$50+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Mar 27 — Apr 31
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 25, 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 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/96:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 4/269:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/22![Allegiant Air logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 5/295:25 pm
BNA
- ALB
Nonstop2h 06m
Allegiant Air
Mon 6/19:21 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 2/22![Allegiant Air logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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
Sun 3/2910:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/25![Allegiant Air logo]()
$125
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 5/57:03 am
BNA
- BOS
1 stop7h 25m
Delta
Wed 5/132:50 pm
BOS
- BNA
Nonstop2h 53m
Delta
Deal found 2/24![Delta logo]()
$129
This JetBlue deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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.
Thu 5/76:00 am
BNA
- BOS
Nonstop2h 29m
JetBlue
Mon 5/114:00 pm
BOS
- BNA
Nonstop2h 55m
JetBlue
Deal found 2/25![JetBlue logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 2/25![Allegiant Air logo]()
$134
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/226:05 am
BNA
- BOS
Nonstop2h 46m
Delta
Sat 4/255:30 am
BOS
- BNA
1 stop4h 38m
Delta
Deal found 2/23![Delta logo]()
$135
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 2/23![Delta logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/96:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 4/129:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/23![Allegiant Air logo]()
$139
This JetBlue deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 5/26:00 am
BNA
- BOS
Nonstop2h 29m
JetBlue
Sun 5/39:45 am
BOS
- BNA
Nonstop2h 51m
JetBlue
Deal found 2/24![JetBlue logo]()
$144
This Super.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/18:40 pm
BNA
- BOS
Nonstop2h 33m
JetBlue
Wed 4/87:35 am
BOS
- BNA
Nonstop2h 57m
JetBlue
Deal found 2/24![JetBlue logo]()
$146
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/85:30 am
BNA
- BOS
1 stop7h 10m
Southwest
Tue 4/148:10 am
BOS
- BNA
Nonstop2h 45m
Southwest
Deal found 2/25![Southwest logo]()
$147
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 25, 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 25, 2026.
This JetBlue deal was found by Cheapflights users on 2/21. 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 JetBlue 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 2/21![JetBlue logo]()
$158
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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
Sun 5/37:55 am
BOS
- BNA
Nonstop2h 57m
Delta
Deal found 2/24![Delta logo]()
$170
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/227:42 am
BNA
- BOS
1 stop4h 47m
United Airlines
Sat 4/255:45 am
BOS
- BNA
1 stop4h 42m
United Airlines
Deal found 2/22![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/2211:55 am
BNA
- BOS
1 stop5h 40m
Southwest
Sat 4/256:00 pm
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 2/22![Southwest logo]()
$177
This American Airlines deal was found by Cheapflights users on 2/21. 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.
Wed 3/116:40 am
LEX
- BOS
1 stop4h 48m
American Airlines
Sat 3/147:40 am
BOS
- LEX
1 stop6h 53m
American Airlines
Deal found 2/21![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:43 pm
CVG
- BDL
2 stops23h 30m
Frontier
Mon 4/69:53 pm
BDL
- CVG
1 stop13h 32m
Frontier
Deal found 2/21![Frontier logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2010:42 am
SDF
- BOS
2 stops13h 33m
Multiple Airlines
Tue 8/2510:12 am
BOS
- SDF
1 stop22h 24m
Multiple Airlines
Deal found 2/25![Multiple Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/279:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Mon 3/3010:30 am
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 2/23![Southwest logo]()
$192
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/16:00 am
BNA
- BDL
2 stops7h 08m
United Airlines
Sun 4/56:00 am
BDL
- BNA
2 stops7h 28m
United Airlines
Deal found 2/22![United Airlines logo]()
$221
This Southwest deal was found by Cheapflights users on 2/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Wed 3/112:00 pm
BOS
- BNA
1 stop6h 00m
Southwest
Deal found 2/21![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/62:32 pm
BNA
- BDL
1 stop5h 50m
Delta
Mon 4/137:01 pm
BDL
- BNA
1 stop5h 23m
Delta
Deal found 2/23![Delta logo]()
$238
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 5/97:35 am
BNA
- BDL
2 stops10h 22m
United Airlines
Sun 5/176:05 am
BDL
- BNA
1 stop4h 11m
United Airlines
