$54+ 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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Mar 21 — Mar 281
1 adult, Economy
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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 February 19, 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 February 19, 2026.
This Mytrip deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 2/266:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Sun 3/19:28 am
BOS
- TYS
Nonstop2h 41m
Allegiant Air
Deal found 2/15![Allegiant Air logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/89:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$120
This Mytrip deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Thu 3/59:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 6/29:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Sun 6/77:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/19![Breeze Airways logo]()
$127
This flygcity.se deal was found by Cheapflights users on 2/18. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/38:00 pm
BNA
- BOS
Nonstop2h 33m
JetBlue
Sun 4/56:25 am
BOS
- BNA
Nonstop2h 50m
JetBlue
Deal found 2/18![JetBlue logo]()
$134
This Cheapflightsfares deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/19![Allegiant Air logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 2/17. 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.
Thu 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/229:00 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/17![Allegiant Air logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 2/17. 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.
Sun 6/77:30 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Thu 6/1110:38 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Deal found 2/17![Allegiant Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/236:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/15![Allegiant Air logo]()
$155
This Super.com deal was found by Cheapflights users on 2/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
BNA
- BOS
Nonstop2h 29m
JetBlue
Sat 5/28:45 pm
BOS
- BNA
Nonstop2h 49m
JetBlue
Deal found 2/18![JetBlue logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:00 pm
BNA
- BOS
Nonstop2h 33m
JetBlue
Tue 4/149:45 am
BOS
- BNA
Nonstop2h 51m
JetBlue
Deal found 2/18![JetBlue logo]()
$156
This Breeze Airways deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 6/119:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Sun 6/147:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/15![Breeze Airways logo]()
$158
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 February 19, 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 February 19, 2026.
This United Airlines deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 4/211:25 pm
BNA
- BOS
1 stop4h 41m
United Airlines
Sat 4/256:19 pm
BOS
- BNA
1 stop5h 50m
United Airlines
Deal found 2/15![United Airlines logo]()
$177
This JetBlue deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:00 am
BNA
- BOS
Nonstop2h 29m
JetBlue
Tue 5/269:25 am
BOS
- BNA
1 stop8h 28m
JetBlue
Deal found 2/17![JetBlue logo]()
$177
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/16:40 pm
BNA
- BOS
Nonstop2h 35m
Delta
Mon 5/43:40 pm
BOS
- BNA
Nonstop2h 55m
Delta
Deal found 2/15![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/59:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Tue 3/106:25 pm
BOS
- BNA
Nonstop3h 05m
Southwest
Deal found 2/15![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/129:03 pm
BNA
- BDL
1 stop14h 17m
Multiple Airlines
Mon 3/168:08 pm
BDL
- BNA
1 stop15h 33m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:25 am
BNA
- BDL
1 stop7h 26m
American Airlines
Sat 5/305:24 pm
BDL
- BNA
1 stop7h 24m
American Airlines
Deal found 2/19![American Airlines logo]()
$197
This Expedia deal was found by Cheapflights users on 2/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:20 pm
CVG
- BDL
1 stop25h 57m
Frontier
Sun 5/31:07 pm
BDL
- CVG
1 stop5h 29m
Frontier
Deal found 2/17![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 6/286:55 pm
SDF
- BDL
1 stop27h 53m
Breeze Airways
Fri 7/37:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 2/15![Breeze Airways logo]()
$271
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/169:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Mon 3/237:25 pm
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 2/18![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/18. 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.
