$157+ Cheap flights from Kentucky to Boston (BOS)
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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — BOS
Nov 1 — Nov 81
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Boston 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
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Cheapest flights from Kentucky to BostonExplore the most affordable flight options available from Kentucky to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2026.
Explore the most affordable flight options available from Kentucky to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2026.
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop8h 51m
Wed 11/412:39 pm -
1 stop8h 48m
Deal found 9/30![American Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am -
1 stop8h 51m
Tue 11/38:16 am -
1 stop9h 27m
Deal found 9/29![American Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Fri 11/138:54 pm -
1 stop12h 35m
Sat 11/219:25 am -
1 stop6h 01m
Deal found 9/30![Multiple Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:22 pm -
Nonstop2h 31m
Sun 11/19:00 am -
Nonstop2h 30m
Deal found 9/30![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/1. 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 10/295:58 pm -
1 stop6h 01m
Thu 11/59:00 am -
1 stop5h 42m
Deal found 10/1![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/1. 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 10/297:59 pm -
1 stop5h 21m
Sun 11/15:39 am -
1 stop5h 12m
Deal found 10/1![Delta logo]()
$340
This Delta deal was found by Cheapflights users on 9/30. 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.
Wed 10/2810:39 am -
2 stops13h 03m
Wed 11/412:20 pm -
2 stops10h 27m
Deal found 9/30![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Thu 10/295:30 am -
1 stop4h 48m
Tue 11/312:00 pm -
2 stops8h 35m
Deal found 9/28![United Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Sun 10/258:42 pm -
1 stop15h 27m
Tue 10/2711:12 am -
2 stops22h 59m
Deal found 9/30![Multiple Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am -
1 stop8h 51m
Sat 10/3111:18 am -
Nonstop2h 42m
Deal found 9/30![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/168:45 am -
1 stop7h 14m
Tue 10/209:30 am -
1 stop5h 10m
Deal found 10/1![United Airlines logo]()
$390
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/165:00 am -
2 stops10h 59m
Sun 10/185:45 am -
2 stops8h 47m
Deal found 10/1![United Airlines logo]()
$399
Best flights from Kentucky to BostonDiscover carefully curated flight deals from Kentucky to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2026.
Discover carefully curated flight deals from Kentucky to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2026.
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:59 pm -
1 stop5h 15m
Tue 11/310:00 am -
1 stop4h 42m
Deal found 9/28![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Mon 11/25:25 am -
1 stop4h 53m
Mon 11/912:00 pm -
2 stops8h 35m
Deal found 10/2![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/195:40 am -
1 stop6h 55m
Tue 12/295:25 am -
1 stop7h 00m
Deal found 9/27![Southwest logo]()
$441
This Delta deal was found by Cheapflights users on 10/1. 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 12/37:05 am -
1 stop5h 33m
Sun 12/66:20 am -
1 stop5h 27m
Deal found 10/1![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Thu 10/295:30 am -
1 stop4h 48m
Tue 11/312:00 pm -
2 stops8h 35m
Deal found 9/28![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:59 pm -
1 stop5h 16m
Mon 12/75:27 am -
1 stop4h 33m
Deal found 10/2![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/2. 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 12/35:00 am -
1 stop5h 31m
Mon 12/72:36 pm -
2 stops7h 56m
Deal found 10/2![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 10/1. 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 10/297:59 pm -
1 stop5h 21m
Sun 11/15:39 am -
1 stop5h 12m
Deal found 10/1![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Sat 10/1710:11 am -
2 stops9h 14m
Sat 10/247:55 am -
1 stop5h 26m
Deal found 9/29![United Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 10/1. 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 11/198:50 am -
2 stops8h 00m
Tue 11/247:00 am -
1 stop6h 35m
Deal found 10/1![Southwest logo]()
$459
This Delta deal was found by Cheapflights users on 9/29. 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.
Sat 10/171:53 pm -
1 stop5h 29m
Sat 10/245:39 am -
1 stop4h 09m
Deal found 9/29![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 10/2. 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 10/303:35 pm -
2 stops8h 35m
Fri 11/67:45 pm -
1 stop4h 40m
Deal found 10/2![Southwest logo]()
$462
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Thu 10/226:00 am -
1 stop5h 01m
Sat 11/76:00 am -
1 stop7h 13m
Deal found 9/28![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/2. 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.
Mon 12/143:34 pm -
1 stop7h 46m
Sat 1/24:52 pm -
1 stop4h 25m
Deal found 10/2![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 9/30. 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.
