$156+ Cheap flights from Oregon 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SDF
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Oregon 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 Oregon to KentuckyExplore the most affordable flight options available from Oregon to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Oregon to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/30. 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.
Thu 12/36:55 am -
1 stop7h 15m
Mon 12/77:35 pm -
1 stop6h 50m
Deal found 10/30![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/31:50 pm -
1 stop6h 05m
Tue 12/83:10 pm -
2 stops10h 10m
Deal found 10/26![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1711:51 am -
1 stop6h 51m
Fri 11/206:55 pm -
1 stop7h 51m
Deal found 10/26![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 12/26:30 am -
1 stop9h 25m
Mon 12/77:20 am -
2 stops8h 50m
Deal found 10/27![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 11/1812:35 am -
1 stop8h 25m
Sun 11/226:00 am -
1 stop7h 41m
Deal found 10/29![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:26 pm -
1 stop6h 23m
Sat 12/127:10 am -
2 stops10h 28m
Deal found 10/30![United Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/2411:51 am -
1 stop8h 22m
Thu 12/36:35 am -
1 stop7h 13m
Deal found 10/28![Delta logo]()
$375
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:49 pm -
1 stop7h 33m
Fri 11/201:14 pm -
1 stop10h 15m
Deal found 10/25![American Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 11/235:00 am -
1 stop6h 22m
Wed 12/23:20 pm -
1 stop9h 17m
Deal found 10/29![United Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/1910:15 am -
2 stops9h 40m
Sat 11/218:30 pm -
1 stop7h 55m
Deal found 10/29![Southwest logo]()
$380
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/258:46 am -
2 stops10h 53m
Thu 1/72:05 pm -
1 stop7h 54m
Deal found 10/28![United Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 11/247:25 pm -
2 stops11h 13m
Thu 12/33:20 pm -
1 stop9h 17m
Deal found 10/29![United Airlines logo]()
$384
Best flights from Oregon to KentuckyDiscover carefully curated flight deals from Oregon to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Oregon to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/29. 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 2/236:55 am -
2 stops10h 20m
Fri 2/268:15 pm -
1 stop6h 55m
Deal found 10/29![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 1/1910:33 pm -
1 stop8h 03m
Fri 1/226:25 am -
1 stop9h 05m
Deal found 10/29![Delta logo]()
$377
This United Airlines deal was found by Cheapflights users on 10/28. 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 4/205:10 am -
1 stop6h 17m
Mon 4/263:20 pm -
1 stop8h 50m
Deal found 10/28![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:46 pm -
2 stops13h 13m
Sat 11/145:14 am -
2 stops12h 22m
Deal found 10/26![Alaska Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/257:07 am -
2 stops12h 23m
Wed 12/23:20 pm -
1 stop9h 17m
Deal found 10/28![United Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 10/28. 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 11/276:20 am -
2 stops11h 53m
Wed 12/27:05 am -
2 stops14h 55m
Deal found 10/28![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 11/235:00 am -
1 stop6h 22m
Wed 12/29:00 am -
2 stops12h 27m
Deal found 10/29![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sun 12/201:25 pm -
1 stop7h 45m
Mon 1/410:45 am -
2 stops15h 45m
Deal found 10/29![Southwest logo]()
$423
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 11/247:27 pm -
2 stops13h 33m
Wed 12/23:12 pm -
2 stops10h 49m
Deal found 10/29![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 11/247:25 pm -
2 stops11h 13m
Wed 12/23:20 pm -
1 stop9h 17m
Deal found 10/29![United Airlines logo]()
$384
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/179:00 pm -
2 stops10h 00m
Sun 12/2010:40 am -
2 stops11h 55m
Deal found 10/25![Southwest logo]()
$442
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 1/1412:47 pm -
1 stop8h 08m
Wed 1/203:59 pm -
1 stop9h 03m
Deal found 10/28![Delta logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am -
1 stop7h 15m
Sat 12/1210:50 am -
1 stop7h 29m
Deal found 10/27![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 10/30. 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.
