$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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SDF
Oct 22 — Oct 291
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Kentucky
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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 September 22, 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 September 22, 2026.
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/1011:58 am -
1 stop7h 48m
Sat 11/145:40 pm -
1 stop7h 30m
Deal found 9/22![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/178:30 am -
1 stop7h 41m
Sat 10/249:04 am -
2 stops9h 01m
Deal found 9/19![United Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/611:52 am -
1 stop6h 46m
Tue 11/106:00 am -
1 stop7h 41m
Deal found 9/18![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/2811:30 pm -
1 stop7h 08m
Fri 10/308:00 am -
2 stops9h 37m
Deal found 9/19![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/1810:47 am -
1 stop7h 05m
Sun 11/2210:37 am -
1 stop7h 46m
Deal found 9/17![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/288:45 pm -
2 stops10h 25m
Fri 10/307:15 am -
2 stops10h 05m
Deal found 9/19![Southwest logo]()
$385
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/162:27 pm -
1 stop6h 32m
Fri 10/235:15 am -
1 stop7h 16m
Deal found 9/18![United Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/1611:09 pm -
1 stop7h 29m
Sat 11/216:48 pm -
1 stop8h 28m
Deal found 9/21![American Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/25:14 am -
1 stop10h 14m
Deal found 9/20![American Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/1211:35 pm -
1 stop7h 30m
Wed 10/144:00 pm -
2 stops9h 15m
Deal found 9/18![Southwest logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/258:50 am -
2 stops12h 09m
Mon 1/45:50 pm -
1 stop7h 57m
Deal found 9/22![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/1811:25 am -
2 stops8h 30m
Mon 11/235:35 pm -
2 stops10h 50m
Deal found 9/20![Southwest logo]()
$405
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 September 22, 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 September 22, 2026.
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/106:00 am -
1 stop9h 26m
Sat 11/147:13 pm -
1 stop7h 30m
Deal found 9/17![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/1110:15 am -
2 stops9h 40m
Wed 11/187:20 am -
2 stops8h 50m
Deal found 9/17![Southwest logo]()
$310
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/1810:47 am -
1 stop7h 05m
Sun 11/2210:37 am -
1 stop7h 46m
Deal found 9/17![United Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/1911:12 pm -
1 stop7h 36m
Mon 10/265:53 pm -
1 stop7h 09m
Deal found 9/20![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/1311:30 pm -
1 stop7h 45m
Sat 11/2110:55 am -
2 stops12h 20m
Deal found 9/22![Southwest logo]()
$430
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/911:12 pm -
1 stop7h 36m
Tue 10/131:04 pm -
1 stop9h 05m
Deal found 9/22![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/57:33 pm -
2 stops11h 01m
Wed 10/75:15 am -
2 stops12h 12m
Deal found 9/17![United Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/1810:10 am -
2 stops7h 30m
Sun 11/225:35 pm -
2 stops10h 50m
Deal found 9/18![Southwest logo]()
$437
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/46:59 am -
1 stop9h 11m
Mon 11/96:55 pm -
1 stop7h 51m
Deal found 9/18![Delta logo]()
$461
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/167:29 pm -
2 stops10h 59m
Fri 10/236:05 pm -
1 stop7h 18m
Deal found 9/18![United Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 28m
Wed 12/97:10 am -
1 stop7h 31m
Deal found 9/20![United Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/71:44 pm -
1 stop6h 07m
Tue 10/131:59 pm -
1 stop8h 10m
Deal found 9/22![Delta logo]()
$485
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 1/307:01 am -
1 stop7h 16m
Tue 2/21:50 pm -
1 stop7h 49m
Deal found 9/19![United Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/152:27 pm -
1 stop6h 28m
Sun 10/186:00 am -
1 stop8h 33m
Deal found 9/19![United Airlines logo]()
$588
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/295:00 am -
2 stops8h 38m
Sat 1/25:50 pm -
1 stop7h 57m
Deal found 9/18![United Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/282:34 pm -
1 stop6h 20m
Mon 11/27:10 am -
2 stops16h 05m
Deal found 9/22![United Airlines logo]()
$613
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/72:27 pm -
1 stop6h 28m
Mon 10/126:05 pm -
1 stop7h 18m
Deal found 9/22![United Airlines logo]()
$698
Last-minute flights from Portland to KentuckyDiscover last-minute flight deals from Portland to Kentucky. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Kentucky. Data last updated September 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/511:10 pm -
1 stop7h 49m
Wed 10/77:00 am -
1 stop6h 34m
Deal found 9/17![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/57:33 pm -
2 stops11h 01m
Wed 10/71:25 pm -
1 stop11h 02m
Deal found 9/17![United Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/1211:30 pm -
1 stop7h 04m
Wed 10/145:15 am -
1 stop7h 16m
Deal found 9/18![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/1211:35 pm -
1 stop7h 30m