Deal found 2/22![United Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:38 pm
BNA
- ALB
1 stop4h 28m
Delta
Fri 8/76:00 am
ALB
- BNA
1 stop6h 07m
Delta
Deal found 2/24![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:39 pm
BNA
- BOS
1 stop5h 20m
United Airlines
Sun 5/107:30 am
BOS
- BNA
1 stop5h 56m
United Airlines
Deal found 2/21![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 2/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:05 pm
BNA
- BOS
1 stop8h 15m
Southwest
Mon 5/42:30 pm
BOS
- BNA
2 stops7h 00m
Southwest
Deal found 2/21![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 7/163:44 pm
LEX
- BOS
1 stop6h 43m
Delta
Tue 7/215:30 am
BOS
- LEX
1 stop4h 46m
Delta
Deal found 2/23![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/58:40 am
BNA
- BOS
1 stop6h 36m
United Airlines
Tue 5/125:45 am
BOS
- BNA
2 stops7h 41m
United Airlines
Deal found 2/25![United Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 4/283:30 pm
SDF
- BOS
2 stops6h 50m
Southwest
Tue 5/57:20 am
BOS
- SDF
2 stops7h 25m
Southwest
Deal found 2/25![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/78:20 pm
LEX
- BOS
1 stop5h 08m
Delta
Sun 5/105:40 am
BOS
- LEX
1 stop4h 22m
Delta
Deal found 2/21![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/17:00 am
TYS
- BDL
1 stop7h 15m
United Airlines
Sun 4/56:00 am
BDL
- TYS
1 stop4h 50m
United Airlines
Deal found 2/22![United Airlines logo]()
$250
This Southwest deal was found by Cheapflights users on 2/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:10 am
TYS
- BOS
1 stop5h 35m
Southwest
Tue 7/72:25 pm
BOS
- TYS
1 stop6h 50m
Southwest
Deal found 2/21![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/138:20 pm
LEX
- BOS
1 stop5h 08m
Delta
Wed 6/105:30 am
BOS
- LEX
1 stop4h 46m
Delta
Deal found 2/25![Delta logo]()
$284
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:39 pm
BNA
- ALB
1 stop4h 54m
United Airlines
Sun 5/36:00 am
ALB
- BNA
1 stop4h 16m
United Airlines
Deal found 2/23![United Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/87:05 am
TYS
- BDL
2 stops7h 35m
Southwest
Mon 4/1311:40 am
BDL
- TYS
2 stops8h 40m
Southwest
Deal found 2/24![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/215:54 pm
TYS
- BOS
1 stop7h 21m
Delta
Thu 4/232:00 pm
BOS
- TYS
1 stop6h 35m
Delta
Deal found 2/24![Delta logo]()
$287
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 5/111:45 am
BNA
- BDL
2 stops10h 59m
United Airlines
Sun 5/36:05 am
BDL
- BNA
2 stops7h 21m
United Airlines
Deal found 2/24![United Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/141:57 pm
TYS
- BDL
1 stop4h 13m
Delta
Sun 5/176:00 am
BDL
- TYS
1 stop7h 10m
Delta
Deal found 2/23![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/236:34 pm
BNA
- BDL
1 stop4h 25m
United Airlines
Mon 3/305:05 pm
BDL
- BNA
1 stop5h 54m
United Airlines
Deal found 2/25![United Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/157:55 pm
LEX
- BOS
1 stop5h 18m
Delta
Mon 3/234:00 pm
BOS
- LEX
1 stop7h 06m
Delta
Deal found 2/25![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/212:50 pm
CVG
- BOS
2 stops8h 35m
Southwest
Tue 5/56:20 am
BOS
- CVG
2 stops8h 40m
Southwest
Deal found 2/25![Southwest logo]()
$339
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated February 25, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated February 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/77:46 pm
CVG
- BDL
1 stop15h 26m
Frontier
Sun 3/158:08 pm
BDL
- CVG
1 stop11h 15m
Frontier
Deal found 2/22![Frontier logo]()
$169
This Cheapflightsfares deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/127:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Thu 3/199:00 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/24![Allegiant Air logo]()
$151
This Super.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 3/126:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Wed 3/188:55 pm
BOS
- BNA
Nonstop3h 02m
JetBlue
Deal found 2/25![JetBlue logo]()
$174
This Cheapflightsfares deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/157:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/229:00 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/23![Allegiant Air logo]()
$159
This Priceline deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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.
Wed 3/188:50 am
BNA
- BOS
1 stop7h 18m
JetBlue
Wed 3/188:55 pm
BOS
- BNA
Nonstop3h 02m
JetBlue
Deal found 2/22![JetBlue logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/226:00 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/2910:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/22![Allegiant Air logo]()
$157
This CheapOair deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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.