Tue 3/177:05 am
BNA
- BOS
Nonstop2h 38m
Delta
Tue 3/177:15 pm
BOS
- BNA
Nonstop3h 05m
Delta
Deal found 2/18![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Wed 4/297:42 am
BNA
- BOS
1 stop5h 44m
United Airlines
Sat 5/27:30 am
BOS
- BNA
1 stop5h 56m
United Airlines
Deal found 2/16![United Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Thu 3/2611:36 am
BNA
- BDL
1 stop6h 37m
Multiple Airlines
Mon 4/69:53 pm
BDL
- BNA
1 stop22h 53m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$190
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/297:05 am
BNA
- BOS
Nonstop2h 43m
Delta
Tue 6/27:20 pm
BOS
- BNA
Nonstop2h 55m
Delta
Deal found 2/15![Delta logo]()
$177
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/115:00 am
BNA
- ALB
1 stop6h 07m
American Airlines
Wed 3/255:28 pm
ALB
- BNA
1 stop4h 55m
American Airlines
Deal found 2/16![American Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:00 am
BNA
- BOS
1 stop5h 20m
Southwest
Tue 3/176:25 pm
BOS
- BNA
Nonstop3h 05m
Southwest
Deal found 2/18![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/167:05 am
BNA
- BOS
Nonstop2h 43m
Delta
Sat 5/165:25 pm
BOS
- BNA
Nonstop3h 03m
Delta
Deal found 2/15![Delta logo]()
$177
This CheapOair deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:14 pm
CVG
- BDL
1 stop14h 09m
Frontier
Fri 3/68:08 pm
BDL
- CVG
1 stop11h 15m
Frontier
Deal found 2/15![Frontier logo]()
$216
This United Airlines deal was found by Cheapflights users on 2/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/182:49 pm
BNA
- ALB
1 stop5h 30m
United Airlines
Sat 4/256:05 am
ALB
- BNA
1 stop5h 22m
United Airlines
Deal found 2/18![United Airlines logo]()
$197
This American Airlines deal was found by Cheapflights users on 2/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/67:19 pm
BNA
- BDL
1 stop4h 09m
American Airlines
Mon 4/137:29 pm
BDL
- BNA
1 stop5h 25m
American Airlines
Deal found 2/17![American Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/39:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Sun 4/55:15 am
BOS
- BNA
1 stop5h 00m
Southwest
Deal found 2/18![Southwest logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/16:30 am
TYS
- BOS
Nonstop2h 08m
Multiple Airlines
Wed 3/46:10 pm
BOS
- TYS
1 stop29h 17m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$211
This United Airlines deal was found by Cheapflights users on 2/17. 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 3/276:34 pm
BNA
- BDL
1 stop4h 25m
United Airlines
Mon 3/305:05 pm
BDL
- BNA
1 stop5h 54m
United Airlines
Deal found 2/17![United Airlines logo]()
$197
This Priceline deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:45 am
CVG
- BDL
1 stop8h 28m
Frontier
Thu 3/198:08 pm
BDL
- CVG
1 stop11h 15m
Frontier
Deal found 2/18![Frontier logo]()
$230
This American Airlines deal was found by Cheapflights users on 2/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:00 am
BNA
- ALB
1 stop4h 07m
American Airlines
Tue 3/175:07 pm
ALB
- BNA
2 stops6h 29m
American Airlines
Deal found 2/16![American Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 2/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:45 am
BNA
- BOS
Nonstop2h 30m
Southwest
Tue 3/318:55 am
BOS
- BNA
2 stops9h 10m
Southwest
Deal found 2/16![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 2/16. 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.
Thu 4/165:25 am
BNA
- ALB
1 stop5h 48m
Delta
Sun 4/196:00 am
ALB
- BNA
1 stop4h 06m
Delta
Deal found 2/16![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 2/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:19 pm
BNA
- ALB
1 stop5h 11m
United Airlines
Tue 3/176:00 am
ALB
- BNA
1 stop7h 34m
United Airlines
Deal found 2/18![United Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Wed 3/41:19 pm
SDF
- BDL
1 stop27h 56m
Multiple Airlines
Sun 3/86:00 am
BDL
- SDF
1 stop7h 26m
Multiple Airlines
Deal found 2/17![Multiple Airlines logo]()
$227
This Expedia deal was found by Cheapflights users on 2/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:45 am
CVG
- BDL
1 stop14h 41m
Frontier
Sun 4/129:21 pm
BDL
- CVG
1 stop27h 37m
Frontier
Deal found 2/17![Frontier logo]()
$235
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 4/86:05 am
BNA
- ALB
1 stop6h 27m
Delta
Wed 4/156:00 am
ALB
- BNA
1 stop4h 06m
Delta
Deal found 2/15![Delta logo]()
$197
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated February 19, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated February 19, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 2/266:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Sun 3/19:28 am
BOS
- TYS
Nonstop2h 41m
Allegiant Air
Deal found 2/15![Allegiant Air logo]()
$112
This Mytrip deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Thu 3/59:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$125
This Super.com deal was found by Cheapflights users on 2/16. 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.
Wed 3/46:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Mon 3/98:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Deal found 2/16![JetBlue logo]()
$170
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Sat 3/78:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Deal found 2/18![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/89:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 2/17. 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.
Thu 3/56:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Thu 3/1210:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/17![Allegiant Air logo]()
$168
This Super.com deal was found by Cheapflights users on 2/17. 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 3/128:25 pm
BNA
- BOS
Nonstop2h 31m
JetBlue
Mon 3/169:35 pm
BOS
- BNA
Nonstop3h 01m
JetBlue
Deal found 2/17![JetBlue logo]()
$169
This Super.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/176:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Tue 3/247:10 am
BOS
- BNA
Nonstop3h 00m
JetBlue
Deal found 2/15![JetBlue logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 2/17. 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.