Thu 12/174:41 pm -
2 stops13h 27m
Sun 12/2011:27 am -
2 stops15h 32m
Deal found 10/30![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2911:30 pm -
1 stop7h 30m
Fri 1/17:20 am -
2 stops8h 50m
Deal found 10/28![Southwest logo]()
$478
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/2511:30 pm -
1 stop7h 14m
Thu 12/37:10 am -
2 stops10h 28m
Deal found 10/28![United Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 10/28. 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 11/1511:10 pm -
1 stop7h 28m
Sat 11/215:49 pm -
1 stop7h 21m
Deal found 10/28![Delta logo]()
$439
This Southwest deal was found by Cheapflights users on 10/30. 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.
Thu 12/175:15 am -
2 stops11h 00m
Sun 12/207:05 am -
1 stop9h 45m
Deal found 10/30![Southwest logo]()
$483
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/237:10 am -
1 stop7h 10m
Sat 1/3010:50 am -
2 stops12h 55m
Deal found 10/27![United Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/305:00 am -
2 stops9h 20m
Sat 2/66:00 am -
2 stops11h 36m
Deal found 10/27![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 4/88:15 pm -
2 stops11h 00m
Sun 4/117:00 am -
2 stops10h 15m
Deal found 10/25![Southwest logo]()
$527
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/278:40 am -
2 stops8h 57m
Wed 2/36:00 am -
2 stops11h 36m
Deal found 10/27![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 2/45:37 pm -
2 stops20h 15m
Sun 2/77:23 am -
2 stops12h 25m
Deal found 10/28![Delta logo]()
$497
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/52:26 pm -
1 stop6h 23m
Wed 12/97:10 am -
1 stop7h 31m
Deal found 10/26![United Airlines logo]()
$431
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 11/111:35 pm -
1 stop6h 20m
Mon 11/166:50 am -
1 stop6h 50m
Deal found 10/27![Southwest logo]()
$629
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/155:00 am -
1 stop6h 17m
Tue 1/58:50 am -
2 stops11h 44m
Deal found 10/28![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 11/115:45 am -
2 stops13h 30m
Sun 11/155:05 am -
2 stops9h 55m
Deal found 10/27![Southwest logo]()
$639
This United Airlines deal was found by Cheapflights users on 10/28. 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 1/145:00 am -
2 stops9h 22m
Wed 1/206:00 am -
2 stops11h 36m
Deal found 10/28![United Airlines logo]()
$445
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/121:00 pm -
1 stop6h 24m
Mon 11/165:10 am -
2 stops11h 00m
Deal found 10/28![United Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 10/27. 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.
Mon 12/217:00 am -
2 stops14h 10m
Sat 12/2612:25 pm -
2 stops13h 35m
Deal found 10/27![Southwest logo]()
$702
Last-minute flights from Oregon to KentuckyDiscover last-minute flight deals from Oregon to Kentucky. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Kentucky. Data last updated October 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1611:49 pm -
1 stop7h 33m
Fri 11/201:14 pm -
1 stop10h 15m
Deal found 10/25![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1711:51 am -
1 stop6h 51m
Fri 11/206:55 pm -
1 stop7h 51m
Deal found 10/26![Delta logo]()
$331
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 11/1812:35 am -
1 stop8h 25m
Sun 11/226:00 am -
1 stop7h 41m
Deal found 10/29![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/192:24 pm -
1 stop6h 46m
Sat 11/217:00 pm -
1 stop7h 46m
Deal found 10/29![Delta logo]()
$311
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 11/1910:15 am -
2 stops9h 40m
Sat 11/218:30 pm -
1 stop7h 55m
Deal found 10/29![Southwest logo]()
$380
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 11/235:00 am -
1 stop6h 22m
Wed 12/23:20 pm -
1 stop9h 17m
Deal found 10/29![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 11/237:27 pm -
2 stops13h 33m
Tue 12/17:05 am -
2 stops14h 55m
Deal found 10/29![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/2411:51 am -
1 stop8h 22m
Thu 12/36:35 am -
1 stop7h 13m
Deal found 10/28![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 11/247:25 pm -
2 stops11h 13m
Thu 12/33:20 pm -
1 stop9h 17m
Deal found 10/29![United Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop9h 08m
Thu 12/31:10 pm -
1 stop9h 45m
Deal found 10/28![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 11/247:27 pm -
2 stops13h 33m
Wed 12/23:12 pm -
2 stops10h 49m
Deal found 10/29![Delta logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/2511:30 pm -
1 stop7h 14m
Thu 12/37:10 am -
2 stops10h 28m
Deal found 10/28![United Airlines logo]()
$403
One-way flights from Oregon to KentuckySearch for one-way flight options from Oregon to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Oregon to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/811:20 am -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 10/29. 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 2/210:50 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/246:50 am -
