$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 9 — May 161
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 9, 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 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/55:15 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Mon 6/89:13 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Mon 6/17:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 4/9![Breeze Airways logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/265:20 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Mon 6/299:18 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/9![Allegiant Air logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Tue 8/187:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 4/7![Breeze Airways logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/5![Allegiant Air logo]()
$124
This Cheapflightsfares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/76:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Sat 4/2510:26 pm
BOS
- TYS
1 stop17h 15m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:30 am
TYS
- BOS
1 stop24h 53m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Sun 6/77:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 4/5![Breeze Airways logo]()
$137
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 9, 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 9, 2026.
This Breeze Airways deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1510:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Fri 6/197:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 4/9![Breeze Airways logo]()
$168
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:40 am
BNA
- BOS
1 stop4h 35m
Southwest
Tue 5/52:25 pm
BOS
- BNA
2 stops8h 35m
Southwest
Deal found 4/9![Southwest logo]()
$212
This JetBlue deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/66:50 pm
BNA
- BOS
Nonstop2h 34m
JetBlue
Wed 6/38:30 pm
BOS
- BNA
Nonstop2h 50m
JetBlue
Deal found 4/4![JetBlue logo]()
$227
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/86:02 pm
BNA
- BDL
1 stop4h 33m
Delta
Wed 5/135:30 am
BDL
- BNA
1 stop4h 35m
Delta
Deal found 4/4![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/278:30 am
BNA
- BDL
1 stop4h 36m
United Airlines
Sat 5/306:09 am
BDL
- BNA
1 stop7h 20m
United Airlines
Deal found 4/4![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/11:15 pm
TYS
- BDL
2 stops10h 01m
Multiple Airlines
Sun 5/38:42 pm
BDL
- TYS
1 stop25h 42m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/205:00 am
TYS
- BDL
1 stop4h 10m
American Airlines
Sun 5/247:12 am
BDL
- TYS
1 stop5h 58m
American Airlines
Deal found 4/4![American Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:00 am
BNA
- BDL
1 stop6h 15m
Southwest
Tue 6/308:55 am
BDL
- BNA
1 stop6h 05m
Southwest
Deal found 4/7![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/216:52 pm
BNA
- ALB
1 stop5h 01m
United Airlines
Tue 4/286:00 am
ALB
- BNA
2 stops7h 28m
United Airlines
Deal found 4/5![United Airlines logo]()
$246
This Breeze Airways deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Tue 7/288:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Tue 8/117:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 4/6![Breeze Airways logo]()
$248
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/135:45 pm
BNA
- BOS
Nonstop2h 51m
Delta
Sun 6/2112:20 pm
BOS
- BNA
Nonstop2h 49m
Delta
Deal found 4/5![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:20 am
BNA
- BDL
1 stop4h 20m
Southwest
Tue 5/56:20 pm
BDL
- BNA
1 stop4h 40m
Southwest
Deal found 4/7![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 6/55:10 am
BNA
- BDL
2 stops8h 00m
Southwest
Thu 6/117:10 pm
BDL
- BNA
1 stop4h 55m
Southwest
Deal found 4/4![Southwest logo]()
$242
This JetBlue deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop4h 31m
JetBlue
Sat 5/97:45 pm
BOS
- BNA
Nonstop2h 52m
JetBlue
Deal found 4/7![JetBlue logo]()
$300
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/99:15 am
LEX
- BOS
1 stop4h 05m
Delta
Sat 5/169:00 am
BOS
- LEX
1 stop5h 26m
Delta
Deal found 4/6![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:50 pm
LEX
- BOS
1 stop5h 09m
United Airlines
Sat 5/1612:30 pm
BOS
- LEX
1 stop7h 44m
United Airlines
Deal found 4/8![United Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:45 pm
BNA
- BDL
1 stop10h 55m
Southwest
Mon 5/47:20 pm
BDL
- BNA
1 stop4h 40m
Southwest
Deal found 4/4![Southwest logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 7/68:48 pm
SDF
- BDL
3 stops25h 54m
Multiple Airlines
Fri 7/107:35 am
BDL
- SDF
Nonstop2h 20m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:10 am
SDF
- BDL
1 stop4h 51m
Delta
Thu 6/46:00 am
BDL
- SDF
1 stop6h 08m
Delta
Deal found 4/9![Delta logo]()
$285
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/16:31 am
SDF
- BDL
1 stop7h 26m
American Airlines
Mon 5/42:47 pm
BDL
- SDF
1 stop7h 21m
American Airlines
Deal found 4/4![American Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:49 pm
BNA
- BOS
1 stop5h 41m
United Airlines
Mon 7/65:45 am
BOS
- BNA
1 stop4h 44m
United Airlines
Deal found 4/9![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/72:15 pm
BNA
- BDL
2 stops7h 55m
Southwest
Mon 5/115:50 am
BDL
- BNA
2 stops6h 05m
Southwest
Deal found 4/4![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/51:00 pm
CVG
- BDL
1 stop3h 31m
Delta
Tue 5/1211:56 am
BDL
- CVG
1 stop4h 41m
Delta
Deal found 4/5![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:40 pm
BNA
- ALB
1 stop9h 20m
Southwest
Sat 6/611:05 am
ALB
- BNA
2 stops9h 45m
Southwest
Deal found 4/5![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:40 am
BNA
- BOS
1 stop5h 23m
United Airlines
Sat 5/96:00 am
BOS
- BNA
1 stop8h 02m
United Airlines
Deal found 4/7![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/135:55 pm
BNA
- ALB
1 stop4h 26m
Delta
Mon 4/206:00 pm
ALB
- BNA
1 stop6h 24m
Delta
Deal found 4/6![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:55 pm