Sat 10/317:00 am -
2 stops8h 55m
Mon 11/23:30 pm -
2 stops8h 50m
Deal found 9/30![Southwest logo]()
$474
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/165:00 am -
2 stops10h 59m
Sun 10/185:45 am -
2 stops8h 47m
Deal found 10/1![United Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Fri 11/65:25 am -
2 stops8h 06m
Mon 11/96:36 pm -
1 stop5h 18m
Deal found 9/29![United Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/301:20 pm -
Nonstop2h 37m
Tue 11/39:45 am -
Nonstop2h 42m
Deal found 9/27![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/135:15 pm -
1 stop5h 44m
Sat 10/179:30 am -
1 stop5h 10m
Deal found 9/28![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/221:30 pm -
Nonstop2h 31m
Tue 12/19:55 am -
Nonstop2h 54m
Deal found 9/28![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:25 pm -
1 stop8h 04m
Wed 11/49:30 am -
1 stop5h 10m
Deal found 9/28![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/316:00 am -
1 stop5h 02m
Sun 4/49:30 am -
Nonstop2h 48m
Deal found 9/27![Delta logo]()
$454
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 12/42:40 pm -
1 stop6h 13m
Mon 12/79:30 am -
1 stop5h 35m
Deal found 10/2![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 10/2. 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.
Mon 11/233:14 pm -
1 stop4h 35m
Tue 12/18:00 am -
1 stop6h 16m
Deal found 10/2![Delta logo]()
$464
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:45 am -
1 stop4h 47m
Wed 11/46:36 pm -
1 stop5h 29m
Deal found 10/1![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 9/30. 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.
Tue 10/201:20 pm -
Nonstop2h 37m
Sun 11/112:15 pm -
Nonstop2h 40m
Deal found 9/30![Delta logo]()
$495
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sun 1/178:45 am -
2 stops7h 39m
Sat 1/234:54 pm -
1 stop7h 01m
Deal found 10/1![United Airlines logo]()
$460
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/135:15 pm -
1 stop5h 44m
Tue 10/209:30 am -
1 stop5h 10m
Deal found 9/28![United Airlines logo]()
$475
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Tue 10/135:00 am -
1 stop5h 01m
Sat 10/177:01 am -
1 stop7h 31m
Deal found 9/28![United Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Fri 10/165:00 am -
2 stops10h 59m
Mon 10/198:05 am -
1 stop6h 27m
Deal found 10/2![United Airlines logo]()
$504
Last-minute flights from Kentucky to BostonDiscover last-minute flight deals from Kentucky to Boston. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Boston. Data last updated October 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/168:45 am -
1 stop7h 14m
Tue 10/209:30 am -
1 stop5h 10m
Deal found 10/1![United Airlines logo]()
$390
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Fri 10/165:00 am -
2 stops10h 59m
Sun 10/185:45 am -
2 stops8h 47m
Deal found 10/1![United Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Sun 10/258:42 pm -
1 stop15h 27m
Tue 10/2711:12 am -
2 stops22h 59m
Deal found 9/30![Multiple Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am -
1 stop8h 51m
Tue 11/38:16 am -
1 stop9h 27m
Deal found 9/29![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am -
1 stop8h 51m
Sat 10/3111:18 am -
Nonstop2h 42m
Deal found 9/30![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop8h 51m
Wed 11/412:39 pm -
1 stop8h 48m
Deal found 9/30![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 9/30. 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.
Wed 10/2810:39 am -
2 stops13h 03m
Wed 11/412:20 pm -
2 stops10h 27m
Deal found 9/30![Delta logo]()
$343
This American Airlines deal was found by Cheapflights users on 9/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:22 pm -
Nonstop2h 31m
Sun 11/19:00 am -
Nonstop2h 30m
Deal found 9/30![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/1. 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 10/295:58 pm -
1 stop6h 01m
Thu 11/59:00 am -
1 stop5h 42m
Deal found 10/1![Delta logo]()
$339
This Delta deal was found by Cheapflights users on 10/1. 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 10/297:59 pm -
1 stop5h 21m
Sun 11/15:39 am -
1 stop5h 12m
Deal found 10/1![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 9/28. 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.
