$150+ Cheap flights from Portland (PDX) 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SDF
Nov 11 — Nov 181
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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
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Cheapest flights from Portland to KentuckyExplore the most affordable flight options available from Portland to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 12, 2026.
Explore the most affordable flight options available from Portland to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 12, 2026.
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/45:00 am -
1 stop6h 22m
Mon 11/92:11 pm -
1 stop9h 04m
Deal found 10/7![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/45:00 am -
1 stop6h 22m
Wed 11/1110:37 am -
2 stops10h 32m
Deal found 10/7![United Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/185:00 am -
1 stop6h 22m
Sun 11/223:24 pm -
1 stop8h 49m
Deal found 10/7![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/410:15 am -
2 stops9h 40m
Mon 11/94:05 pm -
2 stops11h 10m
Deal found 10/7![Southwest logo]()
$351
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/192:34 pm -
1 stop6h 41m
Sun 11/226:48 pm -
1 stop8h 28m
Deal found 10/8![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/1011:59 am -
1 stop7h 47m
Sat 11/145:40 pm -
1 stop7h 30m
Deal found 10/9![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/611:30 pm -
1 stop7h 45m
Mon 11/94:05 pm -
2 stops11h 10m
Deal found 10/9![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/310:15 am -
2 stops9h 40m
Mon 12/77:20 am -
2 stops8h 50m
Deal found 10/12![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Sun 12/209:05 pm -
2 stops9h 55m
Mon 1/44:40 pm -
2 stops10h 30m
Deal found 10/10![Southwest logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/107:00 am -
1 stop9h 10m
Tue 11/1711:05 am -
1 stop7h 18m
Deal found 10/11![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/292:20 pm -
1 stop6h 39m
Tue 11/36:00 am -
1 stop7h 42m
Deal found 10/11![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/2911:30 pm -
1 stop7h 43m
Tue 11/311:05 am -
2 stops10h 15m
Deal found 10/11![United Airlines logo]()
$444
Best flights from Portland to KentuckyDiscover carefully curated flight deals from Portland to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 12, 2026.
Discover carefully curated flight deals from Portland to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 12, 2026.
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/1011:59 am -
1 stop7h 47m
Sat 11/145:40 pm -
1 stop7h 30m
Deal found 10/11![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/78:30 am -
1 stop6h 25m
Mon 11/94:05 pm -
2 stops11h 10m
Deal found 10/9![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/107:00 am -
1 stop9h 10m
Tue 11/1711:05 am -
1 stop7h 18m
Deal found 10/11![United Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/281:12 pm -
1 stop7h 57m
Mon 11/23:54 pm -
1 stop10h 49m
Deal found 10/8![American Airlines logo]()
$646
This Southwest deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/310:15 am -
2 stops9h 40m
Mon 12/77:20 am -
2 stops8h 50m
Deal found 10/12![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 12/127:33 pm -
2 stops10h 57m
Wed 12/1610:50 am -
1 stop7h 29m
Deal found 10/8![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/411:25 am -
2 stops8h 30m
Wed 11/117:20 am -
2 stops8h 50m
Deal found 10/7![Southwest logo]()
$393
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/292:20 pm -
1 stop6h 39m
Tue 11/36:00 am -
1 stop7h 42m
Deal found 10/11![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 12/55:00 am -
1 stop6h 17m
Wed 12/93:20 pm -
1 stop8h 55m
Deal found 10/7![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/3011:51 am -
1 stop8h 00m
Sun 11/16:39 pm -
1 stop8h 05m
Deal found 10/7![Delta logo]()
$455
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Sun 12/2011:30 pm -
1 stop7h 30m
Mon 1/41:05 pm -
1 stop10h 15m
Deal found 10/10![Southwest logo]()
$420
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/2911:30 pm -
1 stop7h 43m
Tue 11/311:05 am -
2 stops10h 15m
Deal found 10/11![United Airlines logo]()
$444
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/69:00 pm -
2 stops10h 15m
Mon 11/94:05 pm -
2 stops11h 10m
Deal found 10/9![Southwest logo]()
$435
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 10/232:20 pm -
1 stop6h 39m
Mon 10/265:38 pm -
1 stop7h 24m
Deal found 10/8![Delta logo]()
$495
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 12/221:25 pm -
1 stop7h 40m
Fri 12/258:50 am -
1 stop6h 45m
Deal found 10/9![Southwest logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 12/128:50 am -
2 stops10h 42m
Thu 12/1710:08 am -
1 stop8h 18m
Deal found 10/8![United Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/511:00 pm -
1 stop7h 25m
Sun 11/85:53 pm -
1 stop7h 09m
Deal found 10/9![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/82:20 pm -
1 stop6h 38m
Sun 11/156:00 am -
1 stop7h 41m
Deal found 10/9![Delta logo]()
$559
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 10/2211:30 pm -
1 stop6h 58m
Mon 10/2611:05 am -
2 stops10h 19m
Deal found 10/7![United Airlines logo]()
$583
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/85:00 am -
2 stops9h 30m
Sun 11/157:10 am -
1 stop7h 37m
Deal found 10/9![United Airlines logo]()
$660
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 10/289:00 am -
2 stops11h 54m
Mon 11/29:00 am -
2 stops14h 15m
Deal found 10/9![United Airlines logo]()
$668
Last-minute flights from Portland to KentuckyDiscover last-minute flight deals from Portland to Kentucky. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Kentucky. Data last updated October 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/292:20 pm -
1 stop6h 39m
Tue 11/36:00 am -
1 stop7h 42m
Deal found 10/11![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 10/2911:30 pm -
1 stop7h 43m
Tue 11/311:05 am -
2 stops10h 15m
Deal found 10/11![United Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/45:00 am -
1 stop6h 22m
Mon 11/92:11 pm -
1 stop9h 04m
Deal found 10/7![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/45:00 am -
1 stop6h 22m
Wed 11/1110:37 am -
2 stops10h 32m
Deal found 10/7![United Airlines logo]()
$304
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/410:15 am -
2 stops9h 40m
Mon 11/94:05 pm -
2 stops11h 10m
Deal found 10/7![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/411:25 am -
2 stops8h 30m
Wed 11/117:20 am -
2 stops8h 50m
Deal found 10/7![Southwest logo]()
