$47+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
May 18 — May 251
Round-trip
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 April 18, 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 April 18, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/125:20 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Mon 6/159:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/13![Allegiant Air logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/196:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/13![Allegiant Air logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/225:25 pm
BNA
- ALB
Nonstop2h 06m
Allegiant Air
Fri 5/299:21 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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.
Fri 8/75:23 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Mon 8/109:22 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/76:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/46:30 am
TYS
- BOS
Nonstop2h 20m
Allegiant Air
Thu 7/1610:40 am
BOS
- TYS
Nonstop2h 22m
Allegiant Air
Deal found 4/14![Allegiant Air logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Mon 8/317:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 4/14![Breeze Airways logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 6/66:45 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Sun 6/1410:38 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 5/236:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/13![Allegiant Air logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/35:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Mon 7/69:10 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/14![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:23 am
SDF
- BDL
1 stop3h 28m
Breeze Airways
Mon 9/146:00 am
BDL
- SDF
1 stop3h 43m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$134
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 April 18, 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 April 18, 2026.
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/56:43 pm
BNA
- BDL
1 stop4h 50m
Delta
Mon 6/84:55 pm
BDL
- BNA
1 stop6h 29m
Delta
Deal found 4/13![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/246:30 pm
BNA
- BDL
1 stop4h 29m
United Airlines
Wed 7/86:09 am
BDL
- BNA
1 stop5h 25m
United Airlines
Deal found 4/13![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/306:05 pm
BNA
- ALB
1 stop4h 10m
Southwest
Thu 5/77:10 am
ALB
- BNA
1 stop5h 45m
Southwest
Deal found 4/13![Southwest logo]()
$241
This American Airlines deal was found by Cheapflights users on 4/17. 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.
Sat 5/162:45 pm
BNA
- ALB
1 stop6h 40m
American Airlines
Sat 5/237:32 pm
ALB
- BNA
1 stop5h 16m
American Airlines
Deal found 4/17![American Airlines logo]()
$241
This JetBlue deal was found by Cheapflights users on 4/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:05 am
BNA
- BOS
Nonstop2h 29m
JetBlue
Sat 5/27:45 pm
BOS
- BNA
Nonstop2h 52m
JetBlue
Deal found 4/15![JetBlue logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 7/16:00 am
BNA
- BDL
1 stop7h 24m
United Airlines
Wed 7/154:55 pm
BDL
- BNA
1 stop5h 50m
United Airlines
Deal found 4/13![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 4/16. 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 9/86:25 am
BNA
- ALB
1 stop4h 35m
Delta
Tue 9/155:30 am
ALB
- BNA
1 stop7h 27m
Delta
Deal found 4/16![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 6/232:45 pm
BNA
- BDL
1 stop5h 40m
Southwest
Tue 7/72:35 pm
BDL
- BNA
2 stops7h 15m
Southwest
Deal found 4/12![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/125:40 pm
BNA
- ALB
1 stop4h 29m
Delta
Sun 6/146:00 am
ALB
- BNA
1 stop4h 58m
Delta
Deal found 4/13![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/156:39 pm
BNA
- ALB
1 stop5h 09m
United Airlines
Sat 5/166:00 am
ALB
- BNA
1 stop5h 48m
United Airlines
Deal found 4/14![United Airlines logo]()
$241
This JetBlue deal was found by Cheapflights users on 4/17. 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 7/18:25 pm
BNA
- BOS
Nonstop2h 34m
JetBlue
Thu 7/95:33 pm
BOS
- BNA
Nonstop2h 57m
JetBlue
Deal found 4/17![JetBlue logo]()
$272
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 4/306:00 am
BNA
- BDL
1 stop7h 18m
United Airlines
Mon 5/45:05 pm
BDL
- BNA
1 stop5h 52m
United Airlines
Deal found 4/15![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/1212:50 pm
TYS
- BDL
2 stops9h 15m
Southwest
Tue 5/196:15 am
BDL
- TYS
2 stops10h 55m
Southwest
Deal found 4/14![Southwest logo]()
$271
This JetBlue deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:45 am
BNA
- BOS
1 stop8h 28m
JetBlue
Sat 5/910:19 am
BOS
- BNA
Nonstop2h 50m
JetBlue
Deal found 4/13![JetBlue logo]()
$280
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:00 pm
TYS
- ALB
1 stop5h 49m
Delta
Wed 10/141:59 pm
ALB
- TYS
1 stop6h 36m
Delta
Deal found 4/13![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Sat 6/67:00 am
BNA
- BOS
1 stop5h 32m
United Airlines
Tue 6/99:30 am
BOS
- BNA
1 stop5h 19m
United Airlines
Deal found 4/16![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/17:45 pm
BNA
- BOS
Nonstop2h 30m
Southwest
Mon 5/48:25 am
BOS
- BNA
Nonstop2h 45m
Southwest
Deal found 4/14![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 4/17. 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.
