$48+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Apr 4 — Apr 111
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 March 5, 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 March 5, 2026.
This Booking.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 4/269:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/3![Allegiant Air logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/2![Allegiant Air logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 6/49:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Sun 6/77:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 3/3![Breeze Airways logo]()
$117
This Booking.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
Sun 4/57:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Thu 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/2![Allegiant Air logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/79:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Tue 5/197:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/28![Breeze Airways logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/298:01 pm
BNA
- BOS
1 stop12h 28m
Spirit Airlines
Tue 6/211:25 am
BOS
- BNA
1 stop7h 12m
Spirit Airlines
Deal found 2/28![Spirit Airlines logo]()
$131
This Expedia deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:40 pm
BNA
- BOS
Nonstop2h 33m
Multiple Airlines
Sat 4/49:50 am
BOS
- BNA
1 stop10h 56m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$133
This Priceline deal was found by Cheapflights users on 3/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:27 pm
BNA
- BOS
1 stop7h 30m
Multiple Airlines
Sat 5/911:16 am
BOS
- BNA
1 stop7h 06m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$134
This CheapOair deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:05 am
BNA
- BOS
Nonstop2h 27m
Multiple Airlines
Sun 4/268:16 pm
BOS
- BNA
1 stop13h 19m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$138
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/229:00 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 3/3![Allegiant Air logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 3/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:27 pm
BNA
- BOS
1 stop8h 32m
Spirit Airlines
Tue 4/145:45 am
BOS
- BNA
1 stop8h 44m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$141
This Expedia deal was found by Cheapflights users on 3/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:01 pm
BNA
- BOS
1 stop12h 28m
Spirit Airlines
Mon 5/1810:25 am
BOS
- BNA
1 stop9h 31m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$142
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 March 5, 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 March 5, 2026.
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/56:05 am
BNA
- BOS
Nonstop2h 46m
Delta
Tue 5/127:20 pm
BOS
- BNA
Nonstop2h 55m
Delta
Deal found 2/28![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/62:45 pm
BNA
- BOS
2 stops6h 55m
Southwest
Sat 5/912:40 pm
BOS
- BNA
Nonstop2h 45m
Southwest
Deal found 3/2![Southwest logo]()
$192
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/237:52 pm
BNA
- BOS
Nonstop2h 34m
JetBlue
Sat 6/68:30 pm
BOS
- BNA
Nonstop2h 50m
JetBlue
Deal found 3/1![JetBlue logo]()
$192
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Fri 5/156:30 pm
BNA
- BDL
1 stop4h 14m
United Airlines
Sun 5/176:00 am
BDL
- BNA
1 stop5h 48m
United Airlines
Deal found 3/4![United Airlines logo]()
$231
This Southwest deal was found by Cheapflights users on 3/4. 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.
Tue 3/243:10 pm
BNA
- BOS
2 stops7h 15m
Southwest
Tue 3/316:25 pm
BOS
- BNA
Nonstop3h 05m
Southwest
Deal found 3/4![Southwest logo]()
$202
This JetBlue deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/228:49 am
BNA
- BOS
1 stop4h 29m
JetBlue
Sun 4/267:45 pm
BOS
- BNA
Nonstop2h 57m
JetBlue
Deal found 3/3![JetBlue logo]()
$202
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/65:15 am
BNA
- BDL
1 stop4h 29m
Delta
Mon 4/137:01 pm
BDL
- BNA
1 stop5h 23m
Delta
Deal found 2/28![Delta logo]()
$211
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 7/176:12 pm
CVG
- ALB
1 stop5h 31m
American Airlines
Sun 7/195:42 am
ALB
- CVG
1 stop7h 18m
American Airlines
Deal found 2/28![American Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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
- BOS
1 stop4h 50m
Southwest
Sun 5/36:40 am
BOS
- BNA
1 stop5h 05m
Southwest
Deal found 3/3![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 6/106:40 am
BNA
- BDL
1 stop4h 26m
Delta
Tue 6/166:00 am
BDL
- BNA
1 stop7h 20m
Delta
Deal found 3/1![Delta logo]()
$211
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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
Sat 5/95:20 am
BOS
- BNA
1 stop4h 53m
JetBlue
Deal found 3/1![JetBlue logo]()
$212
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 6/126:30 pm
BNA
- BDL
1 stop4h 29m
United Airlines
Tue 6/166:00 am
BDL
- BNA
2 stops7h 29m
United Airlines
Deal found 3/3![United Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/146:43 pm
BNA
- BDL
1 stop4h 50m
Delta
Sun 5/176:00 am
BDL
- BNA
1 stop6h 37m
Delta
Deal found 3/2![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 3/4. 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.