Thu 10/295:30 am -
1 stop4h 48m
Tue 11/312:00 pm -
2 stops8h 35m
Deal found 9/28![United Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Fri 11/138:54 pm -
1 stop12h 35m
Sat 11/219:25 am -
1 stop6h 01m
Deal found 9/30![Multiple Airlines logo]()
$315
One-way flights from Kentucky to BostonSearch for one-way flight options from Kentucky to Boston. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
Search for one-way flight options from Kentucky to Boston. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:42 pm -
1 stop15h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Allegiant Air logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Fri 10/308:10 pm -
1 stop13h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Allegiant Air logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Sun 11/17:42 pm -
1 stop16h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Allegiant Air logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Thu 10/298:34 pm -
1 stop13h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Allegiant Air logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Fri 10/169:14 pm -
1 stop12h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Allegiant Air logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Thu 10/229:09 pm -
2 stops36h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
Mon 11/27:08 pm -
3 stops40h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$183
This Southwest deal was found by Cheapflights users on 9/29. 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.
Tue 10/273:55 pm -
1 stop5h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Southwest logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Wed 10/2110:55 am -
2 stops24h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Fri 10/309:18 pm -
2 stops37h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Allegiant Air logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Thu 10/298:51 pm -
2 stops35h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Allegiant Air logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Tue 10/2711:20 am -
2 stops44h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Allegiant Air logo]()
$249
Find flight deals from Kentucky to Boston
Keep the following information in mind while searching for Kentucky to Boston flight deals. Data was last updated October 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $310 (American Airlines) |
One-way from | $157 (Kiwi.com) |
Popular in | April |
Cheapest in | December |
Average price | $421 |
Good round-trip deal | $487 or less |
Good one-way deal | $348 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Boston 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 October 2, 2026.
Use the filters below to find and compare flights from Kentucky to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 10/28
3:55 pm-10:45 pm
1 stop6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Fri 11/27
7:00 am-2:30 pm
2 stops7h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$234
LouisvilleBoston
SDF Louisville Intl - BOS Boston Logan Intl
SDFBOS
Louisville Intl
Wed 10/7
3:55 pm-9:20 pm
1 stop5h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$264
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Mon 12/28
5:50 pm-1:18 am
1 stop7h 28m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Mon 1/4
5:05 am-12:51 pm
1 stop7h 46m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Mon 11/2
5:53 pm-11:59 pm
1 stop6h 06m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Thu 10/29
12:28 pm-5:30 pm
1 stop5h 02m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Tue 12/29
5:50 pm-1:18 am
1 stop7h 28m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Tue 10/27
7:10 am-1:59 pm
1 stop6h 49m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
LexingtonBoston
LEX Lexington Blue Grass - BOS Boston Logan Intl
LEXBOS
Lexington Blue Grass
Sun 11/1
7:59 pm-1:20 am
1 stop5h 21m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$284
Showing 1-10 of 53 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Kentucky with our price prediction graph.
SDF-BOS
LEX-BOS
OWB-BOS
PAH-BOS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Boston
USKY-BOS
SDF-BOS
LEX-BOS
OWB-BOS
PAH-BOS
What is the cheapest month to book a flight from Kentucky to Boston?
Currently, January is the cheapest month in which you can book a flight from Kentucky to Boston (average of $354). Flying from Kentucky to Boston in April is currently the most expensive (average of $488). 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 BOS?
Find hourly flight availability from Kentucky to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 2, 2026.
It’s typically best to fly out from Kentucky to Boston at noon. Doing so could potentially save you 77% on the flight price compared to flying in the evening, which is usually more expensive.
How much does it cost to fly round-trip from Kentucky to Boston?
Airfare is below average for this route at the moment.
Kentucky to Boston flights typically cost between $364 and $548 in October.The cheapest round-trip price found within the last 5 days was $310 on American Airlines (Oct 28-Nov 4).
How far ahead should I book a flight from Kentucky to Boston?
Booking 74 days in advance of your planned departure date is, on average, the best time to get cheap flights from Kentucky to Boston. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Revere
Warwick
Pawtucket
Peabody
Auburn
Londonderry
York Beach
Fitchburg
North Falmouth
Swansea
Chelsea
Braintree
Sandwich
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
Boston flight routes
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Alternative routes for Kentucky to Boston
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 2, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Boston by cabin class
Find flights from Kentucky to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Boston flights
Browse other Kentucky and Boston flight options. Last updated on October 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Kentucky to Boston flights
Consider these flights traveling from Kentucky to Boston.
Top 4 airlines flying from Kentucky to Boston
Discover the top 4 airlines that operate flights from Kentucky to Boston. 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 October 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$411 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$411 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$275 | Average$415 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$294 | Average$437 | FlexibilityNo cancel fee | On-time69% |