$107+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Oct 15 — Oct 221
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oregon with Cheapflights
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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 September 15, 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 September 15, 2026.
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/204:05 pm -
1 stop8h 54m
Sat 10/2412:26 pm -
Nonstop3h 39m
Deal found 9/14![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 9/14. 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 10/206:04 am -
1 stop8h 30m
Sat 10/241:40 pm -
1 stop7h 53m
Deal found 9/14![Delta logo]()
$247
This Delta deal was found by Cheapflights users on 9/14. 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 10/206:30 am -
1 stop8h 04m
Sat 10/241:40 pm -
1 stop9h 17m
Deal found 9/14![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 9/14. 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 10/206:55 am -
2 stops15h 40m
Sat 10/2411:25 am -
1 stop6h 15m
Deal found 9/14![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 11/266:00 am -
1 stop8h 11m
Tue 12/15:15 am -
1 stop5h 44m
Deal found 9/14![Delta logo]()
$263
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 11/266:23 am -
1 stop8h 28m
Tue 12/13:44 pm -
1 stop7h 18m
Deal found 9/14![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 12/35:45 pm -
1 stop6h 40m
Tue 12/81:35 pm -
1 stop5h 50m
Deal found 9/14![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 9/14. 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.
Fri 11/66:20 am -
1 stop7h 15m
Mon 11/93:38 pm -
1 stop7h 21m
Deal found 9/14![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/295:40 am -
1 stop6h 40m
Sat 10/319:35 am -
1 stop8h 50m
Deal found 9/14![Southwest logo]()
$297
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 11/69:45 am -
Nonstop3h 52m
Mon 11/92:41 pm -
1 stop8h 18m
Deal found 9/14![American Airlines logo]()
$303
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:57 pm -
1 stop18h 31m
Mon 11/94:16 pm -
1 stop6h 43m
Deal found 9/10![Alaska Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/108:40 am -
Nonstop3h 51m
Wed 11/1112:31 pm -
Nonstop3h 34m
Deal found 9/14![United Airlines logo]()
$317
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 September 15, 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 September 15, 2026.
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/295:40 am -
2 stops8h 40m
Sat 10/316:00 am -
2 stops8h 05m
Deal found 9/14![Southwest logo]()
$313
This Alaska Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:35 pm -
1 stop15h 32m
Mon 11/912:49 pm -
1 stop10h 10m
Deal found 9/9![Alaska Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/89:21 pm -
Nonstop4h 38m
Mon 10/126:09 pm -
1 stop9h 50m
Deal found 9/14![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:05 am -
1 stop7h 56m
Sat 10/101:40 pm -
1 stop7h 53m
Deal found 9/9![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:01 am -
Nonstop4h 56m
Sun 11/82:27 pm -
Nonstop4h 13m
Deal found 9/11![United Airlines logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/103:59 pm -
1 stop8h 50m
Wed 11/111:53 pm -
1 stop9h 06m
Deal found 9/10![Alaska Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/225:15 am -
2 stops9h 20m
Mon 10/2611:35 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/199:55 am -
2 stops7h 54m
Sat 1/236:00 am -
2 stops9h 25m
Deal found 9/10![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:40 am -
Nonstop3h 48m
Sat 10/172:44 pm -
1 stop8h 15m
Deal found 9/12![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/1711:00 am -
Nonstop4h 25m
Mon 10/1911:35 pm -
Nonstop3h 50m
Deal found 9/13![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:03 pm -
2 stops9h 05m
Mon 11/93:00 pm -
1 stop5h 33m
Deal found 9/9![Delta logo]()
$365
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:40 am -
1 stop6h 32m
Wed 10/712:52 pm -
1 stop9h 07m
Deal found 9/10![United Airlines logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:07 pm -
Nonstop4h 43m
Sun 11/82:04 pm -
1 stop7h 45m
Deal found 9/14![Alaska Airlines logo]()
$394
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:25 am -
Nonstop4h 35m
Mon 11/97:35 am -
2 stops8h 00m
Deal found 9/9![Southwest logo]()
$368
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:40 am -
1 stop6h 45m
Wed 11/412:59 pm -