Tue 3/244:10 pm
BNA
- BOS
2 stops6h 15m
Southwest
Sun 3/298:10 am
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 3/4![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 6/46:43 pm
BNA
- BDL
1 stop4h 50m
Delta
Sun 6/76:00 am
BDL
- BNA
1 stop6h 07m
Delta
Deal found 2/28![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 3/4. 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.
Sat 5/306:35 pm
BNA
- BOS
1 stop4h 05m
Southwest
Sat 6/68:40 am
BOS
- BNA
Nonstop2h 40m
Southwest
Deal found 3/4![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
Sun 8/97:44 pm
LEX
- BOS
1 stop5h 15m
United Airlines
Thu 8/2010:51 am
BOS
- LEX
1 stop6h 03m
United Airlines
Deal found 3/3![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/29:07 am
SDF
- BDL
1 stop5h 08m
United Airlines
Wed 4/85:10 pm
BDL
- SDF
1 stop6h 49m
United Airlines
Deal found 3/2![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 3/137:05 am
BNA
- BOS
Nonstop2h 38m
Delta
Sun 3/227:15 pm
BOS
- BNA
Nonstop3h 05m
Delta
Deal found 2/28![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 3/4. 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 4/29:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Thu 4/910:40 am
BOS
- BNA
1 stop7h 40m
Southwest
Deal found 3/4![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/22:55 pm
SDF
- BDL
1 stop6h 31m
United Airlines
Sat 5/95:05 pm
BDL
- SDF
1 stop5h 25m
United Airlines
Deal found 3/1![United Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:35 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Wed 3/118:20 am
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 3/2![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Thu 5/77:00 am
LEX
- BOS
2 stops7h 26m
United Airlines
Sun 5/106:39 pm
BOS
- LEX
1 stop5h 10m
United Airlines
Deal found 3/4![United Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 3/5. 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 3/3110:50 am
SDF
- BDL
1 stop5h 19m
Delta
Sat 4/46:00 am
BDL
- SDF
1 stop6h 47m
Delta
Deal found 3/5![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 3/316:00 am
CVG
- BDL
1 stop3h 37m
United Airlines
Tue 4/73:04 pm
BDL
- CVG
1 stop3h 59m
United Airlines
Deal found 3/1![United Airlines logo]()
$297
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 4/146:40 am
BNA
- BDL
1 stop7h 00m
Southwest
Thu 4/167:20 pm
BDL
- BNA
1 stop4h 40m
Southwest
Deal found 3/2![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/86:07 pm
TYS
- BOS
1 stop4h 18m
Delta
Wed 5/139:10 am
BOS
- TYS
1 stop5h 23m
Delta
Deal found 2/28![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 5/17:00 am
TYS
- BDL
1 stop7h 18m
United Airlines
Sun 5/36:05 am
BDL
- TYS
1 stop4h 44m
United Airlines
Deal found 2/28![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 5/278:15 am
TYS
- BDL
1 stop6h 25m
Southwest
Sun 5/315:20 pm
BDL
- TYS
1 stop4h 40m
Southwest
Deal found 3/1![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 3/4. 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.
Sat 4/116:00 am
CVG
- BOS
1 stop6h 31m
Delta
Wed 4/1512:30 pm
BOS
- CVG
1 stop8h 49m
Delta
Deal found 3/4![Delta logo]()
$299
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated March 5, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated March 5, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Sun 3/229:00 am
BOS
- TYS
Nonstop2h 32m
Allegiant Air
Deal found 3/3![Allegiant Air logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 2/28![Allegiant Air logo]()
$145
This Expedia deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:40 pm
BNA
- BOS
Nonstop2h 33m
Multiple Airlines
Sat 4/49:50 am
BOS
- BNA
1 stop10h 56m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$133
This CheapOair deal was found by Cheapflights users on 3/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/12:27 pm
BNA
- BOS
1 stop22h 28m
Spirit Airlines
Wed 4/89:45 am
BOS
- BNA
1 stop7h 53m
Spirit Airlines
Deal found 3/4![Spirit Airlines logo]()
$147
This CheapOair deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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.