Tue 6/308:25 pm
BNA
- BOS
Nonstop2h 34m
JetBlue
Wed 7/812:42 pm
BOS
- BNA
1 stop5h 23m
JetBlue
Deal found 4/17![JetBlue logo]()
$290
This Delta deal was found by Cheapflights users on 4/15. 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.
Thu 7/166:00 am
BNA
- ALB
1 stop5h 47m
Delta
Tue 7/216:00 am
ALB
- BNA
1 stop4h 04m
Delta
Deal found 4/15![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 7/12:45 pm
BNA
- BDL
1 stop5h 40m
Southwest
Wed 7/155:55 am
BDL
- BNA
2 stops6h 05m
Southwest
Deal found 4/13![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/156:39 pm
BNA
- ALB
1 stop5h 09m
United Airlines
Sun 5/176:00 am
ALB
- BNA
1 stop5h 48m
United Airlines
Deal found 4/14![United Airlines logo]()
$266
This Delta deal was found by Cheapflights users on 4/15. 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 6/135:56 pm
LEX
- BOS
1 stop5h 18m
Delta
Tue 6/165:30 am
BOS
- LEX
1 stop4h 39m
Delta
Deal found 4/15![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 4/17. 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.
Tue 6/235:20 am
BNA
- BDL
1 stop4h 40m
Southwest
Fri 6/265:10 pm
BDL
- BNA
2 stops5h 40m
Southwest
Deal found 4/17![Southwest logo]()
$293
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/306:22 pm
BNA
- BOS
1 stop5h 46m
United Airlines
Fri 7/105:45 am
BOS
- BNA
1 stop4h 44m
United Airlines
Deal found 4/13![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 4/15. 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 6/35:52 pm
LEX
- BOS
1 stop5h 37m
Delta
Sat 6/67:00 am
BOS
- LEX
1 stop7h 26m
Delta
Deal found 4/15![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/221:05 pm
BNA
- ALB
1 stop6h 45m
Southwest
Sun 5/241:20 pm
ALB
- BNA
2 stops6h 25m
Southwest
Deal found 4/13![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/137:15 am
SDF
- BDL
2 stops6h 53m
United Airlines
Wed 5/205:05 pm
BDL
- SDF
1 stop5h 25m
United Airlines
Deal found 4/13![United Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/207:50 am
SDF
- BDL
1 stop4h 17m
Delta
Sat 5/236:27 pm
BDL
- SDF
1 stop5h 32m
Delta
Deal found 4/14![Delta logo]()
$278
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/76:35 am
TYS
- ALB
1 stop7h 40m
Southwest
Wed 5/139:10 am
ALB
- TYS
2 stops8h 00m
Southwest
Deal found 4/13![Southwest logo]()
$296
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 8/117:00 am
LEX
- BOS
2 stops7h 45m
United Airlines
Sat 9/125:01 pm
BOS
- LEX
1 stop5h 29m
United Airlines
Deal found 4/12![United Airlines logo]()
$280
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated April 18, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/13![Allegiant Air logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 4/196:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/13![Allegiant Air logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 4/306:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Thu 5/79:36 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/12![Allegiant Air logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/76:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Thu 5/79:40 pm
TYS
- BOS
1 stop26h 14m
Multiple Airlines
Sun 5/109:36 am
BOS
- TYS
Nonstop2h 29m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/91:05 pm
BNA
- BOS
1 stop19h 07m
Multiple Airlines
Wed 5/2010:07 am
BOS
- BNA
1 stop7h 10m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/95:02 pm
BNA
- BOS
1 stop15h 10m
Multiple Airlines
Tue 5/1910:07 am
BOS
- BNA
1 stop26h 53m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Tue 5/126:00 am
BNA
- BOS
1 stop16h 54m
Multiple Airlines
Tue 5/1910:07 am
BOS
- BNA
1 stop26h 53m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/135:02 pm
BNA
- BOS
1 stop15h 10m
Multiple Airlines
Wed 5/209:20 am
BOS
- BNA
1 stop7h 57m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/225:25 pm
BNA
- ALB
Nonstop2h 06m
Allegiant Air
Fri 5/299:21 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 4/16. 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 5/236:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Fri 5/295:25 pm
BNA
- ALB
Nonstop2h 06m
Multiple Airlines
Mon 6/17:53 pm
ALB
- BNA
1 stop28h 21m
Multiple Airlines
Deal found 4/15![Multiple Airlines 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 April 18, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 7/35:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 4/14![Allegiant Air logo]()
$47
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 6/195:15 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Deal found 4/14![Allegiant Air logo]()
$52
