$168+ Cheap flights from Massachusetts to Kentucky
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SDF
Dec 4 — Dec 111
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 November 4, 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 November 4, 2026.
This Delta deal was found by Cheapflights users on 11/1. 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.
Sun 11/226:45 am -
1 stop5h 04m
Thu 12/35:59 pm -
1 stop5h 59m
Deal found 11/1![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 11/247:31 am -
1 stop5h 42m
Tue 12/151:45 pm -
2 stops8h 14m
Deal found 11/2![United Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:45 am -
2 stops7h 17m
Wed 12/97:00 am -
2 stops7h 32m
Deal found 11/4![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/295:45 am -
1 stop7h 27m
Thu 1/78:40 am -
1 stop8h 19m
Deal found 11/1![United Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 10/31. 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.
Thu 11/195:30 am -
1 stop6h 19m
Sun 11/225:49 pm -
1 stop6h 05m
Deal found 10/31![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Thu 11/191:29 pm -
1 stop5h 41m
Sun 11/229:00 am -
2 stops7h 42m
Deal found 10/31![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 11/195:30 am -
1 stop6h 19m
Mon 11/237:35 am -
1 stop4h 18m
Deal found 11/3![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/295:29 pm -
1 stop6h 17m
Thu 1/711:55 am -
1 stop6h 50m
Deal found 11/4![American Airlines logo]()
$370
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 11/173:41 pm -
2 stops8h 13m
Sat 11/216:15 pm -
1 stop5h 43m
Deal found 11/2![United Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 11/123:01 pm -
1 stop5h 34m
Sun 11/155:25 am -
1 stop4h 54m
Deal found 11/1![United Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:25 am -
1 stop6h 01m
Mon 11/236:54 pm -
1 stop14h 45m
Deal found 11/4![Multiple Airlines logo]()
$453
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:20 am -
2 stops9h 20m
Thu 12/103:50 pm -
1 stop6h 25m
Deal found 11/2![Southwest logo]()
$454
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 November 4, 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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/4. 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 1/1511:52 am -
1 stop5h 30m
Sun 1/176:00 am -
1 stop7h 55m
Deal found 11/4![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/1. 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 11/1712:20 pm -
1 stop4h 47m
Wed 12/27:35 am -
1 stop4h 24m
Deal found 11/1![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 11/3. 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.
Wed 4/2811:30 am -
2 stops9h 25m
Sat 5/15:40 am -
1 stop6h 55m
Deal found 11/3![Southwest logo]()
$450
This United Airlines deal was found by Cheapflights users on 11/4. 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 1/149:09 am -
1 stop8h 13m
Sun 1/1710:50 am -
1 stop6h 09m
Deal found 11/4![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/1. 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 11/1910:10 am -
1 stop4h 43m
Thu 12/37:59 pm -
1 stop5h 11m
Deal found 11/1![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/295:45 am -
1 stop7h 27m
Thu 1/78:40 am -
1 stop8h 19m
Deal found 11/3![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 11/1. 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 11/175:30 am -
1 stop4h 23m
Tue 12/17:00 am -
1 stop5h 19m
Deal found 11/1![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 11/191:29 pm -
1 stop5h 41m
Wed 12/21:45 pm -
1 stop8h 08m
Deal found 11/1![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 11/2. 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 1/152:25 pm -
2 stops9h 30m
Mon 1/187:00 am -
2 stops7h 20m
Deal found 11/2![Southwest logo]()
$460
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Thu 11/191:29 pm -
1 stop5h 41m
Sun 11/229:00 am -
2 stops7h 42m
Deal found 10/31![United Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 11/4. 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 12/225:15 am -
1 stop10h 20m
Mon 12/282:10 pm -
2 stops7h 10m
Deal found 11/4![Southwest logo]()
$475
This Delta deal was found by Cheapflights users on 10/31. 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.
Sat 12/511:45 am -
Nonstop2h 52m
Sun 12/61:39 pm -
Nonstop2h 21m
Deal found 10/31![Delta logo]()
$464
This Southwest deal was found by Cheapflights users on 11/1. 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.