Sat 4/46:15 am
BNA
- BOS
1 stop10h 54m
Multiple Airlines
Sat 4/115:00 pm
BOS
- BNA
Nonstop3h 02m
Multiple Airlines
Deal found 2/28![Multiple Airlines logo]()
$155
This Booking.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
Sun 4/57:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Thu 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/2![Allegiant Air logo]()
$121
This Priceline deal was found by Cheapflights users on 3/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:22 am
BNA
- BOS
Nonstop2h 33m
Multiple Airlines
Wed 4/85:49 pm
BOS
- BNA
1 stop6h 49m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” 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 4/97:44 am
BNA
- BOS
1 stop6h 44m
Spirit Airlines
Tue 4/145:45 am
BOS
- BNA
1 stop8h 44m
Spirit Airlines
Deal found 2/28![Spirit Airlines logo]()
$131
This CheapOair deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
Thu 4/98:00 pm
BNA
- BOS
Nonstop2h 33m
Multiple Airlines
Tue 4/145:45 am
BOS
- BNA
1 stop8h 44m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$153
This Booking.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Sun 4/269:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/3![Allegiant Air logo]()
$93
This CheapOair deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:05 am
BNA
- BOS
Nonstop2h 27m
Multiple Airlines
Sun 4/268:16 pm
BOS
- BNA
1 stop13h 19m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 3/4. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:05 am
BNA
- BOS
Nonstop2h 27m
Multiple Airlines
Sat 4/258:16 pm
BOS
- BNA
1 stop13h 19m
Multiple Airlines
Deal found 3/4![Multiple Airlines logo]()
$143
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 March 5, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 6/1510:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 3/3![Breeze Airways logo]()
$48
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:00 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 3/3![Allegiant Air logo]()
$52
This Cheapflightsfares deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 4/57:30 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 3/1![Allegiant Air logo]()
$55
This Breeze Airways deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 3/2![Breeze Airways logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/1212:20 pm
CVG
- BOS
1 stop13h 06m
Frontier
Deal found 3/3![Frontier logo]()
$65
This Booking.com deal was found by Cheapflights users on 3/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 3/4![Breeze Airways logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 3/177:41 pm
CVG
- BOS
1 stop14h 48m
Frontier
Deal found 3/3![Frontier logo]()
$66
This Cheapflightsfares deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:30 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 3/3![Allegiant Air logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- BOS
1 stop5h 45m
Frontier
Deal found 3/3![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/107:43 pm
CVG
- BOS
1 stop29h 08m
Frontier
Deal found 3/3![Frontier logo]()
$68
This Breeze Airways deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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 7/3110:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 3/1![Breeze Airways logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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 5/147:43 pm
CVG
- BDL
1 stop16h 32m
Frontier
Deal found 3/2![Frontier logo]()
$70
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 March 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $93 (Booking.com) |
One-way from | $46 (Kiwi.com) |
Popular in | February |
Cheapest in | September |
Average price | $379 |
Good round-trip deal | $433 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 March 5, 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
Tue 5/5
6:05 am-9:51 am
Nonstop2h 46m
Boston Logan Intl
Tue 5/12
7:20 pm-9:15 pm
Nonstop2h 55m
$157
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 5/6
2:45 pm-10:40 pm
2 stops6h 55m
Boston Logan Intl
Sat 5/9
12:40 pm-2:25 pm
Nonstop2h 45m
$192
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Sat 5/23
7:52 pm-11:26 pm
Nonstop2h 34m
Boston Logan Intl
Sat 6/6
8:30 pm-10:20 pm
Nonstop2h 50m
$192
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Tue 3/24
3:10 pm-11:25 pm
2 stops7h 15m
Boston Logan Intl
Tue 3/31
6:25 pm-8:30 pm
Nonstop3h 05m
$202
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 4/22
8:49 am-2:18 pm
1 stop4h 29m
Boston Logan Intl
Sun 4/26
7:45 pm-9:42 pm
Nonstop2h 57m
$202
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Thu 4/30
6:05 pm-11:55 pm
1 stop4h 50m
Boston Logan Intl
Sun 5/3
6:40 am-10:45 am
1 stop5h 05m
$207
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Mon 4/6
5:15 am-10:44 am
1 stop4h 29m
Hartford Bradley Intl
Mon 4/13
7:01 pm-11:24 pm
1 stop5h 23m
$211
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Wed 6/10
6:40 am-12:06 pm
1 stop4h 26m
Hartford Bradley Intl
Tue 6/16
6:00 am-12:20 pm
1 stop7h 20m
$211
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Thu 5/14
6:43 pm-12:33 am
1 stop4h 50m
Hartford Bradley Intl
Sun 5/17
6:00 am-11:37 am
1 stop6h 37m
$211
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Thu 6/4
6:43 pm-12:33 am
1 stop4h 50m
Hartford Bradley Intl
Sun 6/7
6:00 am-11:07 am
1 stop6h 07m
$211
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
CVG-BDL
TYS-BOS
BNA-BDL
BNA-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
SDF-BDL
CVG-BDL
TYS-BOS
BNA-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 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 March 5, 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 March 5, 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
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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
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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 March 5, 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 March 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$336 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$216 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$209 | Average$357 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$381 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$406 | FlexibilityNo cancel fee | On-time69% |