$43+ Cheap flights from Kentucky to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Massachusetts with Cheapflights
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Cheapest flights from Kentucky to MassachusettsExplore the most affordable flight options available from Kentucky to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
Explore the most affordable flight options available from Kentucky to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
This Trip.com deal was found by Cheapflights users on 8/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:20 am -
Nonstop2h 09m
Mon 9/1412:39 pm -
Nonstop2h 18m
Deal found 8/9![Allegiant Air logo]()
$79
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/2112:39 pm -
Nonstop2h 18m
Deal found 8/7![Allegiant Air logo]()
$91
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:00 am -
Nonstop2h 09m
Mon 8/3110:59 am -
Nonstop2h 21m
Deal found 8/5![Allegiant Air logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:35 am -
Nonstop2h 10m
Mon 8/317:35 am -
Nonstop2h 20m
Deal found 8/5![Breeze Airways logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 8/2410:35 am -
Nonstop2h 10m
Mon 8/317:35 am -
Nonstop2h 20m
Deal found 8/8![Breeze Airways logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:35 am -
Nonstop2h 10m
Fri 8/287:35 am -
Nonstop2h 20m
Deal found 8/5![Breeze Airways logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:30 am -
Nonstop2h 09m
Mon 8/3110:59 am -
Nonstop2h 21m
Deal found 8/5![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:35 am -
Nonstop2h 10m
Mon 9/77:35 am -
Nonstop2h 20m
Deal found 8/6![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:40 pm -
Nonstop2h 02m
Sun 8/307:00 am -
Nonstop2h 07m
Deal found 8/6![Breeze Airways logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Thu 8/278:40 pm -
Nonstop2h 02m
Sun 8/307:00 am -
Nonstop2h 07m
Deal found 8/8![Breeze Airways logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Tue 9/88:40 pm -
Nonstop2h 02m
Mon 9/283:16 pm -
1 stop28h 20m
Deal found 8/9![Multiple Airlines logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:40 pm -
Nonstop2h 02m
Tue 9/87:00 am -
Nonstop2h 07m
Deal found 8/5![Breeze Airways logo]()
$167
Best flights from Kentucky to MassachusettsDiscover carefully curated flight deals from Kentucky to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
Discover carefully curated flight deals from Kentucky to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/9. 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.
Thu 9/106:50 pm -
Nonstop2h 35m
Mon 9/145:25 am -
Nonstop2h 35m
Deal found 8/9![Southwest logo]()
$221
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:10 am -
Nonstop2h 32m
Mon 9/146:19 am -
1 stop8h 09m
Deal found 8/5![JetBlue logo]()
$254
This United Airlines deal was found by Cheapflights users on 8/8. 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 9/263:05 pm -
2 stops7h 54m
Mon 9/286:00 am -
1 stop4h 31m
Deal found 8/8![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 8/6. 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.
Sun 9/65:50 pm -
1 stop6h 08m
Mon 9/75:30 am -
1 stop4h 24m
Deal found 8/6![Delta logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/149:42 pm -
2 stops19h 26m
Fri 9/186:02 am -
1 stop3h 43m
Deal found 8/9![Breeze Airways logo]()
$314
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 10/2410:25 am -
Nonstop2h 35m
Wed 10/285:45 pm -
Nonstop2h 45m
Deal found 8/10![Southwest logo]()
$221
This United Airlines deal was found by Cheapflights users on 8/9. 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.
Mon 8/316:42 pm -
1 stop4h 17m
Sun 9/610:33 am -
2 stops7h 59m
Deal found 8/9![United Airlines logo]()
$266
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:00 am -
Nonstop2h 30m
Sat 9/121:30 pm -
Nonstop2h 49m
Deal found 8/5![JetBlue logo]()
$267
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 9/167:05 am -
2 stops8h 55m
Sat 9/265:00 am -
1 stop7h 05m
Deal found 8/9![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Wed 8/2611:18 am -
1 stop6h 02m
Thu 9/310:33 am -
2 stops6h 57m
Deal found 8/7![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 8/5. 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 9/115:00 pm -
1 stop6h 59m
Sun 9/135:30 am -
1 stop4h 14m
Deal found 8/5![Delta logo]()
$293
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:27 pm -
1 stop8h 28m
Mon 11/28:00 am -
1 stop6h 32m
Deal found 8/5![JetBlue logo]()
$277
This Southwest deal was found by Cheapflights users on 8/9. 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.