Tue 3/242:27 pm
BNA
- BOS
1 stop24h 01m
Spirit Airlines
Tue 3/316:01 am
BOS
- BNA
1 stop18h 37m
Spirit Airlines
Deal found 2/23![Spirit Airlines logo]()
$178
This JetBlue deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/256:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Sat 3/288:55 pm
BOS
- BNA
Nonstop3h 02m
JetBlue
Deal found 2/23![JetBlue logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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
Sun 3/2910:30 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 2/25![Allegiant Air logo]()
$125
This Super.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Sun 4/56:25 am
BOS
- BNA
Nonstop2h 50m
JetBlue
Deal found 2/24![JetBlue logo]()
$165
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/309:30 pm
BNA
- BOS
1 stop9h 35m
Southwest
Sat 4/48:00 am
BOS
- BNA
Nonstop3h 00m
Southwest
Deal found 2/24![Southwest logo]()
$183
This Super.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/318:40 pm
BNA
- BOS
Nonstop2h 33m
JetBlue
Tue 4/77:35 am
BOS
- BNA
Nonstop2h 57m
JetBlue
Deal found 2/22![JetBlue logo]()
$179
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 25, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 2/24![Allegiant Air logo]()
$50
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” 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 5/225:25 pm
BNA
- ALB
Nonstop2h 06m
Allegiant Air
Deal found 2/25![Allegiant Air logo]()
$52
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/196:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 2/24![Allegiant Air logo]()
$63
This Booking.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 6/49:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 2/24![Breeze Airways logo]()
$64
This Booking.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 6/119:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 2/22![Breeze Airways logo]()
$74
This Southwest deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/158:15 am
TYS
- BDL
1 stop6h 25m
Southwest
Deal found 2/24![Southwest logo]()
$78
This Frontier deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:46 pm
CVG
- BOS
1 stop5h 45m
Frontier
Deal found 2/24![Frontier logo]()
$80
This Cheapflightsfares deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/317:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/23![Allegiant Air logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 3/2412:34 pm
CVG
- BOS
1 stop26h 54m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$84
This Booking.com deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 5/219:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 2/22![Breeze Airways logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/247:43 pm
CVG
- BOS
1 stop15h 30m
Frontier
Deal found 2/23![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/107:43 pm
CVG
- BOS
1 stop14h 46m
Frontier
Deal found 2/23![Frontier logo]()
$87
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 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $92 (Cheapflightsfares) |
One-way from | $50 (Kiwi.com) |
Popular in | February |
Cheapest in | September |
Average price | $419 |
Good round-trip deal | $452 or less |
Good one-way deal | $268 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 25, 2026.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 4/3
8:00 pm-11:33 pm
Nonstop2h 33m
Boston Logan Intl
Sun 4/5
6:25 am-8:15 am
Nonstop2h 50m
$158
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 5/1
6:40 pm-10:15 pm
Nonstop2h 35m
Boston Logan Intl
Sun 5/3
7:55 am-9:52 am
Nonstop2h 57m
$170
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 4/22
7:42 am-1:29 pm
1 stop4h 47m
Boston Logan Intl
Sat 4/25
5:45 am-9:27 am
1 stop4h 42m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 4/22
11:55 am-6:35 pm
1 stop5h 40m
Boston Logan Intl
Sat 4/25
6:00 pm-7:55 pm
Nonstop2h 55m
$177
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 3/27
9:20 pm-12:45 am
Nonstop2h 25m
Boston Logan Intl
Mon 3/30
10:30 am-12:25 pm
Nonstop2h 55m
$192
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Mon 3/9
9:20 pm-12:45 am
Nonstop2h 25m
Boston Logan Intl
Wed 3/11
2:00 pm-7:00 pm
1 stop6h 00m
$202
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Wed 4/1
6:00 am-2:08 pm
2 stops7h 08m
Hartford Bradley Intl
Sun 4/5
6:00 am-12:28 pm
2 stops7h 28m
$221
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Mon 4/6
2:32 pm-9:22 pm
1 stop5h 50m
Hartford Bradley Intl
Mon 4/13
7:01 pm-11:24 pm
1 stop5h 23m
$238
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Sat 5/9
7:35 am-6:57 pm
2 stops10h 22m
Hartford Bradley Intl
Sun 5/17
6:05 am-9:16 am
1 stop4h 11m
$242
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 5/8
6:39 pm-12:59 am
1 stop5h 20m
Boston Logan Intl
Sun 5/10
7:30 am-12:26 pm
1 stop5h 56m
$247
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Kentucky with our price prediction graph.
TYS-BOS
BNA-BOS
CVG-BDL
BNA-ALB
TYS-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Massachusetts
USKY-USMA
TYS-BOS
BNA-BOS
CVG-BDL
BNA-ALB
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 25, 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 25, 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.
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Overall
8.0
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 25, 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$336 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | 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$406 | FlexibilityNo cancel fee | On-time69% |