$75+ Cheap flights from Massachusetts to Kentucky
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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Mar 13 — Mar 201
1 adult, Economy
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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 February 11, 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 February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 6/197:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Fri 6/2610:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 2/10![Breeze Airways logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Fri 6/57:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 6/810:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 2/7![Breeze Airways logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 6/197:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 6/2910:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 2/10![Breeze Airways logo]()
$128
This Booking.com deal was found by Cheapflights users on 2/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Sun 3/86:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 4/210:36 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sun 4/57:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 2/9![Allegiant Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sat 5/306:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/9![Allegiant Air logo]()
$146
This Orbitz deal was found by Cheapflights users on 2/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:08 pm
BDL
- CVG
1 stop27h 12m
Multiple Airlines
Thu 5/79:12 pm
CVG
- BDL
Nonstop2h 02m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$147
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/269:28 am
BOS
- TYS
Nonstop2h 41m
Allegiant Air
Sun 3/16:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Sat 5/239:45 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sat 5/306:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/9![Allegiant Air logo]()
$152
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:27 am
BOS
- BNA
1 stop15h 21m
Spirit Airlines
Wed 3/182:27 pm
BNA
- BOS
1 stop8h 32m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$154
This Super.com deal was found by Cheapflights users on 2/8. 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 3/28:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Wed 3/46:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Deal found 2/8![JetBlue logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Tue 3/109:08 am
BOS
- BNA
Nonstop3h 04m
JetBlue
Thu 3/126:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Deal found 2/8![JetBlue logo]()
$156
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 February 11, 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 February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 4/210:36 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sun 4/57:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 2/9![Allegiant Air logo]()
$138
This Delta deal was found by Cheapflights users on 2/8. 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.
Sat 2/288:07 am
BOS
- BNA
Nonstop3h 13m
Delta
Tue 3/35:45 pm
BNA
- BOS
Nonstop2h 31m
Delta
Deal found 2/8![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 2/8. 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.
Tue 3/108:20 am
BOS
- BNA
Nonstop2h 55m
Southwest
Tue 3/177:35 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Deal found 2/8![Southwest logo]()
$162
This United Airlines deal was found by Cheapflights users on 2/7. 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.
Sat 3/75:45 am
BOS
- BNA
1 stop4h 37m
United Airlines
Thu 3/128:00 am
BNA
- BOS
1 stop6h 16m
United Airlines
Deal found 2/7![United Airlines logo]()
$177
This Priceline deal was found by Cheapflights users on 2/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/249:49 am
BDL
- CVG
1 stop11h 36m
Frontier
Sat 2/2811:15 am
CVG
- BDL
1 stop9h 05m
Frontier
Deal found 2/9![Frontier logo]()
$181
This JetBlue deal was found by Cheapflights users on 2/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:55 pm
BOS
- BNA
Nonstop3h 02m
JetBlue
Fri 3/206:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Deal found 2/9![JetBlue logo]()
$192
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:17 pm
ALB
- BNA
1 stop6h 25m
American Airlines
Tue 3/243:27 pm
BNA
- ALB
1 stop7h 17m
American Airlines
Deal found 2/10![American Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Wed 4/84:23 pm
BOS
- TYS
2 stops23h 18m
Multiple Airlines
Sun 4/126:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 2/196:00 am
BDL
- SDF
1 stop7h 26m
Breeze Airways
Sun 2/222:26 pm
SDF
- BDL
1 stop26h 42m
Breeze Airways
Deal found 2/8![Breeze Airways logo]()
$281
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:10 pm
BOS
- SDF
2 stops18h 11m
Spirit Airlines
Thu 3/123:33 pm
SDF
- BOS
1 stop8h 26m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 2/10. 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.
Thu 2/268:07 am
BOS
- BNA
Nonstop3h 13m
Delta
Sat 2/283:30 pm
BNA
- BOS
Nonstop2h 34m
Delta
Deal found 2/10![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 3/75:15 am
BOS
- BNA
1 stop5h 10m
Southwest
Mon 3/99:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Deal found 2/9![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 2/8. 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 2/247:45 am
BOS
- BNA
1 stop5h 43m
United Airlines
Wed 3/47:30 am
BNA
- BOS
2 stops8h 51m
United Airlines
Deal found 2/8![United Airlines logo]()
$187
This JetBlue deal was found by Cheapflights users on 2/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:45 pm
BOS
- BNA
Nonstop2h 49m
JetBlue
Tue 4/286:00 am
BNA
- BOS
Nonstop2h 29m
JetBlue
Deal found 2/10![JetBlue logo]()
$197
This American Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:17 pm
ALB
- BNA
1 stop6h 22m
American Airlines
Thu 3/125:00 am
BNA
- ALB
1 stop6h 07m
American Airlines
Deal found 2/8![American Airlines logo]()
$201
This United Airlines deal was found by Cheapflights users on 2/7. 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 4/12:37 pm
BOS
- BNA
1 stop5h 19m
United Airlines
Wed 4/87:25 am
BNA
- BOS
1 stop6h 23m
United Airlines
Deal found 2/7![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 2/9. 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 3/166:25 pm
BOS
- BNA
1 stop5h 35m
Southwest
Tue 3/177:35 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Deal found 2/9![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 2/8. 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.
