$129+ Cheap flights from Oregon to Chicago (CHI)
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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Nov 30 — Dec 71
Round-trip
1 adult, Economy
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Find cheap flights from Oregon to Chicago 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 Oregon to Chicago
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Cheapest flights from Oregon to ChicagoExplore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2026.
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 31, 2026.
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 12/312:39 pm -
1 stop9h 20m
Mon 12/72:13 pm -
1 stop10h 12m
Deal found 10/27![Alaska Airlines logo]()
$271
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.
Fri 12/412:39 pm -
1 stop9h 20m
Thu 12/102:13 pm -
1 stop10h 12m
Deal found 10/27![Alaska Airlines logo]()
$299
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.
Tue 12/110:13 am -
1 stop25h 02m
Mon 12/72:13 pm -
1 stop10h 12m
Deal found 10/27![Alaska Airlines logo]()
$304
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.
Fri 12/411:30 am -
1 stop10h 08m
Wed 12/95:00 am -
1 stop8h 00m
Deal found 10/27![American Airlines logo]()
$314
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.
Fri 12/412:39 pm -
1 stop9h 20m
Fri 12/112:13 pm -
1 stop10h 12m
Deal found 10/27![Alaska Airlines logo]()
$327
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.
Sat 12/56:59 pm -
1 stop8h 38m
Wed 12/99:00 am -
1 stop8h 00m
Deal found 10/27![Alaska Airlines logo]()
$328
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.
Fri 12/412:39 pm -
1 stop9h 20m
Tue 12/82:13 pm -
1 stop23h 44m
Deal found 10/27![Alaska Airlines logo]()
$332
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 12/312:39 pm -
1 stop9h 20m
Sun 12/67:27 am -
1 stop30h 30m
Deal found 10/27![Alaska Airlines logo]()
$334
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.
Tue 12/110:13 am -
1 stop25h 02m
Sat 12/127:27 am -
1 stop14h 22m
Deal found 10/27![Alaska Airlines logo]()
$337
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.
Sun 12/67:02 am -
1 stop9h 58m
Mon 12/72:13 pm -
1 stop10h 12m
Deal found 10/27![Alaska Airlines logo]()
$345
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.
Fri 12/412:39 pm -
1 stop9h 20m
Wed 12/92:13 pm -
1 stop23h 44m
Deal found 10/27![Alaska Airlines logo]()
$350
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 12/115:32 pm -
1 stop10h 05m
Sun 1/37:58 pm -
1 stop15h 31m
Deal found 10/28![Alaska Airlines logo]()
$354
Best flights from Oregon to ChicagoDiscover carefully curated flight deals from Oregon to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
Discover carefully curated flight deals from Oregon to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 31, 2026.
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/123:10 pm -
1 stop12h 45m
Mon 12/141:20 pm -
2 stops10h 30m
Deal found 10/30![Southwest logo]()
$355
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/256:40 am -
2 stops13h 13m
Sun 2/286:30 am -
1 stop7h 38m
Deal found 10/28![Delta 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.
Thu 12/177:00 am -
Nonstop4h 10m
Sun 12/202:17 pm -
1 stop8h 33m
Deal found 10/28![Alaska Airlines logo]()
$364
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.
Thu 11/1911:30 pm -
Nonstop3h 49m
Sat 11/215:48 pm -
1 stop7h 21m
Deal found 10/27![United Airlines logo]()
$368
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 12/25:25 pm -
2 stops10h 30m
Sun 12/68:55 am -
1 stop6h 55m
Deal found 10/28![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2511:50 pm -
Nonstop4h 09m
Thu 12/317:58 pm -
Nonstop4h 49m
Deal found 10/28![United Airlines logo]()
$369
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.
Sat 12/199:22 pm -
1 stop13h 57m
Sun 1/37:58 pm -
1 stop15h 31m
Deal found 10/25![Alaska Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:17 pm -
1 stop6h 42m
Mon 12/73:47 pm -
2 stops9h 52m
Deal found 10/30![Delta logo]()
$372
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.