This Breeze Airways deal was found by Cheapflights users on 4/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2410:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 4/16![Breeze Airways logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/295:25 pm
BNA
- ALB
Nonstop2h 06m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$56
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Fri 6/125:20 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$66
This Breeze Airways deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Fri 6/1210:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/306:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 4/12![Allegiant Air logo]()
$71
This Travelocity deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:30 pm
CVG
- BOS
1 stop11h 42m
Frontier
Deal found 4/12![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/2610:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 4/13![Breeze Airways logo]()
$78
This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:30 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/47:46 pm
CVG
- BOS
1 stop12h 48m
Frontier
Deal found 4/13![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Mon 7/135:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$80
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 April 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $99 (Cheapflightsfares) |
One-way from | $47 (Cheapflightsfares) |
Popular in | March |
Cheapest in | September |
Average price | $441 |
Good round-trip deal | $485 or less |
Good one-way deal | $373 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 April 18, 2026.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Fri 6/5
6:43 pm-12:33 am
1 stop4h 50m
Hartford Bradley Intl
Mon 6/8
4:55 pm-10:24 pm
1 stop6h 29m
$237
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Wed 6/24
6:30 pm-11:59 pm
1 stop4h 29m
Hartford Bradley Intl
Wed 7/8
6:09 am-10:34 am
1 stop5h 25m
$237
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Wed 7/1
6:00 am-2:24 pm
1 stop7h 24m
Hartford Bradley Intl
Wed 7/15
4:55 pm-9:45 pm
1 stop5h 50m
$237
NashvilleAlbany
BNA - ALB
BNAALB
Nashville Intl
Thu 4/30
6:05 pm-11:15 pm
1 stop4h 10m
Albany Intl
Thu 5/7
7:10 am-11:55 am
1 stop5h 45m
$241
NashvilleAlbany
BNA - ALB
BNAALB
Nashville Intl
Sat 5/16
2:45 pm-10:25 pm
1 stop6h 40m
Albany Intl
Sat 5/23
7:32 pm-11:48 pm
1 stop5h 16m
$241
NashvilleAlbany
BNA - ALB
BNAALB
Nashville Intl
Tue 9/8
6:25 am-12:00 pm
1 stop4h 35m
Albany Intl
Tue 9/15
5:30 am-11:57 am
1 stop7h 27m
$241
NashvilleAlbany
BNA - ALB
BNAALB
Nashville Intl
Fri 6/12
5:40 pm-11:09 pm
1 stop4h 29m
Albany Intl
Sun 6/14
6:00 am-9:58 am
1 stop4h 58m
$241
NashvilleAlbany
BNA - ALB
BNAALB
Nashville Intl
Fri 5/15
6:39 pm-12:48 am
1 stop5h 09m
Albany Intl
Sat 5/16
6:00 am-10:48 am
1 stop5h 48m
$241
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Thu 4/30
6:00 am-2:18 pm
1 stop7h 18m
Hartford Bradley Intl
Mon 5/4
5:05 pm-9:57 pm
1 stop5h 52m
$241
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Tue 6/23
2:45 pm-9:25 pm
1 stop5h 40m
Hartford Bradley Intl
Tue 7/7
2:35 pm-8:50 pm
2 stops7h 15m
$242
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-ALB
BNA-BOS
SDF-BDL
CVG-BOS
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-ALB
BNA-BOS
SDF-BDL
What is the cheapest month to book a flight from Kentucky to Massachusetts?
Currently, October is the cheapest month in which you can book a flight from Kentucky to Massachusetts (average of $125). Flying from Kentucky to Massachusetts in February is currently the most expensive (average of $268). 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 April 18, 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.
How much does it cost to fly round-trip from Kentucky to Massachusetts?
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 April 18, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Kentucky to Massachusetts by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
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 Kentucky to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Kentucky to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Massachusetts by cabin class
Find flights from Kentucky to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Massachusetts flights
Browse other Kentucky and Massachusetts flight options. Last updated on April 18, 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 April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$356 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$216 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$216 | Average$385 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$238 | Average$360 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$294 | Average$372 | FlexibilityNo cancel fee | On-time69% |