$46+ Cheap flights from Massachusetts to Kentucky
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Mei 3 — Mei 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Massachusetts to Kentucky 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 Massachusetts to Kentucky
Cheapest
Best
Last-minute
One-way
Cheapest flights from Massachusetts to KentuckyExplore the most affordable flight options available from Massachusetts to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2026.
Explore the most affordable flight options available from Massachusetts to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 3, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sen 6/89:13 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Jum 7/35:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$85
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sen 9/2112:39 pm
ALB
- BNA
Nonstop2h 18m
Allegiant Air
Jum 9/257:20 am
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$133
This Expedia deal was found by Cheapflights users on 4/2. 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.
Kam 4/301:39 pm
BDL
- CVG
1 stop9h 41m
Multiple Airlines
Kam 5/78:40 pm
CVG
- BDL
Nonstop2h 02m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sab 5/3010:46 am
BOS
- TYS
1 stop11h 32m
Allegiant Air
Min 5/317:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 3/28![Allegiant Air logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sen 8/109:22 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Jum 8/145:23 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Min 4/129:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sab 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$145
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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.
Kam 6/410:38 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Sab 6/66:45 am
TYS
- BOS
Nonstop2h 18m
Allegiant Air
Deal found 4/1![Allegiant Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sel 4/145:45 am
BOS
- TYS
1 stop28h 51m
Multiple Airlines
Sab 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sab 5/239:45 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sab 5/306:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 3/31![Allegiant Air logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sel 4/145:45 am
BOS
- TYS
1 stop28h 51m
Multiple Airlines
Kam 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Jum 7/319:10 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Sen 8/35:11 pm
BNA
- ALB
Nonstop2h 09m
Allegiant Air
Deal found 3/31![Allegiant Air logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Kam 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Min 4/126:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 3/29![Allegiant Air logo]()
$167
Best flights from Massachusetts to KentuckyDiscover carefully curated flight deals from Massachusetts to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 3, 2026.
Discover carefully curated flight deals from Massachusetts to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 3, 2026.
This Breeze Airways deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Jum 5/297:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Jum 6/510:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 3/29![Breeze Airways logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sab 5/309:45 am
BOS
- TYS
Nonstop2h 29m
Multiple Airlines
Min 5/318:15 am
TYS
- BOS
2 stops26h 51m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Kam 5/77:20 pm
BOS
- BNA
Nonstop2h 55m
Delta
Sel 5/127:00 am
BNA
- BOS
Nonstop2h 43m
Delta
Deal found 3/31![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Jum 5/82:55 pm
ALB
- BNA
2 stops6h 35m
Southwest
Min 5/179:40 pm
BNA
- ALB
1 stop9h 20m
Southwest
Deal found 3/31![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 3/28. 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.
Sab 6/134:50 pm
BDL
- BNA
1 stop5h 49m
United Airlines
Sab 6/206:00 am
BNA
- BDL
1 stop7h 24m
United Airlines
Deal found 3/28![United Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 4/2. 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.
Jum 5/18:10 pm
BOS
- BNA
Nonstop3h 06m
Delta
Jum 5/85:45 pm
BNA
- BOS
Nonstop2h 45m
Delta
Deal found 4/2![Delta logo]()
$267
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Sen 8/39:00 am
BDL
- BNA
2 stops6h 30m
Southwest
Sen 8/105:40 am
BNA
- BDL
1 stop5h 20m
Southwest
Deal found 3/29![Southwest logo]()
$273
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Rab 5/63:04 pm
BDL
- SDF
2 stops7h 26m
United Airlines
Sab 5/95:50 am
SDF
- BDL
1 stop3h 47m
United Airlines
Deal found 3/31![United Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Jum 7/316:00 am
ALB
- BNA
1 stop6h 30m
Delta
Sen 8/35:40 pm
BNA
- ALB
1 stop4h 26m
Delta
Deal found 3/31![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 4/2. 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.
