$182+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — SDF
Nov 18 — Nov 251
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 October 19, 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 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/101:15 pm -
1 stop6h 09m
Sat 11/145:10 am -
1 stop9h 42m
Deal found 10/14![United Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/811:09 pm -
1 stop7h 29m
Fri 11/131:14 pm -
1 stop9h 33m
Deal found 10/14![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/3111:59 am -
1 stop8h 24m
Sat 1/96:00 am -
1 stop7h 56m
Deal found 10/16![Delta logo]()
$397
This American Airlines deal was found by Cheapflights users on 10/17. 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 12/110:00 pm -
1 stop9h 17m
Tue 12/83:54 pm -
1 stop10h 55m
Deal found 10/17![American Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/811:30 pm -
1 stop7h 35m
Fri 11/131:05 pm -
2 stops13h 25m
Deal found 10/14![Southwest logo]()
$400
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Tue 12/17:25 pm -
2 stops11h 39m
Tue 12/810:50 am -
1 stop7h 29m
Deal found 10/17![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 10/16![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/3011:30 pm -
1 stop8h 00m
Wed 1/68:30 am -
2 stops10h 55m
Deal found 10/16![Southwest logo]()
$412
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/2111:30 pm -
1 stop7h 35m
Tue 11/247:15 pm -
2 stops9h 00m
Deal found 10/15![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/66:20 am -
1 stop8h 10m
Wed 12/97:35 pm -
1 stop6h 50m
Deal found 10/16![Southwest logo]()
$427
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Sun 11/1511:30 pm -
1 stop7h 43m
Sun 11/229:00 am -
1 stop7h 22m
Deal found 10/17![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 10/17. 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.
Fri 11/611:00 pm -
1 stop8h 09m
Mon 11/93:38 pm -
1 stop9h 19m
Deal found 10/17![Delta logo]()
$479
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 19, 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 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/108:30 am -
1 stop8h 00m
Sat 11/145:57 pm -
1 stop7h 30m
Deal found 10/14![United Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:25 am -
2 stops8h 30m
Sat 11/148:40 am -
2 stops11h 05m
Deal found 10/14![Southwest logo]()
$407
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 1/159:45 pm -
1 stop9h 09m
Fri 1/226:36 am -
1 stop8h 48m
Deal found 10/16![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/92:26 pm -
1 stop6h 30m
Sat 12/128:45 am -
1 stop9h 34m
Deal found 10/14![United Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Fri 2/1210:56 pm -
2 stops11h 17m
Tue 2/162:00 pm -
1 stop8h 17m
Deal found 10/17![United Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 10/17. 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.
Fri 11/611:00 pm -
1 stop8h 09m
Mon 11/93:38 pm -
1 stop9h 19m
Deal found 10/17![Delta logo]()
$479
This Southwest deal was found by Cheapflights users on 10/18. 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.
Thu 12/2411:20 am -
1 stop6h 15m
Thu 12/316:50 am -
1 stop6h 50m
Deal found 10/18![Southwest logo]()
$487
This Delta deal was found by Cheapflights users on 10/18. 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 11/2011:20 pm -
1 stop7h 49m
Sun 11/226:00 am -
1 stop7h 41m
Deal found 10/18![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 10/18. 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.
Sun 11/111:30 pm -
1 stop7h 35m
Tue 11/104:15 pm -
1 stop8h 35m
Deal found 10/18![Southwest logo]()
$488
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/14![United Airlines logo]()
$483
This Southwest deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/205:10 am -
2 stops9h 20m
Tue 11/242:10 pm -
1 stop13h 00m
Deal found 10/16![Southwest logo]()
$498
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/2411:20 pm -
1 stop7h 49m
Sat 11/286:00 am -
1 stop7h 41m
Deal found 10/14![Delta logo]()
$501
This United Airlines deal was found by Cheapflights users on 10/18. 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 11/2011:30 pm -
1 stop7h 08m
Sun 11/223:24 pm -
2 stops10h 22m
Deal found 10/18![United Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 10/18. 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.