Mon 10/195:30 pm -
1 stop3h 30m
Thu 10/225:35 pm -
1 stop6h 30m
Deal found 8/9![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 8/6. 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 9/94:01 pm -
2 stops6h 58m
Sat 9/123:11 pm -
2 stops7h 26m
Deal found 8/6![United Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 8/5. 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 8/313:25 pm -
1 stop5h 05m
Tue 9/16:00 am -
1 stop4h 32m
Deal found 8/5![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 9/95:40 am -
2 stops9h 55m
Wed 9/1612:50 pm -
1 stop7h 25m
Deal found 8/9![Southwest logo]()
$264
This Delta deal was found by Cheapflights users on 8/5. 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.
Wed 8/267:55 am -
1 stop4h 05m
Thu 9/31:54 pm -
1 stop5h 36m
Deal found 8/5![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/5. 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 8/295:45 am -
1 stop4h 33m
Sat 9/56:01 am -
1 stop7h 17m
Deal found 8/5![United Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 8/5. 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.
Wed 8/266:00 am -
1 stop6h 48m
Sat 8/295:30 am -
1 stop4h 24m
Deal found 8/5![Delta logo]()
$299
This JetBlue deal was found by Cheapflights users on 8/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/42:30 pm -
1 stop8h 28m
Sun 9/65:07 pm -
1 stop6h 30m
Deal found 8/7![JetBlue logo]()
$329
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:45 pm -
2 stops8h 45m
Sat 9/125:00 am -
1 stop6h 55m
Deal found 8/5![Southwest logo]()
$278
This United Airlines deal was found by Cheapflights users on 8/6. 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 9/191:49 pm -
2 stops10h 10m
Wed 9/236:10 am -
1 stop4h 08m
Deal found 8/6![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 8/7. 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.
Thu 9/35:15 pm -
1 stop5h 18m
Mon 9/76:00 am -
1 stop4h 58m
Deal found 8/7![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/9. 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.
Wed 9/28:50 am -
1 stop6h 10m
Sun 9/67:45 am -
Nonstop2h 40m
Deal found 8/9![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Fri 9/116:02 pm -
1 stop5h 28m
Sun 9/135:45 am -
1 stop4h 52m
Deal found 8/7![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 8/6. 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.
Tue 10/206:55 am -
1 stop5h 27m
Sat 10/241:05 pm -
1 stop4h 06m
Deal found 8/6![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:50 am -
1 stop4h 50m
Wed 9/91:20 pm -
2 stops7h 35m
Deal found 8/5![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/109:45 am -
2 stops7h 03m
Sun 9/135:45 am -
1 stop4h 52m
Deal found 8/5![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 8/6. 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 10/233:54 pm -
1 stop7h 26m
Sun 10/255:30 am -
1 stop6h 28m
Deal found 8/6![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:00 pm -
1 stop4h 15m
Tue 10/611:30 am -
2 stops8h 40m
Deal found 8/5![Southwest logo]()
$304
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated August 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 8/2410:35 am -
Nonstop2h 10m
Mon 8/317:35 am -
Nonstop2h 20m
Deal found 8/8![Breeze Airways logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:35 am -
Nonstop2h 10m
Fri 8/287:35 am -
Nonstop2h 20m
Deal found 8/5![Breeze Airways logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:30 am -
Nonstop2h 09m
Mon 8/3110:59 am -
Nonstop2h 21m
Deal found 8/5![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:40 pm -
Nonstop2h 02m
Sun 8/307:00 am -
Nonstop2h 07m
Deal found 8/6![Breeze Airways logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 8/8. 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.