Kam 5/141:35 pm
BOS
- BNA
1 stop10h 20m
Southwest
Rab 5/2012:40 pm
BNA
- BOS
2 stops7h 40m
Southwest
Deal found 4/2![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Sel 6/236:00 am
BDL
- TYS
1 stop4h 42m
United Airlines
Rab 6/247:19 pm
TYS
- BDL
1 stop4h 40m
United Airlines
Deal found 3/29![United Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Kam 6/41:00 pm
BOS
- BNA
1 stop7h 06m
Delta
Sab 6/67:05 am
BNA
- BOS
Nonstop2h 43m
Delta
Deal found 3/29![Delta logo]()
$272
This Southwest deal was found by Cheapflights users on 4/2. 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.
Rab 4/296:00 pm
BOS
- BNA
Nonstop2h 55m
Southwest
Sen 5/45:20 am
BNA
- BOS
1 stop4h 35m
Southwest
Deal found 4/2![Southwest logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Jum 9/186:00 am
BDL
- SDF
1 stop3h 43m
Breeze Airways
Min 9/209:09 pm
SDF
- BDL
1 stop20h 21m
Breeze Airways
Deal found 4/2![Breeze Airways logo]()
$348
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Sel 6/23:00 pm
BOS
- LEX
1 stop7h 05m
Delta
Sab 6/66:11 pm
LEX
- BOS
1 stop7h 17m
Delta
Deal found 3/29![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 3/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sel 4/287:20 am
BOS
- BNA
1 stop4h 55m
Southwest
Sen 5/46:05 pm
BNA
- BOS
1 stop4h 50m
Southwest
Deal found 3/31![Southwest logo]()
$277
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Jum 4/246:48 pm
BOS
- LEX
1 stop5h 11m
United Airlines
Sel 4/287:00 am
LEX
- BOS
2 stops9h 22m
United Airlines
Deal found 3/30![United Airlines logo]()
$315
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Kam 4/239:06 am
BOS
- TYS
Nonstop2h 29m
Multiple Airlines
Sen 4/271:15 pm
TYS
- BOS
1 stop21h 06m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Rab 6/179:15 am
ALB
- BNA
1 stop5h 45m
Southwest
Kam 6/186:05 pm
BNA
- ALB
1 stop4h 40m
Southwest
Deal found 3/30![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 4/2. 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.
Rab 6/172:46 pm
BOS
- BNA
Nonstop2h 53m
Delta
Sab 6/207:01 pm
BNA
- BOS
1 stop5h 30m
Delta
Deal found 4/2![Delta logo]()
$282
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sel 6/96:09 am
BDL
- BNA
1 stop7h 20m
United Airlines
Rab 6/1012:49 pm
BNA
- BDL
1 stop7h 59m
United Airlines
Deal found 3/30![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Rab 6/245:30 am
BOS
- BNA
1 stop4h 34m
Delta
Sel 6/307:10 am
BNA
- BOS
Nonstop2h 42m
Delta
Deal found 3/30![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 4/1. 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.
Kam 6/45:25 am
BOS
- BNA
2 stops6h 55m
Southwest
Sen 6/84:40 pm
BNA
- BOS
2 stops6h 25m
Southwest
Deal found 4/1![Southwest logo]()
$282
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Sel 4/286:05 am
ALB
- BNA
1 stop7h 23m
United Airlines
Rab 4/297:25 am
BNA
- ALB
1 stop6h 47m
United Airlines
Deal found 4/1![United Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 4/2. 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.
Sel 5/127:35 am
BOS
- TYS
2 stops9h 35m
Southwest
Kam 5/146:45 pm
TYS
- BOS
1 stop4h 30m
Southwest
Deal found 4/2![Southwest logo]()
$292
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sen 6/296:09 am
BDL
- BNA
1 stop7h 20m
United Airlines
Kam 7/211:15 am
BNA
- BDL
2 stops11h 44m
United Airlines
Deal found 3/30![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Sel 6/24:30 pm
BOS
- LEX
1 stop5h 35m
Delta
Jum 6/123:54 pm
LEX
- BOS
1 stop7h 33m
Delta
Deal found 3/29![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Kam 6/256:00 am
BDL
- BNA
1 stop4h 29m
United Airlines
Sel 6/3012:49 pm
BNA
- BDL
2 stops10h 10m
United Airlines
Deal found 3/31![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 4/1. 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.