Sun 4/266:00 am
ALB
- BNA
1 stop4h 06m
Delta
Tue 5/56:40 am
BNA
- ALB
1 stop4h 02m
Delta
Deal found 2/8![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Fri 2/277:00 am
BDL
- CVG
2 stops10h 32m
Multiple Airlines
Sat 2/287:04 pm
CVG
- BDL
1 stop18h 28m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$232
This United Airlines deal was found by Cheapflights users on 2/9. 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.
Wed 2/254:25 pm
BOS
- BNA
1 stop6h 28m
United Airlines
Tue 3/31:30 pm
BNA
- BOS
2 stops7h 21m
United Airlines
Deal found 2/9![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 2/8. 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.
Tue 4/286:00 pm
ALB
- BNA
1 stop5h 56m
Delta
Wed 4/296:29 am
BNA
- ALB
1 stop4h 44m
Delta
Deal found 2/8![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Multiple Airlines
Sun 4/1211:27 am
TYS
- BOS
2 stops46h 54m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$236
This United Airlines deal was found by Cheapflights users on 2/9. 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 4/276:05 am
ALB
- BNA
1 stop5h 31m
United Airlines
Wed 4/297:25 am
BNA
- ALB
1 stop6h 47m
United Airlines
Deal found 2/9![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 2/9. 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 4/106:04 pm
ALB
- BNA
1 stop6h 16m
Delta
Fri 4/175:25 am
BNA
- ALB
1 stop5h 48m
Delta
Deal found 2/9![Delta logo]()
$197
This Orbitz deal was found by Cheapflights users on 2/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:52 am
BDL
- CVG
1 stop14h 07m
Frontier
Thu 3/55:20 am
CVG
- BDL
1 stop11h 55m
Frontier
Deal found 2/8![Frontier logo]()
$264
This United Airlines deal was found by Cheapflights users on 2/7. 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.
Sat 5/305:04 pm
BDL
- BNA
1 stop5h 43m
United Airlines
Wed 6/106:00 am
BNA
- BDL
1 stop7h 24m
United Airlines
Deal found 2/7![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 2/9. 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.
Sat 7/182:20 pm
BDL
- BNA
1 stop5h 21m
Delta
Sat 7/254:25 pm
BNA
- BDL
1 stop4h 42m
Delta
Deal found 2/9![Delta logo]()
$197
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:25 pm
ALB
- BNA
1 stop5h 14m
American Airlines
Fri 4/176:08 am
BNA
- ALB
1 stop4h 26m
American Airlines
Deal found 2/10![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 4/238:08 pm
BDL
- CVG
1 stop15h 47m
Frontier
Sun 4/265:20 pm
CVG
- BDL
2 stops18h 55m
Frontier
Deal found 2/9![Frontier logo]()
$277
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/314:54 pm
BDL
- BNA
1 stop5h 16m
Delta
Thu 4/26:00 am
BNA
- BDL
1 stop5h 04m
Delta
Deal found 2/9![Delta logo]()
$197
Last-minute flights from Massachusetts to KentuckyDiscover last-minute flight deals from Massachusetts to Kentucky. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Kentucky. Data last updated February 11, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/269:28 am
BOS
- TYS
Nonstop2h 41m
Allegiant Air
Sun 3/16:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$148
This JetBlue deal was found by Cheapflights users on 2/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Mon 3/26:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Deal found 2/8![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 2/8. 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 3/28:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Wed 3/46:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Deal found 2/8![JetBlue logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mon 3/26:10 pm
BOS
- BNA
1 stop14h 15m
Spirit Airlines
Mon 3/98:52 pm
BNA
- BOS
1 stop25h 52m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Tue 3/36:10 pm
BOS
- BNA
1 stop14h 15m
Spirit Airlines
Mon 3/98:52 pm
BNA
- BOS
1 stop25h 52m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Tue 3/39:08 am
BOS
- BNA
Nonstop3h 05m
JetBlue
Mon 3/166:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Deal found 2/8![JetBlue logo]()
$161
This Booking.com deal was found by Cheapflights users on 2/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/59:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Sun 3/86:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$135
This Southwest deal was found by Cheapflights users on 2/8. 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.
Sat 3/72:25 pm
BOS
- BNA
Nonstop2h 50m
Southwest
Mon 3/99:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Deal found 2/8![Southwest logo]()
$157
This Super.com deal was found by Cheapflights users on 2/9. 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.
Sun 3/88:03 pm
BOS
- BNA
Nonstop2h 59m
JetBlue
Wed 3/116:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Deal found 2/9![JetBlue logo]()
$165
This Super.com deal was found by Cheapflights users on 2/8. 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 3/98:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Mon 3/168:25 pm
BNA
- BOS
Nonstop2h 31m
JetBlue
Deal found 2/8![JetBlue logo]()
$160
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:27 am
BOS
- BNA
1 stop15h 21m
Spirit Airlines
Wed 3/118:30 am
BNA
- BOS
1 stop7h 45m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$156
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:27 am
BOS
- BNA
1 stop15h 21m
Spirit Airlines
Wed 3/182:27 pm
BNA
- BOS
1 stop8h 32m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$154
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 February 11, 2026.
