$39+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Jun 20 — Jun 271
Round-trip
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 May 21, 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 May 21, 2026.
This Super.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Tue 6/28:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17![Breeze Airways logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/49:40 am
BOS
- TYS
Nonstop2h 22m
Allegiant Air
Thu 7/97:30 am
TYS
- BOS
Nonstop2h 20m
Allegiant Air
Deal found 5/16![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/16![Allegiant Air logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 8/19:55 am
BOS
- TYS
Nonstop2h 22m
Allegiant Air
Sat 8/86:45 am
TYS
- BOS
Nonstop2h 20m
Allegiant Air
Deal found 5/16![Allegiant Air logo]()
$151
This Breeze Airways deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Sun 6/148:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/19![Breeze Airways logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:53 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Sat 6/136:45 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 5/18![Allegiant Air logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:53 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Sat 6/206:30 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$157
This Super.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/247:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Sun 5/318:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/16![Breeze Airways logo]()
$157
This Mytrip deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:39 pm
BOS
- TYS
Nonstop2h 28m
Allegiant Air
Sun 8/239:30 am
TYS
- BOS
Nonstop2h 19m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$159
This Flightnetwork deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:40 am
BOS
- TYS
Nonstop2h 22m
Allegiant Air
Sun 7/57:30 am
TYS
- BOS
Nonstop2h 20m
Allegiant Air
Deal found 5/18![Allegiant Air logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Thu 6/48:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17![Breeze Airways logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/16![Allegiant Air logo]()
$163
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 May 21, 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 May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:10 am
BOS
- BNA
1 stop5h 20m
Southwest
Sat 6/1312:50 pm
BNA
- BOS
Nonstop2h 30m
Southwest
Deal found 5/17![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
ALB
- BNA
1 stop5h 09m
Delta
Sun 8/26:05 am
BNA
- ALB
1 stop4h 40m
Delta
Deal found 5/17![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/33:02 pm
BDL
- BNA
1 stop4h 45m
United Airlines
Tue 7/76:00 am
BNA
- BDL
2 stops7h 06m
United Airlines
Deal found 5/16![United Airlines logo]()
$260
This JetBlue deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:00 am
BOS
- BNA
Nonstop2h 50m
JetBlue
Sat 6/275:48 pm
BNA
- BOS
1 stop5h 22m
JetBlue
Deal found 5/18![JetBlue logo]()
$300
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/211:55 am
BOS
- CVG
Nonstop2h 35m
American Airlines
Tue 7/77:10 am
CVG
- BOS
Nonstop2h 15m
American Airlines
Deal found 5/20![American Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:10 am
BDL
- TYS
1 stop12h 11m
Multiple Airlines
Thu 6/43:42 pm
TYS
- BDL
1 stop25h 03m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
ALB
- BNA
1 stop6h 30m
Delta
Sat 8/15:40 pm
BNA
- ALB
1 stop4h 41m
Delta
Deal found 5/18![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 pm
ALB
- BNA
1 stop5h 05m
Southwest
Tue 8/2511:15 am
BNA
- ALB
1 stop5h 15m
Southwest
Deal found 5/20![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/84:15 pm
ALB
- BNA
1 stop5h 25m
Southwest
Tue 7/146:50 am
BNA
- ALB
1 stop4h 25m
Southwest
Deal found 5/17![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 7/285:45 am
ALB
- BNA
1 stop7h 15m
Delta
Sun 8/25:10 am
BNA
- ALB
1 stop5h 15m
Delta
Deal found 5/16![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:00 am
ALB
- BNA
2 stops7h 18m
United Airlines
Tue 6/236:30 pm
BNA
- ALB
1 stop4h 17m
United Airlines
Deal found 5/19![United Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:15 am
ALB
- BNA
1 stop5h 45m
Southwest
Sun 8/25:15 am
BNA
- ALB
1 stop6h 10m
Southwest
Deal found 5/20![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:05 pm
BDL
- BNA
2 stops5h 50m
Southwest
Tue 8/188:50 am
BNA
- BDL
1 stop5h 00m
Southwest
Deal found 5/20![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:03 pm
BDL
- BNA
1 stop5h 32m
Delta
Sun 7/264:31 pm
BNA
- BDL
1 stop5h 25m
Delta
