$134+ Cheap flights from Chicago (CHI) to Oregon
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 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oregon 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 Chicago to OregonExplore the most affordable flight options available from Chicago to Oregon. 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 Chicago to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:00 am -
1 stop11h 00m
Tue 1/512:33 pm -
1 stop7h 35m
Deal found 10/29![Alaska Airlines logo]()
$257
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 am -
1 stop8h 58m
Sat 11/215:27 pm -
1 stop10h 29m
Deal found 10/28![Alaska Airlines logo]()
$271
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:00 am -
1 stop10h 23m
Tue 12/1511:30 am -
1 stop10h 08m
Deal found 10/29![American Airlines logo]()
$301
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:00 am -
1 stop16h 48m
Tue 12/297:59 pm -
1 stop7h 41m
Deal found 10/28![Alaska Airlines logo]()
$327
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:20 am -
1 stop14h 15m
Sat 11/212:01 pm -
1 stop7h 58m
Deal found 10/29![Alaska Airlines logo]()
$341
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:00 am -
1 stop8h 00m
Wed 12/911:30 am -
1 stop10h 08m
Deal found 10/27![American Airlines logo]()
$345
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 12/26:05 am -
1 stop6h 35m
Wed 12/911:15 am -
1 stop8h 45m
Deal found 10/27![Southwest logo]()
$345
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:27 am -
1 stop30h 30m
Mon 12/217:17 am -
1 stop28h 02m
Deal found 10/29![Alaska Airlines logo]()
$350
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:29 pm -
1 stop8h 17m
Sun 12/65:30 am -
2 stops9h 20m
Deal found 10/27![Delta logo]()
$359
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:00 pm -
1 stop14h 28m
Mon 11/301:31 pm -
2 stops33h 22m
Deal found 10/27![Frontier logo]()
$359
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.
Fri 12/41:20 pm -
2 stops11h 00m
Sun 12/67:35 am -
2 stops8h 00m
Deal found 10/29![Southwest logo]()
$360
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:00 am -
1 stop11h 50m
Fri 1/17:09 am -
1 stop8h 50m
Deal found 10/27![Alaska Airlines logo]()
$360
Best flights from Chicago to OregonDiscover carefully curated flight deals from Chicago to Oregon 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 Chicago to Oregon that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/102:13 pm -
1 stop10h 12m
Tue 12/155:28 am -
1 stop5h 42m
Deal found 10/28![Alaska Airlines logo]()
$271
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 12/21:20 pm -
2 stops11h 05m
Wed 12/95:45 am -
2 stops9h 20m
Deal found 10/27![Southwest logo]()
$355
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 11/192:03 pm -
2 stops9h 54m
Sat 11/2112:35 am -
2 stops11h 24m
Deal found 10/29![Delta logo]()
$374
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 12/216:50 am -
1 stop8h 23m
Mon 12/282:15 pm -
1 stop7h 18m
Deal found 10/29![United Airlines logo]()
$421
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 1/76:15 am -
1 stop6h 30m
Sun 1/106:55 am -
2 stops7h 25m
Deal found 10/29![Southwest logo]()
$359
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am -
1 stop9h 24m
Wed 12/301:52 pm -
1 stop8h 07m
Deal found 10/28![Alaska Airlines logo]()
$367
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 11/273:47 pm -
1 stop6h 17m
Sun 12/67:00 am -
1 stop7h 50m
Deal found 10/28![Delta logo]()
$374
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 12/18:40 pm -
Nonstop4h 45m
Fri 12/46:00 am -
Nonstop3h 50m
Deal found 10/25![Southwest logo]()
$364
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:58 pm -
1 stop25h 14m
Sat 1/29:45 pm -
1 stop5h 55m
Deal found 10/27![Alaska Airlines logo]()
$370
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.
Sun 11/227:17 pm -
1 stop6h 34m
Fri 11/272:15 pm -
1 stop7h 44m
Deal found 10/29![Delta 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.
Thu 12/248:40 pm -
Nonstop4h 45m
Mon 12/288:15 pm -
1 stop6h 45m
Deal found 10/29![Southwest logo]()
$367
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:58 pm -
1 stop25h 14m
Sun 1/39:45 pm -
1 stop5h 55m
Deal found 10/27![Alaska Airlines logo]()
$370
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.
Sat 11/213:47 pm -
2 stops8h 39m
Fri 11/277:00 am -
2 stops11h 17m
Deal found 10/26![Delta logo]()
$387
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:17 pm -
1 stop9h 31m
Sun 12/277:17 am -
1 stop14h 42m
Deal found 10/28![Alaska Airlines logo]()
$372
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.