Search for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 4/210:36 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/10![Allegiant Air logo]()
$75
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:27 am
BOS
- BNA
1 stop15h 21m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$76
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:49 pm
BOS
- BNA
1 stop6h 49m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$77
This Cheapflightsfares deal was found by Cheapflights users on 2/7. 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.
Tue 3/39:08 am
BOS
- BNA
Nonstop3h 05m
JetBlue
Deal found 2/7![JetBlue logo]()
$78
This Delta deal was found by Cheapflights users on 2/9. 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.
Tue 3/107:15 pm
BOS
- BNA
Nonstop3h 05m
Delta
Deal found 2/9![Delta logo]()
$79
This Trip.com deal was found by Cheapflights users on 2/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/98:08 pm
BDL
- BNA
1 stop15h 33m
Frontier
Deal found 2/10![Frontier logo]()
$79
This Super.com deal was found by Cheapflights users on 2/8. 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.
Tue 3/2412:36 pm
BOS
- CVG
1 stop5h 57m
Frontier
Deal found 2/8![Frontier logo]()
$79
This Priceline deal was found by Cheapflights users on 2/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/211:16 am
BOS
- BNA
1 stop7h 06m
Frontier
Deal found 2/7![Frontier logo]()
$80
This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1012:36 pm
BOS
- CVG
1 stop5h 57m
Frontier
Deal found 2/10![Frontier logo]()
$80
This Mytrip deal was found by Cheapflights users on 2/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:10 pm
BOS
- BNA
1 stop14h 15m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 4/145:45 am
BOS
- BNA
1 stop8h 44m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Tue 4/288:45 pm
BOS
- BNA
Nonstop2h 49m
JetBlue
Deal found 2/8![JetBlue 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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $122 (Kiwi.com) |
One-way from | $75 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $405 |
Good round-trip deal | $347 or less |
Good one-way deal | $268 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 2,558,603 searches. Data last updated February 11, 2026.
Use the filters below to find and compare flights from Massachusetts to Kentucky that are best for you.
Fly from
Massachusetts
Fly to
Kentucky
Route
Depart
Return
Price
BostonKnoxville
BOS - TYS
BOSTYS
Boston Logan Intl
Thu 4/2
10:36 am-1:05 pm
Nonstop2h 29m
Knoxville McGhee Tyson
Sun 4/5
7:30 am-9:46 am
Nonstop2h 16m
$138
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Sat 2/28
8:07 am-10:20 am
Nonstop3h 13m
Nashville Intl
Tue 3/3
5:45 pm-9:16 pm
Nonstop2h 31m
$157
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Tue 3/10
8:20 am-10:15 am
Nonstop2h 55m
Nashville Intl
Tue 3/17
7:35 pm-11:00 pm
Nonstop2h 25m
$162
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Sat 3/7
5:45 am-9:22 am
1 stop4h 37m
Nashville Intl
Thu 3/12
8:00 am-3:16 pm
1 stop6h 16m
$177
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Thu 2/26
8:07 am-10:20 am
Nonstop3h 13m
Nashville Intl
Sat 2/28
3:30 pm-7:04 pm
Nonstop2h 34m
$177
HartfordCincinnati
BDL - CVG
BDLCVG
Hartford Bradley Intl
Tue 2/24
9:49 am-9:25 pm
1 stop11h 36m
Cincinnati Cinci./N. Kentucky
Sat 2/28
11:15 am-8:20 pm
1 stop9h 05m
$181
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Sat 3/7
5:15 am-9:25 am
1 stop5h 10m
Nashville Intl
Mon 3/9
9:20 pm-12:45 am
Nonstop2h 25m
$187
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Tue 2/24
7:45 am-12:28 pm
1 stop5h 43m
Nashville Intl
Wed 3/4
7:30 am-5:21 pm
2 stops8h 51m
$187
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Wed 4/1
2:37 pm-6:56 pm
1 stop5h 19m
Nashville Intl
Wed 4/8
7:25 am-2:48 pm
1 stop6h 23m
$187
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Tue 3/17
8:55 pm-10:57 pm
Nonstop3h 02m
Nashville Intl
Fri 3/20
6:00 am-9:33 am
Nonstop2h 33m
$192
Showing 1-10 of 60 results
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.
BOS-TYS
BOS-BNA
BDL-BNA
BOS-CVG
BDL-SDF
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
BOS-TYS
BOS-BNA
BDL-BNA
BOS-CVG
What is the cheapest month to book a flight from Massachusetts to Kentucky?
Currently, September is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $196). Flying from Massachusetts to Kentucky in June is currently the most expensive (average of $299). 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 February 11, 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.
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 February 11, 2026.
See what other customers who have flown with Southwest, Delta, and United 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.
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 February 11, 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 2,558,603 searches. Data last updated February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$243 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$209 | Average$392 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$424 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$406 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$310 | Average$398 | FlexibilityNo cancel fee | On-time63% |