Deal found 5/17![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
BDL
- BNA
1 stop4h 29m
United Airlines
Tue 7/149:53 am
BNA
- BDL
2 stops13h 06m
United Airlines
Deal found 5/17![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:15 pm
ALB
- BNA
2 stops6h 25m
Southwest
Mon 9/145:25 am
BNA
- ALB
1 stop6h 15m
Southwest
Deal found 5/20![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:20 am
BOS
- BNA
Nonstop2h 56m
Delta
Mon 7/135:35 pm
BNA
- BOS
Nonstop2h 44m
Delta
Deal found 5/17![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
BDL
- BNA
1 stop4h 29m
United Airlines
Sat 8/19:57 am
BNA
- BDL
2 stops13h 02m
United Airlines
Deal found 5/20![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/195:25 pm
BDL
- TYS
1 stop4h 33m
American Airlines
Fri 6/267:59 pm
TYS
- BDL
1 stop4h 56m
American Airlines
Deal found 5/20![American Airlines logo]()
$393
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:00 pm
BDL
- BNA
1 stop5h 40m
Southwest
Tue 7/2112:00 pm
BNA
- BDL
Nonstop2h 20m
Southwest
Deal found 5/17![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
BDL
- BNA
2 stops7h 29m
United Airlines
Wed 6/1712:49 pm
BNA
- BDL
2 stops10h 10m
United Airlines
Deal found 5/17![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:00 pm
BOS
- TYS
1 stop4h 53m
Delta
Wed 7/87:43 pm
TYS
- BOS
1 stop5h 37m
Delta
Deal found 5/20![Delta logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:16 am
BDL
- LEX
1 stop4h 11m
American Airlines
Sun 9/204:10 pm
LEX
- BDL
1 stop7h 00m
American Airlines
Deal found 5/21![American Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:45 am
BOS
- BNA
2 stops7h 33m
United Airlines
Wed 7/156:00 am
BNA
- BOS
1 stop5h 57m
United Airlines
Deal found 5/20![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:00 pm
BOS
- TYS
1 stop5h 15m
Delta
Tue 7/711:00 am
TYS
- BOS
1 stop7h 40m
Delta
Deal found 5/20![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:40 pm
ALB
- BNA
1 stop5h 25m
Southwest
Thu 9/175:40 am
BNA
- ALB
1 stop4h 30m
Southwest
Deal found 5/19![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:30 am
BOS
- LEX
1 stop4h 50m
Delta
Mon 10/127:45 pm
LEX
- BOS
1 stop5h 13m
Delta
Deal found 5/19![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:40 am
BDL
- BNA
2 stops8h 15m
Southwest
Tue 7/281:30 pm
BNA
- BDL
2 stops7h 15m
Southwest
Deal found 5/20![Southwest logo]()
$287
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:58 pm
BDL
- TYS
1 stop8h 02m
United Airlines
Tue 10/272:00 pm
TYS
- BDL
1 stop7h 22m
United Airlines
Deal found 5/20![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/67:00 am
BOS
- LEX
1 stop7h 26m
Delta
Sat 6/135:56 pm
LEX
- BOS
1 stop7h 35m
Delta
Deal found 5/16![Delta logo]()
$309
Last-minute flights from Massachusetts to KentuckyDiscover last-minute flight deals from Massachusetts to Kentucky. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Kentucky. Data last updated May 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/16![Allegiant Air logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/16![Allegiant Air logo]()
$150
This Super.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 5/247:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Sun 5/318:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/16![Breeze Airways logo]()
$157
This Super.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Tue 6/28:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17![Breeze Airways logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Thu 6/48:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17![Breeze Airways logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Sun 5/318:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/17![Breeze Airways logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:21 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Mon 6/85:15 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:53 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Sat 6/136:45 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 5/18![Allegiant Air logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:53 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Sat 6/206:30 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$157
This Breeze Airways deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Sun 6/148:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 5/19![Breeze Airways logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Mon 6/155:20 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Fri 6/192:10 pm
BNA
- ALB
1 stop18h 38m
Allegiant Air
Deal found 5/19![Allegiant Air logo]()
$169
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 May 21, 2026.