Wed 11/259:25 pm -
Nonstop4h 45m
Fri 11/275:45 am -
Nonstop3h 45m
Deal found 10/28![Southwest logo]()
$381
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:00 am -
1 stop16h 48m
Tue 12/294:12 pm -
1 stop11h 28m
Deal found 10/25![Alaska Airlines logo]()
$374
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.
Fri 11/206:40 am -
1 stop8h 20m
Mon 11/2312:35 pm -
1 stop9h 24m
Deal found 10/29![Delta logo]()
$419
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 11/2610:05 am -
Nonstop4h 30m
Wed 12/211:20 am -
Nonstop3h 45m
Deal found 10/26![Southwest logo]()
$384
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.
Sat 11/147:35 am -
1 stop7h 19m
Wed 11/181:48 pm -
1 stop9h 11m
Deal found 10/29![United Airlines logo]()
$589
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 11/103:59 pm -
1 stop9h 55m
Sat 11/145:28 am -
1 stop5h 41m
Deal found 10/26![Alaska Airlines logo]()
$385
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 12/139:37 am -
2 stops8h 24m
Mon 12/215:20 am -
2 stops10h 24m
Deal found 10/28![Delta logo]()
$429
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 11/196:05 am -
1 stop6h 35m
Sun 11/222:25 pm -
1 stop7h 30m
Deal found 10/26![Southwest logo]()
$402
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 12/126:07 pm -
2 stops20h 20m
Wed 12/161:40 pm -
1 stop7h 19m
Deal found 10/27![United Airlines logo]()
$612
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:00 am -
1 stop7h 16m
Mon 12/217:05 am -
1 stop9h 49m
Deal found 10/29![Alaska Airlines logo]()
$387
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 1/71:59 pm -
2 stops11h 53m
Sat 1/95:25 am -
2 stops9h 28m
Deal found 10/29![Delta logo]()
$429
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.
Fri 11/209:15 pm -
Nonstop4h 40m
Mon 11/234:00 pm -
1 stop7h 10m
Deal found 10/26![Southwest logo]()
$404
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.
Fri 1/89:38 am -
2 stops9h 18m
Wed 1/135:25 am -
2 stops9h 28m
Deal found 10/29![Delta logo]()
$429
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/62:13 pm -
1 stop23h 43m
Wed 1/135:43 pm -
2 stops17h 32m
Deal found 10/29![Alaska Airlines logo]()
$403
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 12/239:30 pm -
Nonstop4h 45m
Mon 12/2810:15 pm -
1 stop9h 05m
Deal found 10/27![Southwest logo]()
$407
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.
Wed 2/241:30 pm -
1 stop25h 32m
Sun 2/281:43 pm -
1 stop7h 22m
Deal found 10/26![United Airlines logo]()
$701
Last-minute flights from Chicago to OregonDiscover last-minute flight deals from Chicago to Oregon. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oregon. Data last updated October 30, 2026 and is based on user searches.
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 11/106:30 am -
1 stop6h 37m
Fri 12/47:51 pm -
2 stops27h 03m
Deal found 10/29![Frontier logo]()
$365
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.
Sun 11/157:57 pm -
1 stop25h 38m
Wed 11/188:55 am -
1 stop8h 04m
Deal found 10/26![Alaska Airlines logo]()
$367
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:20 am -
1 stop14h 15m
Sat 11/212:01 pm -
1 stop7h 58m
Deal found 10/29![Alaska Airlines logo]()
$341
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 am -
1 stop8h 58m
Sat 11/215:27 pm -
1 stop10h 29m
Deal found 10/28![Alaska Airlines logo]()
$271
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 am -
1 stop11h 30m
Fri 11/275:30 am -
1 stop6h 51m
Deal found 10/25![Alaska Airlines logo]()
$360
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.
Thu 11/198:40 pm -
Nonstop4h 45m
Thu 11/267:00 am -
Nonstop3h 45m
Deal found 10/27![Southwest logo]()
$361
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 am -
1 stop8h 58m
Sun 11/227:03 am -
1 stop14h 46m
Deal found 10/29![Alaska Airlines logo]()
$364
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:42 pm -
Nonstop4h 47m
Sun 11/2211:11 pm -
Nonstop4h 04m
Deal found 10/27![American Airlines logo]()
$364
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 11/203:47 pm -
2 stops9h 49m
Fri 11/277:00 am -
2 stops11h 17m
Deal found 10/28![Delta logo]()
$361
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:00 pm -
1 stop14h 28m
Mon 11/301:31 pm -
2 stops33h 22m
Deal found 10/27![Frontier logo]()
$359
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:29 pm -
1 stop8h 17m
Sun 12/65:30 am -
2 stops9h 20m
Deal found 10/27![Delta logo]()
$359
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 11/257:45 pm -
Nonstop4h 42m
Tue 12/12:26 pm -
Nonstop4h 02m
Deal found 10/27![United Airlines logo]()
$363
One-way flights from Chicago to OregonSearch for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:13 pm -
1 stop23h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Alaska Airlines logo]()
$134
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:00 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$136
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.
