$52+ Cheap flights from Kentucky to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Mar 5 — Mar 121
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Kentucky to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kentucky to Massachusetts
Cheapest
Best
Last-minute
One-way
Cheapest flights from Kentucky to MassachusettsExplore the most affordable flight options available from Kentucky to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
Explore the most affordable flight options available from Kentucky to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.
This Breeze Airways deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 6/1910:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Mon 6/227:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 1/31![Breeze Airways logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:30 am
TYS
- BOS
Nonstop2h 09m
Allegiant Air
Sun 2/229:29 am
BOS
- TYS
Nonstop2h 43m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Sun 8/237:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/1![Breeze Airways logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 8/279:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Sun 8/307:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 2/2![Breeze Airways logo]()
$128
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:33 pm
SDF
- BOS
1 stop8h 11m
Spirit Airlines
Tue 3/105:27 am
BOS
- SDF
1 stop9h 11m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/267:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Thu 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$131
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
BNA
- BOS
1 stop14h 29m
Spirit Airlines
Tue 3/105:27 am
BOS
- BNA
1 stop26h 58m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$137
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:30 am
BNA
- BOS
1 stop14h 14m
Spirit Airlines
Fri 2/203:54 pm
BOS
- BNA
1 stop26h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 2/1. 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.
Tue 3/32:54 pm
BNA
- BOS
1 stop19h 54m
Spirit Airlines
Wed 3/46:10 pm
BOS
- BNA
1 stop26h 38m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$141
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
BNA
- BOS
1 stop14h 14m
Spirit Airlines
Wed 3/45:27 am
BOS
- BNA
1 stop15h 21m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 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 2/1![Breeze Airways logo]()
$146
This lastminute.com deal was found by Cheapflights users on 2/3. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Sun 3/18:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Deal found 2/3![JetBlue logo]()
$148
Best flights from Kentucky to MassachusettsDiscover carefully curated flight deals from Kentucky to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
Discover carefully curated flight deals from Kentucky to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 3, 2026.
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 2/247:20 am
BNA
- BOS
Nonstop2h 48m
Delta
Sat 2/288:07 am
BOS
- BNA
Nonstop3h 13m
Delta
Deal found 2/1![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 2/2. 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.
Fri 2/278:40 pm
BNA
- BOS
Nonstop2h 30m
Southwest
Tue 3/39:50 am
BOS
- BNA
Nonstop3h 00m
Southwest
Deal found 2/2![Southwest logo]()
$157
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:50 am
BNA
- BDL
1 stop21h 33m
Frontier
Mon 3/98:08 pm
BDL
- BNA
1 stop15h 33m
Frontier
Deal found 2/2![Frontier logo]()
$184
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 4/296:35 pm
BNA
- BOS
1 stop4h 24m
United Airlines
Sat 5/26:00 am
BOS
- BNA
1 stop7h 26m
United Airlines
Deal found 2/2![United Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 7/105:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Fri 7/179:10 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 2/3![Allegiant Air logo]()
$216
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:19 pm
BNA
- BDL
1 stop4h 06m
American Airlines
Wed 2/2512:30 pm
BDL
- BNA
1 stop4h 40m
American Airlines
Deal found 2/3![American Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 5/146:00 am
BNA
- BDL
1 stop12h 17m
Multiple Airlines
Sun 5/178:08 pm
BDL
- BNA
2 stops16h 06m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$249
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Thu 2/198:55 am
BNA
- BDL
1 stop14h 02m
JetBlue
Sat 2/216:00 am
BDL
- BNA
1 stop4h 44m
JetBlue
Deal found 2/3![JetBlue logo]()
$313
This Southwest deal was found by Cheapflights users on 2/3. 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 3/59:20 pm
BNA
- BOS
Nonstop2h 25m
Southwest
Mon 3/167:25 pm
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 2/3![Southwest logo]()
$162
This United Airlines deal was found by Cheapflights users on 2/2. 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 4/306:34 pm
BNA
- BOS
1 stop5h 25m
United Airlines
Sun 5/35:45 am
BOS
- BNA
1 stop4h 43m
United Airlines
Deal found 2/2![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 2/1. 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.