1 stop6h 31m
Deal found 9/9![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:15 pm -
1 stop6h 34m
Sun 11/16:05 am -
1 stop8h 48m
Deal found 9/9![Delta logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:14 pm -
Nonstop4h 37m
Sun 10/188:09 am -
1 stop8h 11m
Deal found 9/10![Alaska Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:15 pm -
Nonstop4h 30m
Sat 10/175:50 am -
2 stops10h 15m
Deal found 9/12![Southwest logo]()
$372
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:01 am -
Nonstop4h 56m
Mon 11/162:27 pm -
Nonstop4h 13m
Deal found 9/12![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:40 pm -
1 stop6h 00m
Mon 10/57:15 pm -
2 stops10h 26m
Deal found 9/9![Delta logo]()
$382
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/89:45 pm -
Nonstop4h 30m
Mon 10/1211:35 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:01 am -
Nonstop4h 56m
Sun 11/222:27 pm -
Nonstop4h 13m
Deal found 9/12![United Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:17 pm -
1 stop18h 45m
Sat 10/312:58 pm -
1 stop15h 42m
Deal found 9/10![Alaska Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:03 pm -
2 stops11h 56m
Sun 11/16:05 am -
1 stop8h 48m
Deal found 9/10![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:30 am -
1 stop6h 15m
Sat 11/712:15 pm -
1 stop8h 35m
Deal found 9/9![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:35 am -
1 stop8h 21m
Tue 10/276:05 am -
2 stops10h 05m
Deal found 9/9![Delta logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/216:57 pm -
1 stop27h 58m
Mon 1/258:25 am -
1 stop13h 34m
Deal found 9/10![Alaska Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/308:40 am -
1 stop6h 45m
Mon 11/22:27 pm -
Nonstop4h 13m
Deal found 9/13![United Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:03 pm -
2 stops11h 56m
Wed 11/41:36 pm -
1 stop6h 29m
Deal found 9/9![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:15 am -
1 stop6h 20m
Wed 10/711:15 am -
2 stops9h 30m
Deal found 9/10![Southwest logo]()
$384
Last-minute flights from Chicago to OregonDiscover last-minute flight deals from Chicago to Oregon. Data last updated September 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oregon. Data last updated September 15, 2026 and is based on user searches.
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:16 pm -
1 stop15h 40m
Sat 10/172:06 pm -
1 stop14h 34m
Deal found 9/10![Alaska Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 9/14. 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 10/169:45 pm -
Nonstop4h 30m
Wed 10/2111:35 pm -
Nonstop3h 50m
Deal found 9/14![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/14. 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.
Sat 10/1711:00 am -
Nonstop4h 25m
Tue 10/278:00 pm -
1 stop7h 50m
Deal found 9/14![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/204:05 pm -
1 stop8h 54m
Sat 10/2412:26 pm -
Nonstop3h 39m
Deal found 9/14![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 9/14. 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 10/205:45 am -
1 stop6h 55m
Sat 10/2411:25 am -
1 stop6h 15m
Deal found 9/14![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 9/14. 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 10/206:04 am -
1 stop8h 30m
Sat 10/246:00 am -
2 stops9h 47m
Deal found 9/14![Delta logo]()
$252
This Delta deal was found by Cheapflights users on 9/14. 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 10/206:20 am -
2 stops10h 00m
Sat 10/241:06 pm -
1 stop7h 59m
Deal found 9/14![Delta logo]()
$252
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/2211:35 am -
Nonstop3h 58m
Sun 10/252:41 pm -
1 stop8h 18m
Deal found 9/14![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/231:46 pm -
1 stop9h 25m
Wed 10/281:12 pm -
Nonstop4h 23m
Deal found 9/14![American Airlines logo]()
$319
This Orbitz deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:30 am -
1 stop6h 37m
Sun 11/112:31 pm -
1 stop14h 42m
Deal found 9/11![Frontier logo]()
$318
This Southwest deal was found by Cheapflights users on 9/14. 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.
Thu 10/295:40 am -
1 stop6h 40m
Sat 10/319:35 am -
1 stop8h 50m
Deal found 9/14![Southwest logo]()
$297
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:49 pm -
1 stop9h 10m
Sat 10/317:20 am -
1 stop10h 33m
Deal found 9/10![Alaska Airlines logo]()
$320
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 September 15, 2026.