Search for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:10 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$39
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/159:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/19![Allegiant Air logo]()
$43
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/19![Allegiant Air logo]()
$48
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:22 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:22 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/18![Allegiant Air logo]()
$57
This Trip.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/299:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/89:13 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 5/16![Allegiant Air logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 5/19![Breeze Airways logo]()
$63
This Super.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 5/20![Breeze Airways logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:38 pm
ALB
- BNA
Nonstop2h 21m
Allegiant Air
Deal found 5/20![Allegiant Air logo]()
$69
This Super.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 5/20![Breeze Airways logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:53 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$74
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 May 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $149 (Kiwi.com) |
One-way from | $39 (Kiwi.com) |
Popular in | April |
Cheapest in | August |
Average price | $470 |
Good round-trip deal | $446 or less |
Good one-way deal | $273 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 May 21, 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
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Sat 6/6
5:10 am-9:30 am
1 stop5h 20m
Nashville Intl
Sat 6/13
12:50 pm-4:20 pm
Nonstop2h 30m
$237
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Wed 7/29
6:00 am-10:09 am
1 stop5h 09m
Nashville Intl
Sun 8/2
6:05 am-11:45 am
1 stop4h 40m
$241
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Wed 7/29
6:00 am-11:30 am
1 stop6h 30m
Nashville Intl
Sat 8/1
5:40 pm-11:21 pm
1 stop4h 41m
$241
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Thu 8/20
6:05 pm-10:10 pm
1 stop5h 05m
Nashville Intl
Tue 8/25
11:15 am-5:30 pm
1 stop5h 15m
$241
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Wed 7/8
4:15 pm-8:40 pm
1 stop5h 25m
Nashville Intl
Tue 7/14
6:50 am-12:15 pm
1 stop4h 25m
$241
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Tue 7/28
5:45 am-12:00 pm
1 stop7h 15m
Nashville Intl
Sun 8/2
5:10 am-11:25 am
1 stop5h 15m
$241
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Wed 7/29
9:15 am-2:00 pm
1 stop5h 45m
Nashville Intl
Sun 8/2
5:15 am-12:25 pm
1 stop6h 10m
$241
HartfordNashville
BDL - BNA
BDLBNA
Hartford Bradley Intl
Wed 8/12
3:05 pm-7:55 pm
2 stops5h 50m
Nashville Intl
Tue 8/18
8:50 am-2:50 pm
1 stop5h 00m
$242
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Fri 9/11
1:15 pm-6:40 pm
2 stops6h 25m
Nashville Intl
Mon 9/14
5:25 am-12:40 pm
1 stop6h 15m
$246
HartfordNashville
BDL - BNA
BDLBNA
Hartford Bradley Intl
Fri 7/3
3:02 pm-6:47 pm
1 stop4h 45m
Nashville Intl
Tue 7/7
6:00 am-2:06 pm
2 stops7h 06m
$260
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.
BDL-CVG
BOS-TYS
ALB-BNA
BDL-BNA
BDL-TYS
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
BDL-CVG
BOS-TYS
ALB-BNA
BDL-BNA
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 $98). Flying from Massachusetts to Kentucky in March is currently the most expensive (average of $275). 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 May 21, 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?
How far ahead should I book a flight from Massachusetts to Kentucky?
The best time to book flights from Massachusetts to Kentucky is 34 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 May 21, 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.
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
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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 May 21, 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 4 airlines flying from Massachusetts to Kentucky
Discover the top 4 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 May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$508 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$397 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$403 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$335 | Average$479 | FlexibilityNo cancel fee | On-time63% |