Kam 6/187:10 pm
BDL
- BNA
1 stop4h 55m
Southwest
Min 6/215:20 am
BNA
- BDL
1 stop4h 25m
Southwest
Deal found 4/1![Southwest logo]()
$308
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sen 6/17:30 am
BOS
- BNA
2 stops7h 19m
United Airlines
Kam 6/48:30 am
BNA
- BOS
2 stops7h 08m
United Airlines
Deal found 3/30![United Airlines logo]()
$327
Last-minute flights from Massachusetts to KentuckyDiscover last-minute flight deals from Massachusetts to Kentucky. Data last updated April 3, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Kentucky. Data last updated April 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Min 4/59:45 am
BOS
- BNA
1 stop7h 53m
Spirit Airlines
Kam 4/96:15 am
BNA
- BOS
1 stop9h 39m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Kam 4/99:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Min 4/126:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 3/29![Allegiant Air logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Min 4/129:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sab 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sel 4/145:45 am
BOS
- TYS
1 stop28h 51m
Multiple Airlines
Sab 4/186:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sel 4/145:45 am
BOS
- TYS
1 stop28h 51m
Multiple Airlines
Kam 4/166:00 am
TYS
- BOS
Nonstop2h 16m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Min 4/269:06 am
BOS
- TYS
Nonstop2h 29m
Multiple Airlines
Kam 4/3011:27 am
TYS
- BOS
1 stop20h 31m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Min 4/269:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Kam 4/306:00 am
TYS
- BOS
Nonstop2h 16m
Allegiant Air
Deal found 3/31![Allegiant Air logo]()
$181
This Expedia deal was found by Cheapflights users on 4/2. 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.
Kam 4/301:39 pm
BDL
- CVG
1 stop9h 41m
Multiple Airlines
Kam 5/78:40 pm
CVG
- BDL
Nonstop2h 02m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$137
This Super.com deal was found by Cheapflights users on 4/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sel 5/197:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Sel 5/198:40 pm
CVG
- BDL
Nonstop2h 02m
Breeze Airways
Deal found 4/2![Breeze Airways logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sab 5/239:45 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Sab 5/306:45 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 3/31![Allegiant Air logo]()
$151
This Breeze Airways deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Jum 5/297:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Jum 6/510:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 3/29![Breeze Airways logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sab 5/3010:46 am
BOS
- TYS
1 stop11h 32m
Allegiant Air
Min 5/317:30 am
TYS
- BOS
Nonstop2h 10m
Allegiant Air
Deal found 3/28![Allegiant Air logo]()
$141
One-way flights from Massachusetts to KentuckySearch for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
Search for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sab 4/259:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$46
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sen 6/19:21 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/1![Allegiant Air logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Jum 5/299:21 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/1![Allegiant Air logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Min 4/269:06 am
BOS
- TYS
Nonstop2h 29m
Allegiant Air
Deal found 3/30![Allegiant Air logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sen 6/299:13 pm
ALB
- BNA
Nonstop2h 19m
Allegiant Air
Deal found 4/1![Allegiant Air logo]()
$68
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” 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.
Sen 5/116:00 am
BOS
- CVG
1 stop5h 41m
Frontier
Deal found 3/30![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 4/2. 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.
Kam 4/231:33 pm
BDL
- CVG
1 stop9h 47m
Frontier
Deal found 4/2![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 3/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Rab 4/2911:16 am
BOS
- CVG
1 stop12h 04m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Min 5/177:00 am
BDL
- CVG
Nonstop2h 07m
Breeze Airways
Deal found 3/31![Breeze Airways logo]()
$78
This CheapOair deal was found by Cheapflights users on 4/1. 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.
Jum 5/18:42 pm
BDL
- BNA
1 stop21h 16m
Frontier
Deal found 4/1![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Sel 6/29:12 am
BOS
- CVG
1 stop26h 29m
Frontier
Deal found 4/1![Frontier logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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.