Search for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated September 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/71:21 pm -
1 stop25h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$107
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/2711:35 am -
Nonstop3h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$114
This Delta deal was found by Cheapflights users on 9/14. 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 10/205:27 am -
1 stop9h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$124
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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 10/135:50 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 9/14. 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 11/412:50 pm -
2 stops11h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 12/146:20 am -
1 stop7h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:01 pm -
2 stops42h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$141
This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 11/95:55 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$147
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/271:30 pm -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$151
This Alaska Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:00 am -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Alaska Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 9/14. 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 10/276:20 am -
2 stops11h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$156
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:29 pm -
1 stop7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Alaska Airlines logo]()
$157
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 September 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $247 (Southwest) |
One-way from | $107 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $380 |
Good round-trip deal | $339 or less |
Good one-way deal | $218 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 September 15, 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
ChicagoBoise
MDW Chicago Midway - BOI Boise Air Term. Gowen Fld
MDWBOI
Chicago Midway
Tue 10/13
5:50 pm-11:15 pm
1 stop6h 25m
Boise Air Term. Gowen Fld
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$132
ChicagoBoise
ORD Chicago O'Hare Intl - BOI Boise Air Term. Gowen Fld
ORDBOI
Chicago O'Hare Intl
Fri 12/11
2:54 pm-11:13 pm
1 stop9h 19m
Boise Air Term. Gowen Fld
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
ChicagoBoise
ORD Chicago O'Hare Intl - BOI Boise Air Term. Gowen Fld
ORDBOI
Chicago O'Hare Intl
Sat 12/12
9:00 am-6:23 pm
1 stop10h 23m
Boise Air Term. Gowen Fld
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
ChicagoBoise
ORD Chicago O'Hare Intl - BOI Boise Air Term. Gowen Fld
ORDBOI
Chicago O'Hare Intl
Wed 10/14
7:20 am-1:47 pm
1 stop7h 27m
Boise Air Term. Gowen Fld
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
ChicagoBoise
ORD Chicago O'Hare Intl - BOI Boise Air Term. Gowen Fld
ORDBOI
Chicago O'Hare Intl
Thu 12/10
2:13 pm-10:27 pm
1 stop9h 14m
Boise Air Term. Gowen Fld
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$170
ChicagoBoise
ORD Chicago O'Hare Intl - BOI Boise Air Term. Gowen Fld
ORDBOI
Chicago O'Hare Intl
Thu 11/12
5:30 am-1:39 pm
1 stop9h 09m
Boise Air Term. Gowen Fld
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$175
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 10/27
8:40 pm-11:10 pm
Nonstop4h 30m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Mon 11/9
9:15 pm-11:55 pm
Nonstop4h 40m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 10/14
8:40 pm-11:10 pm
Nonstop4h 30m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 10/10
7:15 pm-9:45 pm
Nonstop4h 30m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
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-BOI
MDW-BOI
ORD-PDX
MDW-PDX
ORD-EUG
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-BOI
MDW-BOI
ORD-PDX
MDW-PDX
What is the cheapest month to book a flight from Chicago to Oregon?
Currently, January is the cheapest month in which you can book a flight from Chicago to Oregon (average of $308). Flying from Chicago to Oregon in June is currently the most expensive (average of $424). 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 September 15, 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.
Weekly flight availability from Chicago to Oregon
Explore weekly flight availability from Chicago to Oregon. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2026.
The most flights from CHI to USOR are scheduled on a Friday (31 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Chicago to Oregon?
Airfare is typical for this route at the moment.
Chicago to Oregon flights typically cost between $317 and $470 in October.The cheapest round-trip price found within the last 5 days was $318 on Frontier (Oct 27-Nov 1).
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 86 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 September 12, 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 September 15, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, 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
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
8.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 September 15, 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 September 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$155 | Average$338 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$206 | Average$472 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$213 | Average$461 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$217 | Average$538 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$447 | FlexibilityNo cancel fee | On-timeN/A |