Thu 8/278:40 pm -
Nonstop2h 02m
Sun 8/307:00 am -
Nonstop2h 07m
Deal found 8/8![Breeze Airways logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:00 am -
Nonstop2h 09m
Mon 8/3110:59 am -
Nonstop2h 21m
Deal found 8/5![Allegiant Air logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:35 am -
Nonstop2h 10m
Mon 8/317:35 am -
Nonstop2h 20m
Deal found 8/5![Breeze Airways logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:35 am -
Nonstop2h 10m
Mon 9/77:35 am -
Nonstop2h 20m
Deal found 8/6![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:40 pm -
Nonstop2h 02m
Tue 9/87:00 am -
Nonstop2h 07m
Deal found 8/5![Breeze Airways logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Tue 9/88:40 pm -
Nonstop2h 02m
Mon 9/283:16 pm -
1 stop28h 20m
Deal found 8/9![Multiple Airlines logo]()
$159
This Trip.com deal was found by Cheapflights users on 8/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:20 am -
Nonstop2h 09m
Mon 9/1412:39 pm -
Nonstop2h 18m
Deal found 8/9![Allegiant Air logo]()
$79
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:20 am -
Nonstop2h 09m
Mon 9/2112:39 pm -
Nonstop2h 18m
Deal found 8/7![Allegiant Air logo]()
$91
One-way flights from Kentucky to MassachusettsSearch for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/7. 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.
Sat 9/129:30 am -
Nonstop2h 15m
Deal found 8/7![Allegiant Air logo]()
$43
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:20 pm -
Nonstop2h 09m
Deal found 8/7![Allegiant Air logo]()
$47
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:10 am -
Nonstop2h 15m
Deal found 8/6![Allegiant Air logo]()
$51
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:22 pm -
Nonstop2h 08m
Deal found 8/5![Allegiant Air logo]()
$52
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:30 am -
Nonstop2h 15m
Deal found 8/5![Allegiant Air logo]()
$55
This Super.com deal was found by Cheapflights users on 8/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:00 am -
Nonstop2h 09m
Deal found 8/6![Allegiant Air logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:22 pm -
Nonstop2h 08m
Deal found 8/5![Allegiant Air logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:30 am -
Nonstop2h 15m
Deal found 8/5![Allegiant Air logo]()
$60
This Trip.com deal was found by Cheapflights users on 8/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:00 am -
Nonstop2h 09m
Deal found 8/5![Allegiant Air logo]()
$71
This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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.
Fri 8/218:30 am -
Nonstop2h 09m
Deal found 8/9![Allegiant Air logo]()
$74
This Breeze Airways deal was found by Cheapflights users on 8/5. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm -
Nonstop2h 02m
Deal found 8/5![Breeze Airways logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Thu 10/226:34 pm -
1 stop24h 26m
Deal found 8/9![Frontier logo]()
$75
Find flight deals from Kentucky to Massachusetts
Keep the following information in mind while searching for Kentucky to Massachusetts flight deals. Data was last updated August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $79 (Trip.com) |
One-way from | $43 (Kiwi.com) |
Popular in | April |
Cheapest in | October |
Average price | $408 |
Good round-trip deal | $441 or less |
Good one-way deal | $277 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Massachusetts 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 2,558,603 searches. Data last updated August 10, 2026.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Thu 9/10
6:50 pm-10:25 pm
Nonstop2h 35m
Boston Logan Intl
Mon 9/14
5:25 am-7:00 am
Nonstop2h 35m
$221
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Sat 10/24
10:25 am-2:00 pm
Nonstop2h 35m
Boston Logan Intl
Wed 10/28
5:45 pm-7:30 pm
Nonstop2h 45m
$221
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Sat 9/12
9:10 am-12:42 pm
Nonstop2h 32m
Boston Logan Intl
Mon 9/14
6:19 am-1:28 pm
1 stop8h 09m
$254
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 9/16
