.
Use the filters below to find and compare flights from Massachusetts to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HartfordKnoxville
BDL Hartford Bradley Intl - TYS Knoxville McGhee Tyson
BDLTYS
Hartford Bradley Intl
Sat 2/27
6:00 am-4:25 pm
2 stops10h 25m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
HartfordLouisville
BDL Hartford Bradley Intl - SDF Louisville Intl
BDLSDF
Hartford Bradley Intl
Tue 10/13
7:00 am-2:41 pm
1 stop7h 41m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$136
HartfordLouisville
BDL Hartford Bradley Intl - SDF Louisville Intl
BDLSDF
Hartford Bradley Intl
Mon 10/5
7:04 pm-11:59 pm
1 stop4h 55m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$136
HartfordKnoxville
BDL Hartford Bradley Intl - TYS Knoxville McGhee Tyson
BDLTYS
Hartford Bradley Intl
Mon 11/23
10:37 am-8:54 pm
2 stops10h 17m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
HartfordLouisville
BDL Hartford Bradley Intl - SDF Louisville Intl
BDLSDF
Hartford Bradley Intl
Mon 11/2
12:55 pm-10:10 pm
2 stops9h 15m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$141
HartfordNashville
BDL Hartford Bradley Intl - BNA Nashville Intl
BDLBNA
Hartford Bradley Intl
Thu 3/4
5:48 am-9:18 am
1 stop4h 30m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
HartfordNashville
BDL Hartford Bradley Intl - BNA Nashville Intl
BDLBNA
Hartford Bradley Intl
Fri 3/5
2:20 pm-7:40 pm
1 stop6h 20m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
HartfordNashville
BDL Hartford Bradley Intl - BNA Nashville Intl
BDLBNA
Hartford Bradley Intl
Sat 3/6
5:48 am-9:18 am
1 stop4h 30m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$141
HartfordNashville
BDL Hartford Bradley Intl - BNA Nashville Intl
BDLBNA
Hartford Bradley Intl
Mon 10/19
7:20 pm-11:33 pm
1 stop5h 13m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$151
HartfordNashville
BDL Hartford Bradley Intl - BNA Nashville Intl
BDLBNA
Hartford Bradley Intl
Fri 1/1
6:00 am-9:46 am
1 stop4h 46m
Nashville Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$151
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Massachusetts with our price prediction graph.
ALB-BNA
BOS-TYS
BDL-SDF
BDL-TYS
BDL-BNA
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 Massachusetts to Kentucky
USMA-USKY
ALB-BNA
BOS-TYS
BDL-SDF
BDL-TYS
What is the cheapest month to book a flight from Massachusetts to Kentucky?
Currently, December is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $382). Flying from Massachusetts to Kentucky in April is currently the most expensive (average of $522). 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 MA to KY?
Find hourly flight availability from Massachusetts 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 13, 2026.
When flying from Massachusetts 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 Massachusetts to Kentucky?
Airfare is below average for this route at the moment.
Massachusetts to Kentucky flights typically cost between $450 and $553 in December.The cheapest round-trip price found within the last 5 days was $313 on American Airlines (Dec 2-Dec 5).
How far ahead should I book a flight from Massachusetts to Kentucky?
The best time to book flights from Massachusetts to Kentucky is 73 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 13, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Kentucky have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
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 Massachusetts 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 Massachusetts 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 Massachusetts to Kentucky by cabin class
Find flights from Massachusetts to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Kentucky flights
Browse other Massachusetts and Kentucky flight options. Last updated on September 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Kentucky
Find the right flight back to Massachusetts after your stay in Kentucky
Massachusetts to Kentucky flights
Consider these flights traveling from Massachusetts to Kentucky.
Top 5 airlines flying from Massachusetts to Kentucky
Discover the top 5 airlines that operate flights from Massachusetts 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 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$489 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$441 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$269 | Average$455 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$342 | Average$518 | FlexibilityNo cancel fee | On-time63% |