TYS
- BDL
1 stop6h 10m
Southwest
Tue 5/124:05 pm
BDL
- TYS
1 stop4h 45m
Southwest
Deal found 4/7![Southwest logo]()
$261
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:49 pm
BNA
- BDL
1 stop7h 44m
United Airlines
Sun 7/56:09 am
BDL
- BNA
1 stop5h 25m
United Airlines
Deal found 4/5![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/185:25 am
BNA
- ALB
1 stop5h 48m
Delta
Sat 4/256:00 am
ALB
- BNA
1 stop4h 08m
Delta
Deal found 4/5![Delta logo]()
$290
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/256:00 am
BNA
- BDL
2 stops7h 06m
United Airlines
Sun 6/286:09 am
BDL
- BNA
1 stop5h 25m
United Airlines
Deal found 4/6![United Airlines logo]()
$319
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated April 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Sat 4/2510:26 pm
BOS
- TYS
1 stop17h 15m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:30 am
TYS
- BOS
1 stop24h 53m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Sat 4/2510:26 pm
BOS
- TYS
1 stop17h 15m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sat 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/76:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/6![Allegiant Air logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/5![Allegiant Air logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 5/2410:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Thu 5/2810:30 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Mon 6/17:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 4/9![Breeze Airways logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Tue 6/27:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 4/5![Breeze Airways logo]()
$137
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 9, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 7/35:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 4/5![Allegiant Air logo]()
$47
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:15 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Deal found 4/7![Allegiant Air logo]()
$50
This Super.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 4/9![Allegiant Air logo]()
$51
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 4/7![Allegiant Air logo]()
$52
This Breeze Airways deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/7![Breeze Airways logo]()
$54
This Breeze Airways deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 4/7![Breeze Airways logo]()
$59
This Trip.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:54 pm
CVG
- BOS
1 stop12h 33m
Frontier
Deal found 4/4![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:46 pm
CVG
- BOS
1 stop19h 58m
Frontier
Deal found 4/8![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/510:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 4/6![Breeze Airways logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:20 pm
BNA
- ALB
Nonstop2h 08m
Allegiant Air
Deal found 4/7![Allegiant Air logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/5![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:25 pm
BNA
- ALB
Nonstop2h 06m
Allegiant Air
Deal found 4/5![Allegiant Air logo]()
$74
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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $100 (Cheapflightsfares) |
One-way from | $47 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $424 |
Good round-trip deal | $463 or less |
Good one-way deal | $278 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 9, 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
LouisvilleHartford
SDF - BDL
SDFBDL
Louisville Intl
Mon 6/15
10:35 am-12:45 pm
Nonstop2h 10m
Hartford Bradley Intl
Fri 6/19
7:35 am-9:55 am
Nonstop2h 20m
$168
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Tue 5/5
6:40 am-12:15 pm
1 stop4h 35m
Boston Logan Intl
Tue 5/5
2:25 pm-10:00 pm
2 stops8h 35m
$212
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 5/6
6:50 pm-10:24 pm
Nonstop2h 34m
Boston Logan Intl
Wed 6/3
8:30 pm-10:20 pm
Nonstop2h 50m
$227
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Fri 5/8
6:02 pm-11:35 pm
1 stop4h 33m
Hartford Bradley Intl
Wed 5/13
5:30 am-9:05 am
1 stop4h 35m
$237
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Wed 5/27
8:30 am-2:06 pm
1 stop4h 36m
Hartford Bradley Intl
Sat 5/30
6:09 am-12:29 pm
1 stop7h 20m
$237
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Tue 6/23
5:00 am-12:15 pm
1 stop6h 15m
Hartford Bradley Intl
Tue 6/30
8:55 am-2:00 pm
1 stop6h 05m
$237
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Thu 4/30
5:20 am-10:40 am
1 stop4h 20m
Hartford Bradley Intl
Tue 5/5
6:20 pm-10:00 pm
1 stop4h 40m
$241
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Fri 6/5
5:10 am-2:10 pm
2 stops8h 00m
Hartford Bradley Intl
Thu 6/11
7:10 pm-11:05 pm
1 stop4h 55m
$242
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Sun 5/3
10:45 pm-10:40 am
1 stop10h 55m
Hartford Bradley Intl
Mon 5/4
7:20 pm-11:00 pm
1 stop4h 40m
$244
NashvilleAlbany
BNA - ALB
BNAALB
Nashville Intl
Tue 4/21
6:52 pm-12:53 am
1 stop5h 01m
Albany Intl
Tue 4/28
6:00 am-12:28 pm
2 stops7h 28m
$246
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.
SDF-BDL
BNA-BOS
BNA-BDL
TYS-BDL
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
SDF-BDL
BNA-BOS
BNA-BDL
TYS-BDL
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 April is currently the most expensive (average of $294). 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 9, 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 9, 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
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
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.
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 April 9, 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 9, 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$359 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$294 | Average$372 | FlexibilityNo cancel fee | On-time69% |