1 stop9h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1810:20 am -
2 stops10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/85:10 pm -
3 stops20h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/101:58 pm -
3 stops47h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/1010:15 am -
2 stops9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 1/194:29 pm -
3 stops46h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 12/15:09 pm -
3 stops43h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:45 am -
2 stops10h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$242
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/2411:42 pm -
2 stops14h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$254
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3011:30 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Southwest logo]()
$274
Find flight deals from Oregon to Kentucky
Keep the following information in mind while searching for Oregon to Kentucky flight deals. Data was last updated October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (Southwest) |
One-way from | $156 (Southwest) |
Popular in | December |
Cheapest in | October |
Average price | $412 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon 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 30, 2026.
Use the filters below to find and compare flights from Oregon 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
Thu 12/10
6:30 am-6:55 pm
1 stop9h 25m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$156
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Tue 12/8
10:15 am-10:55 pm
2 stops9h 40m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$161
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Thu 12/24
6:50 am-7:11 pm
1 stop9h 21m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$189
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Mon 1/18
7:45 am-5:50 pm
1 stop7h 05m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$189
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Thu 12/10
1:58 pm-4:32 pm
3 stops47h 34m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$207
EugeneLouisville
EUG Eugene - SDF Louisville Intl
EUGSDF
Eugene
Tue 12/1
6:45 am-8:35 pm
2 stops10h 50m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$242
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Thu 12/24
11:42 pm-5:20 pm
2 stops14h 38m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$254
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Mon 11/30
11:30 pm-10:30 am
1 stop8h 00m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$274
EugeneLouisville
EUG Eugene - SDF Louisville Intl
EUGSDF
Eugene
Tue 12/1
1:06 pm-10:25 pm
1 stop6h 19m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$280
MedfordLouisville
MFR Medford - SDF Louisville Intl
MFRSDF
Medford
Tue 12/1
5:21 pm-9:08 am
2 stops12h 47m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$294
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oregon to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Oregon with our price prediction graph.
PDX-SDF
MFR-SDF
MFR-LEX
RDM-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 Oregon to Kentucky
USOR-USKY
PDX-SDF
MFR-SDF
MFR-LEX
RDM-SDF
What is the cheapest month to book a flight from Oregon to Kentucky?
Currently, January is the cheapest month in which you can book a flight from Oregon to Kentucky (average of $417). Flying from Oregon 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 Oregon to Kentucky?
Airfare is below average for this route at the moment.
Oregon to Kentucky flights typically cost between $414 and $627 in December.The cheapest round-trip price found within the last 5 days was $311 on Southwest (Dec 3-Dec 7).
How far ahead should I book a flight from Oregon to Kentucky?
To ensure you get the cheapest price possible for a flight from Oregon to Kentucky, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 30, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Oregon to Kentucky to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Overall
7.9
Crew
8.6
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Oregon 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 Oregon 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 Oregon to Kentucky by cabin class
Find flights from Oregon to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oregon and Kentucky flights
Browse other Oregon and Kentucky flight options. Last updated on October 30, 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 Oregon after your stay in Kentucky
Oregon to Kentucky flights
Consider these flights traveling from Oregon to Kentucky.
Top 4 airlines flying from Oregon to Kentucky
Discover the top 4 airlines that operate flights from Oregon 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$260 | Average$563 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$328 | Average$513 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$354 | Average$496 | FlexibilityNo cancel fee | On-time63% |