Thu 2/197:20 am
BNA
- BOS
Nonstop2h 48m
Delta
Mon 2/237:50 pm
BOS
- BNA
Nonstop3h 13m
Delta
Deal found 2/1![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 2/173:20 pm
CVG
- BDL
1 stop18h 03m
Frontier
Thu 2/192:27 pm
BDL
- CVG
1 stop27h 05m
Frontier
Deal found 2/2![Frontier logo]()
$199
This Southwest deal was found by Cheapflights users on 2/1. 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.
Thu 2/199:05 am
BNA
- BOS
1 stop6h 00m
Southwest
Mon 2/235:00 am
BOS
- BNA
Nonstop3h 05m
Southwest
Deal found 2/1![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Mon 3/236:34 pm
BNA
- BOS
1 stop4h 23m
United Airlines
Thu 3/265:45 am
BOS
- BNA
1 stop4h 36m
United Airlines
Deal found 2/3![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:30 am
BNA
- BDL
1 stop7h 21m
Delta
Mon 5/45:17 pm
BDL
- BNA
1 stop5h 09m
Delta
Deal found 2/3![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 2/2. 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 3/310:10 am
BNA
- BOS
Nonstop2h 30m
Southwest
Tue 3/108:55 am
BOS
- BNA
1 stop5h 20m
Southwest
Deal found 2/2![Southwest logo]()
$187
This CheapOair deal was found by Cheapflights users on 2/1. 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 3/59:00 am
BNA
- BDL
1 stop7h 15m
Frontier
Mon 3/98:08 pm
BDL
- BNA
1 stop15h 33m
Frontier
Deal found 2/1![Frontier logo]()
$209
This Delta deal was found by Cheapflights users on 2/1. 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 3/47:38 am
TYS
- BDL
1 stop4h 33m
Delta
Wed 3/115:34 am
BDL
- TYS
1 stop4h 57m
Delta
Deal found 2/1![Delta logo]()
$201
This CheapOair deal was found by Cheapflights users on 2/1. 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 3/59:00 am
BNA
- BDL
1 stop7h 15m
Multiple Airlines
Mon 3/96:00 am
BDL
- BNA
2 stops18h 03m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 2/1. 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.
Fri 3/204:00 pm
BNA
- BOS
1 stop5h 15m
Southwest
Mon 3/237:25 pm
BOS
- BNA
Nonstop2h 55m
Southwest
Deal found 2/1![Southwest logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:42 am
CVG
- BDL
1 stop10h 31m
Frontier
Sun 3/158:08 pm
BDL
- CVG
1 stop11h 15m
Frontier
Deal found 2/1![Frontier logo]()
$218
This Delta deal was found by Cheapflights users on 2/1. 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 3/255:40 am
TYS
- BDL
1 stop5h 04m
Delta
Tue 3/315:04 pm
BDL
- TYS
1 stop6h 53m
Delta
Deal found 2/1![Delta logo]()
$201
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:23 pm
BNA
- BDL
1 stop5h 36m
American Airlines
Mon 5/45:25 pm
BDL
- BNA
1 stop7h 13m
American Airlines
Deal found 2/3![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:52 pm
BNA
- BDL
2 stops39h 40m
Multiple Airlines
Sat 2/2111:59 am
BDL
- BNA
1 stop8h 58m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$262
This CheapOair deal was found by Cheapflights users on 2/3. 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 4/225:20 pm
CVG
- BDL
1 stop25h 57m
Frontier
Thu 4/308:08 pm
BDL
- CVG
1 stop27h 12m
Frontier
Deal found 2/3![Frontier logo]()
$226
This American Airlines deal was found by Cheapflights users on 2/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:52 pm
SDF
- BDL
1 stop4h 32m
American Airlines
Tue 4/216:00 am
BDL
- SDF
1 stop6h 45m
American Airlines
Deal found 2/3![American Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:15 am
CVG
- BDL
2 stops17h 38m
Multiple Airlines
Sun 3/88:26 pm
BDL
- CVG
1 stop10h 57m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$266
This United Airlines deal was found by Cheapflights users on 2/2. 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 4/307:00 am
TYS
- BOS
1 stop7h 48m
United Airlines
Sat 5/212:30 pm
BOS
- TYS
1 stop8h 15m
United Airlines
Deal found 2/2![United Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/197:00 am
TYS
- BDL
1 stop15h 04m
Multiple Airlines
Sun 2/229:10 pm
BDL
- TYS
1 stop19h 49m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 2/1. 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 3/255:40 am
TYS
- BDL
1 stop5h 04m
Delta
Sat 3/285:50 pm
BDL
- TYS
1 stop6h 07m
Delta
Deal found 2/1![Delta logo]()
$250
Last-minute flights from Kentucky to MassachusettsDiscover last-minute flight deals from Kentucky to Massachusetts. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Massachusetts. Data last updated February 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:30 am
TYS
- BOS
Nonstop2h 09m
Allegiant Air
Sun 2/229:29 am
BOS
- TYS
Nonstop2h 43m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$122
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/178:30 am
BNA