Wed 10/144:00 pm -
2 stops9h 15m
Deal found 9/18![Southwest logo]()
$400
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/152:27 pm -
1 stop6h 32m
Sun 10/185:15 am -
1 stop7h 16m
Deal found 9/18![United Airlines logo]()
$415
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/162:27 pm -
1 stop6h 32m
Fri 10/235:15 am -
1 stop7h 16m
Deal found 9/18![United Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/178:30 am -
1 stop7h 41m
Sat 10/249:04 am -
2 stops9h 01m
Deal found 9/19![United Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Fri 10/239:44 pm -
1 stop10h 33m
Mon 10/263:36 pm -
1 stop8h 08m
Deal found 9/17![American Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/285:00 am -
1 stop6h 22m
Fri 10/305:10 am -
1 stop9h 42m
Deal found 9/19![United Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/288:45 pm -
2 stops10h 25m
Fri 10/307:15 am -
2 stops10h 05m
Deal found 9/19![Southwest logo]()
$385
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/25:14 am -
1 stop10h 14m
Deal found 9/20![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Fri 10/3010:55 pm -
1 stop7h 37m
Sun 11/15:26 pm -
1 stop9h 17m
Deal found 9/18![American Airlines logo]()
$427
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 September 22, 2026.
Search for one-way flight options from Portland to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This American Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1310:55 pm -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$150
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/138:45 pm -
2 stops10h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$174
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 9/18![American Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/208:45 pm -
2 stops10h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/43:40 pm -
2 stops14h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1710:43 am -
2 stops10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/212:38 pm -
3 stops28h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/199:15 pm -
2 stops9h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$237
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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.
Sun 10/1810:55 pm -
1 stop7h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/1911:06 am -
3 stops44h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American 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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Delta) |
One-way from | $150 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $434 |
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 September 22, 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 10/13
8:45 pm-10:05 am
2 stops10h 20m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$174
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
Tue 10/20
8:30 am-7:11 pm
1 stop7h 41m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
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
$182
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Tue 10/20
8:45 pm-10:05 am
2 stops10h 20m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$187
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Wed 11/4
3:40 pm-9:38 am
2 stops14h 58m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$205
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Mon 10/19
9:15 pm-10:05 am
2 stops9h 50m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$237
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Sun 10/18
7:45 am-1:25 am
2 stops14h 40m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$286
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Tue 11/10
6:00 am-6:26 pm
1 stop9h 26m
Louisville Intl
Sat 11/14
7:13 pm-11:43 pm
1 stop7h 30m
$299
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Wed 11/11
10:15 am-10:55 pm
2 stops9h 40m
Louisville Intl
Wed 11/18
7:20 am-1:10 pm
2 stops8h 50m
$310
Showing 1-10 of 30 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, September is the cheapest month in which you can book a flight from Portland to Kentucky (average of $415). 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 typical for this route at the moment.
Portland to Kentucky flights typically cost between $322 and $530 in November.The cheapest round-trip price found within the last 5 days was $363 on Delta (Nov 10-Nov 14).
How far ahead should I book a flight from Portland to Kentucky?
Booking 73 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 September 22, 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
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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
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 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 September 22, 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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$274 | Average$456 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$280 | Average$503 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$339 | Average$507 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$354 | Average$492 | FlexibilityNo cancel fee | On-time63% |