Fri 12/46:45 am -
1 stop8h 25m
Wed 12/95:05 pm -
1 stop7h 20m
Deal found 10/27![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:17 pm -
1 stop8h 20m
Mon 12/1412:39 pm -
2 stops8h 19m
Deal found 10/30![Delta logo]()
$382
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.
Sun 12/279:45 pm -
1 stop5h 55m
Mon 1/47:58 pm -
1 stop15h 47m
Deal found 10/25![Alaska Airlines logo]()
$387
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 3/66:30 am -
Nonstop3h 59m
Thu 3/119:06 am -
Nonstop4h 51m
Deal found 10/29![United Airlines logo]()
$408
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.
Sat 12/265:50 am -
Nonstop3h 45m
Fri 1/810:00 am -
2 stops10h 05m
Deal found 10/26![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1412:47 pm -
1 stop7h 30m
Mon 1/259:38 am -
2 stops9h 28m
Deal found 10/26![Delta logo]()
$390
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 2/312:33 pm -
1 stop22h 42m
Sat 2/205:55 pm -
1 stop8h 04m
Deal found 10/29![Alaska Airlines logo]()
$391
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.
Thu 1/285:19 am -
2 stops14h 49m
Mon 2/12:13 pm -
1 stop23h 43m
Deal found 10/29![Alaska Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/169:23 am -
2 stops10h 33m
Sun 12/203:29 pm -
1 stop7h 10m
Deal found 10/29![Delta logo]()
$410
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.
Tue 11/102:27 pm -
Nonstop4h 15m
Sat 11/148:40 am -
1 stop6h 45m
Deal found 10/26![United Airlines logo]()
$475
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.
Wed 12/27:12 am -
2 stops14h 47m
Wed 12/96:00 am -
1 stop11h 00m
Deal found 10/26![Alaska Airlines logo]()
$409
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 12/26:09 am -
2 stops13h 26m
Tue 12/812:34 pm -
2 stops13h 25m
Deal found 10/27![Delta logo]()
$415
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.
Tue 11/101:35 pm -
1 stop5h 55m
Sat 11/1410:20 am -
1 stop13h 10m
Deal found 10/26![Southwest logo]()
$494
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.
Sat 11/148:00 am -
1 stop7h 37m
Tue 11/177:20 am -
1 stop14h 15m
Deal found 10/26![Alaska Airlines logo]()
$413
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.
Sun 12/66:09 am -
2 stops9h 52m
Sat 12/1212:39 pm -
2 stops12h 23m
Deal found 10/27![Delta logo]()
$423
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 11/136:15 am -
2 stops9h 25m
Tue 11/171:20 pm -
2 stops11h 05m
Deal found 10/29![Southwest logo]()
$499
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.
Fri 12/46:09 am -
2 stops8h 41m
Sat 12/1210:24 am -
2 stops14h 01m
Deal found 10/27![Delta logo]()
$423
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 1/2312:36 pm -
1 stop7h 32m
Wed 1/276:57 pm -
1 stop7h 02m
Deal found 10/28![Alaska Airlines logo]()
$453
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.
Fri 1/81:30 pm -
1 stop7h 45m
Tue 1/124:00 pm -
2 stops22h 29m
Deal found 10/26![United Airlines logo]()
$612
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/21:33 pm -
1 stop6h 35m
Sat 2/206:00 am -
2 stops9h 04m
Deal found 10/29![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:30 pm -
Nonstop3h 45m
Sun 11/1510:10 am -
Nonstop4h 35m
Deal found 10/25![Southwest logo]()
$522
This United Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/161:40 pm -
1 stop8h 04m
Wed 1/68:03 pm -
2 stops18h 26m
Deal found 10/28![United Airlines logo]()
$612
Last-minute flights from Oregon to ChicagoDiscover last-minute flight deals from Oregon to Chicago. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Chicago. Data last updated October 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:31 pm -
1 stop14h 42m
Tue 11/106:30 am -
1 stop6h 37m
Deal found 10/26![Frontier logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:02 pm -
1 stop10h 19m
Thu 11/196:30 am -
1 stop6h 37m
Deal found 10/30![Frontier logo]()
$359
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:31 pm -
1 stop14h 42m
Thu 11/192:07 pm -
Nonstop4h 43m
Deal found 10/27![Multiple Airlines logo]()
$357
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.