Thu 12/32:36 pm -
1 stop28h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$146
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.
Wed 1/69:51 am -
2 stops25h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$146
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.
Wed 12/27:00 am -
3 stops34h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$152
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 1/51:00 pm -
2 stops46h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$153
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/53:19 pm -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$164
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/246:01 am -
2 stops40h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$164
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.
Thu 11/195:15 pm -
1 stop20h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$166
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:20 am -
1 stop8h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Alaska Airlines logo]()
$169
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.
Wed 12/1610:00 am -
2 stops28h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$171
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.
Wed 12/1610:40 am -
2 stops27h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$171
Find flight deals from Chicago to Oregon
Keep the following information in mind while searching for Chicago to Oregon flight deals. Data was last updated October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Mytrip) |
One-way from | $134 (Alaska Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $449 |
Good round-trip deal | $357 or less |
Good one-way deal | $214 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Oregon 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 Chicago to Oregon that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoEugene
ORD Chicago O'Hare Intl - EUG Eugene
ORDEUG
Chicago O'Hare Intl
Sat 12/5
9:00 am-3:00 pm
1 stop8h 00m
Eugene
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$136
ChicagoEugene
MDW Chicago Midway - EUG Eugene
MDWEUG
Chicago Midway
Thu 12/17
5:55 am-10:20 am
1 stop6h 25m
Eugene
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$173
ChicagoEugene
MDW Chicago Midway - EUG Eugene
MDWEUG
Chicago Midway
Thu 12/10
6:05 am-10:40 am
1 stop6h 35m
Eugene
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$173
Quickest round-trip
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 11/17
10:00 am-12:35 pm
Nonstop4h 35m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Fri 11/20
3:47 pm-11:51 pm
2 stops10h 04m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$181
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Sat 11/21
3:47 pm-10:26 pm
2 stops8h 39m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$181
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Tue 12/1
12:34 pm-10:06 pm
2 stops11h 32m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$184
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Sun 12/20
8:17 pm-11:06 pm
Nonstop4h 49m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sun 1/10
10:10 am-12:45 pm
Nonstop4h 35m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Fri 12/18
12:58 pm-6:58 pm
1 stop8h 00m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$189
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Oregon
Have a flexible travel schedule? Discover the best time to fly to Oregon from Chicago with our price prediction graph.
ORD-EUG
MDW-EUG
MDW-PDX
ORD-PDX
ORD-RDM
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 Chicago to Oregon
CHI-USOR
ORD-EUG
MDW-EUG
MDW-PDX
ORD-PDX
What is the cheapest month to book a flight from Chicago to Oregon?
Currently, February is the cheapest month in which you can book a flight from Chicago to Oregon (average of $308). Flying from Chicago to Oregon in October is currently the most expensive (average of $453). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to OR?
Find hourly flight availability from Chicago to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2026.
One of the essential ways to save on airfare from Chicago to Oregon is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 48% on airfare.
How much does it cost to fly round-trip from Chicago to Oregon?
Airfare is below average for this route at the moment.
Chicago to Oregon flights typically cost between $366 and $580 in January.The cheapest round-trip price found within the last 5 days was $359 on Delta (Jan 21-Jan 24).
How far ahead should I book a flight from Chicago to Oregon?
To ensure you get the cheapest price possible for a flight from Chicago to Oregon, you should look to book at least 63 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.
What is the cheapest day to fly from Chicago to Oregon?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Oregon. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Chicago to Oregon flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Oregon
Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated October 30, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andDelta from Chicago to Oregon by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Overall
7.9
Boarding
8.1
Food
7.0
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentFranzi,Mar 2026
SFO - PDX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Oregon. 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 Chicago to Oregon
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Oregon by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Oregon by cabin class
Find flights from Chicago to Oregon, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Oregon flights
Browse other Chicago and Oregon flight options. Last updated on October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Oregon flights
Consider these flights traveling from Chicago to Oregon.
Top 7 airlines flying from Chicago to Oregon
Discover the top 7 airlines that operate flights from Chicago to Oregon. 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$155 | Average$250 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$478 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$480 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$538 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$374 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$463 | FlexibilityNo cancel fee | On-timeN/A |