- BOS
1 stop14h 14m
Spirit Airlines
Fri 2/203:54 pm
BOS
- BNA
1 stop26h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
BNA
- BOS
1 stop14h 14m
Spirit Airlines
Wed 3/45:27 am
BOS
- BNA
1 stop15h 21m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$144
This lastminute.com deal was found by Cheapflights users on 2/3. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Sun 3/18:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Deal found 2/3![JetBlue logo]()
$148
This Super.com deal was found by Cheapflights users on 2/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BNA
- BOS
Nonstop2h 31m
JetBlue
Tue 3/39:08 am
BOS
- BNA
Nonstop3h 05m
JetBlue
Deal found 2/3![JetBlue logo]()
$155
This Southwest deal was found by Cheapflights users on 2/3. 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.
Fri 2/278:40 pm
BNA
- BOS
Nonstop2h 30m
Southwest
Tue 3/39:50 am
BOS
- BNA
Nonstop3h 00m
Southwest
Deal found 2/3![Southwest logo]()
$157
This Expedia deal was found by Cheapflights users on 2/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:33 pm
SDF
- BOS
1 stop8h 11m
Spirit Airlines
Tue 3/105:27 am
BOS
- SDF
1 stop9h 11m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$129
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
BNA
- BOS
1 stop14h 29m
Spirit Airlines
Tue 3/105:27 am
BOS
- BNA
1 stop26h 58m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$137
This CheapOair deal was found by Cheapflights users on 2/1. 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.
Tue 3/32:54 pm
BNA
- BOS
1 stop19h 54m
Spirit Airlines
Wed 3/46:10 pm
BOS
- BNA
1 stop26h 38m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$141
This CheapOair deal was found by Cheapflights users on 2/1. 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.
Wed 3/48:30 am
BNA
- BOS
1 stop14h 14m
Spirit Airlines
Sat 3/76:10 pm
BOS
- BNA
1 stop13h 15m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$154
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
Wed 3/411:03 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Sat 3/78:59 pm
BOS
- BNA
Nonstop3h 04m
JetBlue
Deal found 2/3![JetBlue logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 3/267:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Thu 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$131
One-way flights from Kentucky to MassachusettsSearch for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
Search for one-way flight options from Kentucky to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Mytrip deal was found by Cheapflights users on 2/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:12 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 2/1![Breeze Airways logo]()
$52
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/267:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 2/1![Allegiant Air logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:54 pm
BNA
- BDL
1 stop17h 29m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 2/248:52 pm
BNA
- BOS
1 stop25h 52m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$76
This CheapOair deal was found by Cheapflights users on 2/3. 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 2/258:30 am
BNA
- BOS
1 stop14h 14m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$78
This Southwest deal was found by Cheapflights users on 2/2. 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 3/36:15 pm
BNA
- BOS
Nonstop2h 30m
Southwest
Deal found 2/2![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Fri 7/315:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 2/2![Allegiant Air logo]()
$79
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:43 pm
CVG
- BOS
1 stop5h 30m
Frontier
Deal found 2/2![Frontier logo]()
$80
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:23 am
BNA
- BDL
1 stop7h 54m
Frontier
Deal found 2/1![Frontier logo]()
$80
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/122:27 pm
BNA
- BOS
1 stop8h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Tue 3/1710:00 am
BNA
- BOS
Nonstop2h 33m
JetBlue
Deal found 1/31![JetBlue logo]()
$83
Find flight deals from Kentucky to Massachusetts
Keep the following information in mind while searching for Kentucky to Massachusetts flight deals. Data was last updated February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $118 (Breeze Airways) |
One-way from | $66 (Kiwi.com) |
Popular in | January |
Cheapest in | September |
Average price | $383 |
Good round-trip deal | $452 or less |
Good one-way deal | $307 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Kentucky to Massachusetts that are best for you.