Sel 6/2311:38 am
BOS
- TYS
Nonstop2h 23m
Allegiant Air
Deal found 3/29![Allegiant Air logo]()
$83
Find flight deals from Massachusetts to Kentucky
Keep the following information in mind while searching for Massachusetts to Kentucky flight deals. Data was last updated April 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $85 (Cheapflightsfares) |
One-way from | $46 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $427 |
Good round-trip deal | $413 or less |
Good one-way deal | $288 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Kentucky 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 3, 2026.
Use the filters below to find and compare flights from Massachusetts to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
HartfordLouisville
BDL - SDF
BDLSDF
Hartford Bradley Intl
Jum 5/29
7:35 am-9:55 am
Nonstop2h 20m
Louisville Intl
Jum 6/5
10:35 am-12:45 pm
Nonstop2h 10m
$178
BostonKnoxville
BOS - TYS
BOSTYS
Boston Logan Intl
Sab 5/30
9:45 am-12:14 pm
Nonstop2h 29m
Knoxville McGhee Tyson
Min 5/31
8:15 am-11:06 am
2 stops26h 51m
$221
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Kam 5/7
7:20 pm-9:15 pm
Nonstop2h 55m
Nashville Intl
Sel 5/12
7:00 am-10:43 am
Nonstop2h 43m
$237
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Jum 5/8
2:55 pm-8:30 pm
2 stops6h 35m
Nashville Intl
Min 5/17
9:40 pm-8:00 am
1 stop9h 20m
$252
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Jum 5/1
8:10 pm-10:16 pm
Nonstop3h 06m
Nashville Intl
Jum 5/8
5:45 pm-9:30 pm
Nonstop2h 45m
$267
HartfordNashville
BDL - BNA
BDLBNA
Hartford Bradley Intl
Sab 6/13
4:50 pm-9:39 pm
1 stop5h 49m
Nashville Intl
Sab 6/20
6:00 am-2:24 pm
1 stop7h 24m
$268
AlbanyNashville
ALB - BNA
ALBBNA
Albany Intl
Jum 7/31
6:00 am-11:30 am
1 stop6h 30m
Nashville Intl
Sen 8/3
5:40 pm-11:06 pm
1 stop4h 26m
$270
BostonNashville
BOS - BNA
BOSBNA
Boston Logan Intl
Kam 6/4
1:00 pm-7:06 pm
1 stop7h 06m
Nashville Intl
Sab 6/6
7:05 am-10:48 am
Nonstop2h 43m
$272
HartfordNashville
BDL - BNA
BDLBNA
Hartford Bradley Intl
Sen 8/3
9:00 am-2:30 pm
2 stops6h 30m
Nashville Intl
Sen 8/10
5:40 am-12:00 pm
1 stop5h 20m
$273
BostonLexington
BOS - LEX
BOSLEX
Boston Logan Intl
Sel 6/2
3:00 pm-10:05 pm
1 stop7h 05m
Lexington Blue Grass
Sab 6/6
6:11 pm-1:28 am
1 stop7h 17m
$275
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Massachusetts with our price prediction graph.
BOS-TYS
ALB-BNA
BOS-CVG
BDL-CVG
BDL-BNA
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 Massachusetts to Kentucky
USMA-USKY
BOS-TYS
ALB-BNA
BOS-CVG
BDL-CVG
What is the cheapest month to book a flight from Massachusetts to Kentucky?
Currently, September is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $196). Flying from Massachusetts to Kentucky in March is currently the most expensive (average of $308). 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 MA to KY?
Find hourly flight availability from Massachusetts to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 3, 2026.
When flying from Massachusetts to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Massachusetts to Kentucky?
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated April 3, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Kentucky have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Kentucky. 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 Massachusetts to Kentucky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Kentucky by cabin class
Find flights from Massachusetts to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Kentucky flights
Browse other Massachusetts and Kentucky flight options. Last updated on April 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Kentucky
Find the right flight back to Massachusetts after your stay in Kentucky
Massachusetts to Kentucky flights
Consider these flights traveling from Massachusetts to Kentucky.
Top 4 airlines flying from Massachusetts to Kentucky
Discover the top 4 airlines that operate flights from Massachusetts to Kentucky. 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 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$439 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$387 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$407 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$318 | Average$402 | FlexibilityNo cancel fee | On-time63% |