Tue 12/225:25 am -
2 stops10h 10m
Sun 12/275:40 am -
1 stop4h 00m
Deal found 11/1![Southwest logo]()
$489
This Delta deal was found by Cheapflights users on 11/1. 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 3/179:30 am -
Nonstop2h 48m
Sun 3/216:05 am -
1 stop6h 16m
Deal found 11/1![Delta logo]()
$474
This Southwest deal was found by Cheapflights users on 11/2. 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 12/2310:25 pm -
1 stop12h 05m
Mon 12/285:40 am -
1 stop4h 00m
Deal found 11/2![Southwest logo]()
$489
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/14:45 pm -
1 stop7h 09m
Tue 12/82:40 pm -
1 stop6h 13m
Deal found 10/31![United Airlines logo]()
$460
This Delta deal was found by Cheapflights users on 11/1. 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 3/189:30 am -
Nonstop2h 48m
Mon 3/221:00 pm -
Nonstop2h 30m
Deal found 11/1![Delta logo]()
$503
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/14:45 pm -
1 stop7h 09m
Sun 12/68:45 am -
2 stops12h 14m
Deal found 10/31![United Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 11/3. 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.
Wed 4/216:00 am -
1 stop5h 03m
Sun 4/256:05 am -
1 stop6h 16m
Deal found 11/3![Delta logo]()
$512
This Delta deal was found by Cheapflights users on 11/4. 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.
Sun 4/49:30 am -
Nonstop2h 48m
Sun 4/116:05 am -
1 stop7h 16m
Deal found 11/4![Delta logo]()
$523
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/235:00 pm -
2 stops21h 38m
Sat 1/29:00 am -
1 stop4h 25m
Deal found 11/1![United Airlines logo]()
$528
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Tue 12/112:00 pm -
2 stops11h 54m
Sat 12/52:40 pm -
2 stops8h 19m
Deal found 10/31![United Airlines logo]()
$568
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Mon 11/306:36 pm -
1 stop5h 29m
Mon 12/78:45 am -
1 stop4h 47m
Deal found 10/31![United Airlines logo]()
$575
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/225:45 am -
1 stop8h 58m
Mon 12/285:00 am -
1 stop19h 18m
Deal found 11/1![United Airlines logo]()
$724
This United Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/224:29 pm -
1 stop7h 30m
Sat 12/262:13 pm -
1 stop6h 46m
Deal found 11/3![United Airlines logo]()
$736
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Mon 11/165:30 am -
2 stops9h 11m
Fri 11/205:30 am -
2 stops28h 21m
Deal found 11/1![United Airlines logo]()
$743
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Sun 11/294:56 pm -
1 stop7h 09m
Fri 12/42:40 pm -
2 stops8h 19m
Deal found 10/31![United Airlines logo]()
$829
Last-minute flights from Massachusetts to KentuckyDiscover last-minute flight deals from Massachusetts to Kentucky. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Kentucky. Data last updated November 4, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/1. 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.
Thu 11/123:01 pm -
1 stop5h 34m
Sun 11/155:25 am -
1 stop4h 54m
Deal found 11/1![United Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 11/173:41 pm -
2 stops8h 13m
Sat 11/216:15 pm -
1 stop5h 43m
Deal found 11/2![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 10/31. 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.
Thu 11/198:00 am -
1 stop6h 53m
Sun 11/225:49 pm -
1 stop6h 05m
Deal found 10/31![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/31. 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.
Thu 11/191:29 pm -
1 stop5h 41m
Sun 11/229:00 am -
2 stops7h 42m
Deal found 10/31![United Airlines logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:25 am -
1 stop6h 01m
Mon 11/236:54 pm -
1 stop14h 45m
Deal found 11/4![Multiple Airlines logo]()
$453
This Delta deal was found by Cheapflights users on 11/1. 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.
Sun 11/226:45 am -
1 stop5h 04m
Thu 12/35:59 pm -
1 stop5h 59m
Deal found 11/1![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 11/247:31 am -
1 stop5h 42m
Tue 12/151:45 pm -
2 stops8h 14m
Deal found 11/2![United Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:45 am -
2 stops7h 17m
Wed 12/97:00 am -
2 stops7h 32m
Deal found 11/4![United Airlines logo]()
$349
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:20 am -
2 stops9h 20m
Thu 12/103:50 pm -
1 stop6h 25m
Deal found 11/2![Southwest logo]()
$454
This Southwest deal was found by Cheapflights users on 11/1. 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.