$393
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/611:30 pm -
1 stop7h 45m
Mon 11/94:05 pm -
2 stops11h 10m
Deal found 10/9![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” 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 11/1011:59 am -
1 stop7h 47m
Sat 11/145:40 pm -
1 stop7h 30m
Deal found 10/9![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/107:00 am -
1 stop9h 10m
Tue 11/1711:05 am -
1 stop7h 18m
Deal found 10/11![United Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/185:00 am -
1 stop6h 22m
Sun 11/223:24 pm -
1 stop8h 49m
Deal found 10/7![United Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” 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 11/1810:15 am -
2 stops9h 40m
Sun 11/225:35 pm -
2 stops10h 50m
Deal found 10/7![Southwest logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/192:34 pm -
1 stop6h 41m
Sun 11/226:48 pm -
1 stop8h 28m
Deal found 10/8![American Airlines logo]()
$360
One-way flights from Portland to KentuckySearch for one-way flight options from Portland to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
Search for one-way flight options from Portland to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 12, 2026.
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/411:09 pm -
1 stop7h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/312:02 pm -
3 stops24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$169
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 11/47:00 am -
1 stop8h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![United Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 1/67:00 am -
2 stops12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/611:00 pm -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$192
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/46:00 am -
1 stop8h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Delta logo]()
$200
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 11/811:10 pm -
1 stop10h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![United Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/69:00 pm -
2 stops10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/812:31 pm -
2 stops27h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 1/54:29 pm -
3 stops43h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” 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 11/611:06 am -
3 stops41h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 1/67:10 am -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![United Airlines logo]()
$389
Find flight deals from Portland to Kentucky
Keep the following information in mind while searching for Portland to Kentucky flight deals. Data was last updated October 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (United Airlines) |
One-way from | $150 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $414 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 October 12, 2026.
Use the filters below to find and compare flights from Portland to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Tue 11/3
11:43 am-9:13 pm
1 stop6h 30m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$150
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Thu 11/12
2:24 pm-12:10 am
1 stop6h 46m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$150
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Wed 11/4
11:09 pm-9:38 am
1 stop7h 29m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Fri 11/6
11:00 pm-10:21 am
1 stop8h 21m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$192
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Fri 1/1
6:00 am-3:35 pm
1 stop6h 35m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Wed 11/4
5:00 am-2:22 pm
1 stop6h 22m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$210
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Thu 11/12
8:30 am-10:30 pm
2 stops11h 00m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$215
Quickest round-trip
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Mon 1/4
6:15 am-3:17 pm
1 stop6h 02m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Sun 11/8
11:00 pm-9:06 am
1 stop7h 06m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$234
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Sun 11/15
5:00 am-3:30 pm
1 stop7h 30m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$240
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Portland to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Portland with our price prediction graph.
PDX-SDF
PDX-LEX
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 Portland to Kentucky
PDX-USKY
PDX-SDF
PDX-LEX
What is the cheapest month to book a flight from Portland to Kentucky?
Currently, January is the cheapest month in which you can book a flight from Portland to Kentucky (average of $428). Flying from Portland to Kentucky in June is currently the most expensive (average of $557). 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.
How much does it cost to fly round-trip from Portland to Kentucky?
Airfare is below average for this route at the moment.
Portland to Kentucky flights typically cost between $376 and $536 in November.The cheapest round-trip price found within the last 5 days was $299 on United Airlines (Nov 4-Nov 9).
How far ahead should I book a flight from Portland to Kentucky?
Booking 70 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Kentucky. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 October 12, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Portland to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Portland to Kentucky
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Complete your trip
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Search flights from Portland to Kentucky by cabin class
Find flights from Portland to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Kentucky flights
Browse other Portland and Kentucky flight options. Last updated on October 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Kentucky flights
Consider these flights traveling from Portland to Kentucky.
Top 4 airlines flying from Portland to Kentucky
Discover the top 4 airlines that operate flights from Portland 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 October 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$292 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$339 | Average$497 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$341 | Average$511 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$354 | Average$496 | FlexibilityNo cancel fee | On-time63% |