Thu 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/229:00 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/17![Allegiant Air logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Multiple Airlines
Tue 3/245:49 pm
BOS
- TYS
1 stop16h 51m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Multiple Airlines
Mon 3/235:49 pm
BOS
- TYS
1 stop20h 21m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$176
This Super.com deal was found by Cheapflights users on 2/16. 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.
Tue 3/246:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Tue 3/317:40 am
BOS
- BNA
Nonstop2h 52m
JetBlue
Deal found 2/16![JetBlue logo]()
$174
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 February 19, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 19, 2026.
This Booking.com deal was found by Cheapflights users on 2/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 2/18![Breeze Airways logo]()
$54
This Cheapflightsfares deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$56
This Super.com deal was found by Cheapflights users on 2/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:30 am
TYS
- BOS
Nonstop2h 08m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 4/1312:19 pm
CVG
- BOS
1 stop23h 46m
Frontier
Deal found 2/16![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Thu 5/77:43 pm
CVG
- BDL
1 stop16h 32m
Frontier
Deal found 2/18![Frontier logo]()
$71
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:43 pm
CVG
- BOS
1 stop5h 30m
Frontier
Deal found 2/18![Frontier logo]()
$80
This Priceline deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:23 am
BNA
- BDL
1 stop7h 54m
Frontier
Deal found 2/15![Frontier logo]()
$80
This Booking.com deal was found by Cheapflights users on 2/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1610:23 am
BNA
- BOS
1 stop22h 58m
Frontier
Deal found 2/17![Frontier logo]()
$86
This Super.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/312:03 pm
BNA
- BOS
Nonstop2h 33m
JetBlue
Deal found 2/15![JetBlue logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Fri 8/145:23 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 2/18![Allegiant Air logo]()
$87
This CheapOair deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/252:27 pm
BNA
- BOS
1 stop8h 32m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Fri 7/105:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 2/16![Allegiant Air logo]()
$88
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 February 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $112 (Mytrip) |
One-way from | $54 (Booking.com) |
Popular in | February |
Cheapest in | September |
Average price | $419 |
Good round-trip deal | $413 or less |
Good one-way deal | $294 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 February 19, 2026.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.
Fly from
Kentucky
Fly to
Massachusetts
Route
Depart
Return
Price
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Tue 4/21
1:25 pm-7:06 pm
1 stop4h 41m
Boston Logan Intl
Sat 4/25
6:19 pm-11:09 pm
1 stop5h 50m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 5/20
6:00 am-9:29 am
Nonstop2h 29m
Boston Logan Intl
Tue 5/26
9:25 am-4:53 pm
1 stop8h 28m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 5/1
6:40 pm-10:15 pm
Nonstop2h 35m
Boston Logan Intl
Mon 5/4
3:40 pm-5:35 pm
Nonstop2h 55m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Thu 3/5
9:20 pm-12:45 am
Nonstop2h 25m
Boston Logan Intl
Tue 3/10
6:25 pm-8:30 pm
Nonstop3h 05m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Mon 3/16
9:20 pm-12:45 am
Nonstop2h 25m
Boston Logan Intl
Mon 3/23
7:25 pm-9:20 pm
Nonstop2h 55m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Tue 3/17
7:05 am-10:43 am
Nonstop2h 38m
Boston Logan Intl
Tue 3/17
7:15 pm-9:20 pm
Nonstop3h 05m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 4/29
7:42 am-2:26 pm
1 stop5h 44m
Boston Logan Intl
Sat 5/2
7:30 am-12:26 pm
1 stop5h 56m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 5/29
7:05 am-10:48 am
Nonstop2h 43m
Boston Logan Intl
Tue 6/2
7:20 pm-9:15 pm
Nonstop2h 55m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Sat 5/16
7:05 am-10:48 am
Nonstop2h 43m
Boston Logan Intl
Sat 5/16
5:25 pm-7:28 pm
Nonstop3h 03m
$177
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Thu 3/12
9:03 pm-12:20 pm
1 stop14h 17m
Hartford Bradley Intl
Mon 3/16
8:08 pm-10:41 am
1 stop15h 33m
$187
Showing 1-10 of 60 results
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
CVG-BOS
BNA-BOS
BNA-ALB
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
CVG-BOS
BNA-BOS
What is the cheapest month to book a flight from Kentucky to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $139). Flying from Kentucky to Massachusetts in June 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 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 February 19, 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.
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 February 19, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United 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.
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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 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 February 19, 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 5 airlines flying from Kentucky to Massachusetts
Discover the top 5 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 February 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$339 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$216 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$209 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$382 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$438 | FlexibilityNo cancel fee | On-time69% |