Tue 12/225:15 am -
1 stop10h 20m
Mon 12/285:35 pm -
1 stop3h 45m
Deal found 11/1![Southwest logo]()
$455
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/295:45 am -
1 stop7h 27m
Thu 1/78:40 am -
1 stop8h 19m
Deal found 11/1![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/295:29 pm -
1 stop6h 17m
Thu 1/711:55 am -
1 stop6h 50m
Deal found 11/4![American Airlines logo]()
$370
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 November 4, 2026.
Search for one-way flight options from Massachusetts to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1310:31 am -
1 stop25h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Allegiant Air logo]()
$168
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:18 am -
1 stop8h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
Sun 1/1710:29 am -
1 stop23h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Allegiant Air logo]()
$188
This Southwest deal was found by Cheapflights users on 11/1. 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.
Mon 11/235:35 am -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 11/2. 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.
Mon 12/71:10 pm -
2 stops7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 11/2. 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 12/15:30 am -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Southwest logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/411:08 am -
2 stops29h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/1712:15 pm -
2 stops27h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 4/2912:02 pm -
2 stops28h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$226
This Southwest deal was found by Cheapflights users on 11/1. 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.
Tue 11/245:25 am -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Southwest logo]()
$227
This KAYAK deal was found by Cheapflights users on 11/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:29 pm -
1 stop8h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Delta logo]()
$270
This Delta deal was found by Cheapflights users on 11/3. 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 12/184:59 pm -
1 stop4h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$284
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (Delta) |
One-way from | $168 (Kiwi.com) |
Popular in | October |
Cheapest in | February |
Average price | $480 |
Good round-trip deal | $483 or less |
Good one-way deal | $368 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 7,457,451 searches. Data last updated November 4, 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
BostonLexington
BOS Boston Logan Intl - LEX Lexington Blue Grass
BOSLEX
Boston Logan Intl
Thu 11/26
8:18 am-5:09 pm
1 stop8h 51m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$170
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Mon 11/23
5:35 am-12:30 pm
1 stop6h 55m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Fri 12/4
3:30 pm-10:15 pm
1 stop6h 45m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Tue 12/1
5:10 am-1:00 pm
2 stops7h 50m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Tue 11/24
5:25 am-12:25 pm
1 stop7h 00m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Sun 1/17
9:20 am-7:50 pm
2 stops10h 30m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Fri 12/4
11:58 am-4:32 pm
3 stops28h 34m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$243
BostonLexington
BOS Boston Logan Intl - LEX Lexington Blue Grass
BOSLEX
Boston Logan Intl
Tue 12/8
2:29 pm-11:23 pm
1 stop8h 54m
Lexington Blue Grass
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$270
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Tue 11/17
5:30 am-1:00 pm
1 stop7h 30m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
BostonLouisville
BOS Boston Logan Intl - SDF Louisville Intl
BOSSDF
Boston Logan Intl
Wed 11/11
1:10 pm-8:40 pm
2 stops7h 30m
Louisville Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
Showing 1-10 of 49 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-LEX
BOS-SDF
BOS-OWB
BOS-PAH
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-LEX
BOS-SDF
BOS-OWB
BOS-PAH
What is the cheapest month to book a flight from Massachusetts to Kentucky?
Currently, February is the cheapest month in which you can book a flight from Massachusetts to Kentucky (average of $397). Flying from Massachusetts to Kentucky in October is currently the most expensive (average of $558). 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 November 4, 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.
Weekly flight availability from Massachusetts to Kentucky
Explore weekly flight availability from Massachusetts to Kentucky. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 4, 2026.
The most flights from USMA to USKY are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Massachusetts to Kentucky?
Airfare is typical for this route at the moment.
Massachusetts to Kentucky flights typically cost between $444 and $575 in March.The cheapest round-trip price found within the last 5 days was $450 on Southwest (Mar 31-Apr 7).
How far ahead should I book a flight from Massachusetts to Kentucky?
The best time to book flights from Massachusetts to Kentucky is 78 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 November 4, 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.
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 November 4, 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 5 airlines flying from Massachusetts to Kentucky
Discover the top 5 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$458 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$269 | Average$458 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$342 | Average$522 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$353 | Average$508 | FlexibilityNo cancel fee | On-time69% |