Sat 12/1211:10 pm -
1 stop9h 37m
Wed 12/165:59 pm -
1 stop7h 08m
Deal found 10/18![Delta logo]()
$518
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/3010:46 am -
1 stop6h 51m
Tue 2/26:00 am -
1 stop8h 31m
Deal found 10/14![United Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3011:42 pm -
2 stops10h 36m
Tue 1/57:00 am -
1 stop8h 14m
Deal found 10/16![United Airlines logo]()
$532
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Sat 12/128:50 am -
2 stops12h 06m
Wed 12/165:00 am -
1 stop9h 41m
Deal found 10/17![United Airlines logo]()
$534
Last-minute flights from Portland to KentuckyDiscover last-minute flight deals from Portland to Kentucky. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Kentucky. Data last updated October 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/17. 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.
Thu 10/296:30 am -
1 stop9h 41m
Tue 11/35:14 am -
1 stop10h 14m
Deal found 10/17![American Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Thu 10/292:34 pm -
1 stop6h 20m
Tue 11/37:10 am -
2 stops9h 12m
Deal found 10/17![United Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 10/17. 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.
Fri 11/611:00 pm -
1 stop8h 09m
Mon 11/93:38 pm -
1 stop9h 19m
Deal found 10/17![Delta logo]()
$479
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/811:09 pm -
1 stop7h 29m
Fri 11/131:14 pm -
1 stop9h 33m
Deal found 10/14![American Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/811:30 pm -
1 stop7h 35m
Fri 11/131:05 pm -
2 stops13h 25m
Deal found 10/14![Southwest logo]()
$400
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/101:15 pm -
1 stop6h 09m
Sat 11/145:10 am -
1 stop9h 42m
Deal found 10/14![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 10/16![Delta logo]()
$407
This Southwest deal was found by Cheapflights users on 10/18. 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.
Tue 11/106:30 am -
1 stop9h 25m
Sat 11/149:10 am -
1 stop6h 50m
Deal found 10/18![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Sun 11/1511:30 pm -
1 stop7h 43m
Sun 11/229:00 am -
1 stop7h 22m
Deal found 10/17![United Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/2011:11 pm -
1 stop7h 17m
Tue 11/245:22 pm -
1 stop9h 54m
Deal found 10/16![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 10/18. 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 11/2011:20 pm -
1 stop7h 49m
Sun 11/226:00 am -
1 stop7h 41m
Deal found 10/18![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/2111:30 pm -
1 stop7h 35m
Tue 11/247:15 pm -
2 stops9h 00m
Deal found 10/15![Southwest logo]()
$418
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 19, 2026.
Search for one-way flight options from Portland to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/14![American Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/75:30 am -
2 stops10h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/2211:11 pm -
1 stop7h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![American Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/14![United Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1012:02 pm -
3 stops24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1212:02 pm -
2 stops48h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 11/225:00 am -
2 stops10h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/14![Southwest logo]()
$237
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 4/156:00 am -
1 stop7h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![American Airlines logo]()
$244
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/49:00 am -
2 stops10h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/72:06 pm -
1 stop18h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![American Airlines logo]()
$358
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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $363 (United Airlines) |
One-way from | $182 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $412 |
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 19, 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
Sat 11/7
5:00 am-2:22 pm
1 stop6h 22m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$182
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Mon 11/9
9:00 pm-10:30 am
2 stops10h 30m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$187
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Tue 11/10
5:00 am-4:57 pm
2 stops8h 57m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$187
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Sun 11/22
11:11 pm-9:28 am
1 stop7h 17m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$194
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Sun 11/8
11:10 pm-1:03 pm
1 stop10h 53m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$214
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Fri 11/6
9:00 pm-10:15 am
2 stops10h 15m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$237
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Fri 11/13
7:26 pm-1:37 pm
2 stops15h 11m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$247
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Thu 4/15
8:15 pm-10:15 am
2 stops11h 00m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$249
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
$274
PortlandLouisville
PDX Portland - SDF Louisville Intl
PDXSDF
Portland
Tue 12/22
11:30 pm-10:00 am
1 stop7h 30m
Louisville Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$274
Showing 1-10 of 37 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 $431). 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 $514 in November.The cheapest round-trip price found within the last 5 days was $363 on United Airlines (Nov 10-Nov 14).
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 19, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
7.9
Crew
8.6
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 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 October 19, 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$292 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$339 | Average$496 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$341 | Average$511 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$354 | Average$496 | FlexibilityNo cancel fee | On-time63% |