Fly from
Kentucky
Fly to
Massachusetts
Route
Depart
Return
Price
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Tue 2/24
7:20 am-11:08 am
Nonstop2h 48m
Boston Logan Intl
Sat 2/28
8:07 am-10:20 am
Nonstop3h 13m
$157
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 2/27
8:40 pm-12:10 am
Nonstop2h 30m
Boston Logan Intl
Tue 3/3
9:50 am-11:50 am
Nonstop3h 00m
$157
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Thu 3/5
9:20 pm-12:45 am
Nonstop2h 25m
Boston Logan Intl
Mon 3/16
7:25 pm-9:20 pm
Nonstop2h 55m
$162
NashvilleHartford
BNA - BDL
BNABDL
Nashville Intl
Mon 3/2
10:50 am-9:23 am
1 stop21h 33m
Hartford Bradley Intl
Mon 3/9
8:08 pm-10:41 am
1 stop15h 33m
$184
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Wed 4/29
6:35 pm-11:59 pm
1 stop4h 24m
Boston Logan Intl
Sat 5/2
6:00 am-12:26 pm
1 stop7h 26m
$187
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Thu 4/30
6:34 pm-12:59 am
1 stop5h 25m
Boston Logan Intl
Sun 5/3
5:45 am-9:28 am
1 stop4h 43m
$187
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Thu 2/19
9:05 am-4:05 pm
1 stop6h 00m
Boston Logan Intl
Mon 2/23
5:00 am-7:05 am
Nonstop3h 05m
$187
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Mon 3/23
6:34 pm-11:57 pm
1 stop4h 23m
Boston Logan Intl
Thu 3/26
5:45 am-9:21 am
1 stop4h 36m
$187
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Tue 3/3
10:10 am-1:40 pm
Nonstop2h 30m
Boston Logan Intl
Tue 3/10
8:55 am-1:15 pm
1 stop5h 20m
$187
NashvilleBoston
BNA - BOS
BNABOS
Nashville Intl
Fri 3/20
4:00 pm-10:15 pm
1 stop5h 15m
Boston Logan Intl
Mon 3/23
7:25 pm-9:20 pm
Nonstop2h 55m
$192
Showing 1-10 of 60 results
Best time to book a flight from Kentucky to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Kentucky with our price prediction graph.
BNA-BOS
BNA-BDL
BNA-ALB
CVG-BDL
TYS-BDL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Massachusetts
USKY-USMA
BNA-BOS
BNA-BDL
BNA-ALB
CVG-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 February 3, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Massachusetts as you normally would.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated February 3, 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.
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
Alternative routes for Kentucky to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Massachusetts by cabin class
Find flights from Kentucky to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Massachusetts flights
Browse other Kentucky and Massachusetts flight options. Last updated on February 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Kentucky after your stay in Massachusetts
Kentucky to Massachusetts flights
Consider these flights traveling from Kentucky to Massachusetts.
Top 5 airlines flying from Kentucky to Massachusetts
Discover the top 5 airlines that operate flights from Kentucky to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$139 | Average$339 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$174 | Average$216 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$209 | Average$359 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$384 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$438 | FlexibilityNo cancel fee | On-time69% |