7:05 am-4:00 pm
2 stops8h 55m
Boston Logan Intl
Sat 9/26
5:00 am-12:05 pm
1 stop7h 05m
$257
CincinnatiAlbany
CVG Cincinnati Cinci./N. Kentucky - ALB Albany Intl
CVGALB
Cincinnati Cinci./N. Kentucky
Mon 10/19
5:30 pm-9:00 pm
1 stop3h 30m
Albany Intl
Thu 10/22
5:35 pm-12:05 am
1 stop6h 30m
$258
CincinnatiAlbany
CVG Cincinnati Cinci./N. Kentucky - ALB Albany Intl
CVGALB
Cincinnati Cinci./N. Kentucky
Wed 9/9
5:40 am-3:35 pm
2 stops9h 55m
Albany Intl
Wed 9/16
12:50 pm-8:15 pm
1 stop7h 25m
$264
NashvilleHartford
BNA Nashville Intl - BDL Hartford Bradley Intl
BNABDL
Nashville Intl
Sat 9/26
3:05 pm-11:59 pm
2 stops7h 54m
Hartford Bradley Intl
Mon 9/28
6:00 am-9:31 am
1 stop4h 31m
$266
NashvilleHartford
BNA Nashville Intl - BDL Hartford Bradley Intl
BNABDL
Nashville Intl
Mon 8/31
6:42 pm-11:59 pm
1 stop4h 17m
Hartford Bradley Intl
Sun 9/6
10:33 am-5:32 pm
2 stops7h 59m
$266
NashvilleHartford
BNA Nashville Intl - BDL Hartford Bradley Intl
BNABDL
Nashville Intl
Wed 8/26
11:18 am-6:20 pm
1 stop6h 02m
Hartford Bradley Intl
Thu 9/3
10:33 am-4:30 pm
2 stops6h 57m
$266
NashvilleBoston
BNA Nashville Intl - BOS Boston Logan Intl
BNABOS
Nashville Intl
Sat 9/5
9:00 am-12:30 pm
Nonstop2h 30m
Boston Logan Intl
Sat 9/12
1:30 pm-3:19 pm
Nonstop2h 49m
$267
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Kentucky with our price prediction graph.
CVG-BDL
TYS-BOS
BNA-BOS
SDF-BDL
BNA-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Massachusetts
USKY-USMA
CVG-BDL
TYS-BOS
BNA-BOS
SDF-BDL
What is the cheapest month to book a flight from Kentucky to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $357). Flying from Kentucky to Massachusetts in April is currently the most expensive (average of $495). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from KY to MA?
Find hourly flight availability from Kentucky to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 10, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Massachusetts as you normally would.
Weekly flight availability from Kentucky to Massachusetts
Explore weekly flight availability from Kentucky to Massachusetts. 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 August 10, 2026.
The most flights from USKY to USMA are scheduled on a Friday (7 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Kentucky to Massachusetts?
Airfare is below average for this route at the moment.
Kentucky to Massachusetts flights typically cost between $371 and $464 in September.The cheapest round-trip price found within the last 5 days was $257 on Southwest (Sep 16-Sep 26).
How far ahead should I book a flight from Kentucky to Massachusetts?
The price you pay for your flight from Kentucky to Massachusetts may vary depending on when you book. For the best chance of a lower fare, look to book 73 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated August 10, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Kentucky to Massachusetts by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Massachusetts. 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 Kentucky to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Massachusetts by cabin class
Find flights from Kentucky to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Massachusetts flights
Browse other Kentucky and Massachusetts flight options. Last updated on August 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Kentucky after your stay in Massachusetts
Kentucky to Massachusetts flights
Consider these flights traveling from Kentucky to Massachusetts.
Top 4 airlines flying from Kentucky to Massachusetts
Discover the top 4 airlines that operate flights from Kentucky to Massachusetts. 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 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$396 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$204 | Average$389 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$293 | Average$413 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$437 | FlexibilityNo cancel fee | On-time69% |