Mon 11/1612:31 pm -
1 stop14h 42m
Sat 11/2110:00 pm -
1 stop14h 28m
Deal found 10/28![Frontier logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:02 pm -
2 stops25h 29m
Thu 11/196:30 am -
1 stop6h 37m
Deal found 10/25![Frontier logo]()
$362
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:10 am -
2 stops7h 30m
Sat 11/2110:00 pm -
Nonstop4h 40m
Deal found 10/27![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:20 am -
Nonstop3h 45m
Wed 11/259:25 pm -
Nonstop4h 45m
Deal found 10/29![Southwest logo]()
$357
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:02 pm -
1 stop10h 19m
Sat 11/216:40 am -
2 stops29h 48m
Deal found 10/27![Frontier logo]()
$358
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 11/207:35 pm -
2 stops11h 29m
Mon 11/232:32 pm -
1 stop8h 24m
Deal found 10/28![Delta logo]()
$356
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/201:58 pm -
1 stop13h 12m
Mon 11/309:01 pm -
1 stop14h 49m
Deal found 10/27![Multiple Airlines logo]()
$364
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 11/212:37 pm -
Nonstop4h 08m
Mon 11/237:45 pm -
Nonstop4h 42m
Deal found 10/27![United Airlines logo]()
$361
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:10 pm -
2 stops24h 43m
Wed 12/27:00 am -
2 stops30h 53m
Deal found 10/28![Frontier logo]()
$355
One-way flights from Oregon to ChicagoSearch for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated October 31, 2026.
Search for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated October 31, 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 1/55:19 am -
1 stop5h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Alaska Airlines logo]()
$129
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 12/911:30 am -
1 stop8h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$135
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.
Mon 12/1412:39 pm -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$136
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.
Mon 11/235:17 am -
1 stop7h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3011:29 am -
2 stops43h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$163
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 12/187:17 am -
1 stop9h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$164
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/277:00 am -
Nonstop4h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Alaska Airlines logo]()
$166
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.
Tue 12/2911:31 pm -
Nonstop3h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
Nonstop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Southwest logo]()
$169
This Priceline deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/29:00 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Alaska Airlines logo]()
$172
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.
Mon 12/145:29 pm -
2 stops29h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$172
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.
Mon 12/711:15 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$173
Find flight deals from Oregon to Chicago
Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $271 (Alaska Airlines) |
One-way from | $129 (Alaska Airlines) |
Popular in | November |
Cheapest in | January |
Average price | $429 |
Good round-trip deal | $384 or less |
Good one-way deal | $228 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Chicago 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 31, 2026.
Use the filters below to find and compare flights from Oregon to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Wed 12/2
6:00 am-11:50 am
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Wed 12/16
10:13 am-1:19 pm
1 stop25h 06m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$174
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Fri 12/25
2:26 pm-8:33 pm
Nonstop4h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - ORD Chicago O'Hare Intl
PDXORD
Portland
Tue 11/17
7:01 am-1:09 pm
Nonstop4h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
Quickest round-trip
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Sat 11/21
11:30 pm-5:15 am
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Thu 1/7
5:19 am-1:13 pm
1 stop5h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Wed 11/18
6:00 am-11:50 am
Nonstop3h 50m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Wed 12/16
11:20 am-5:05 pm
Nonstop3h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Sun 12/6
9:26 pm-5:01 am
1 stop29h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
EugeneChicago
EUG Eugene - ORD Chicago O'Hare Intl
EUGORD
Eugene
Tue 1/19
12:33 pm-10:08 pm
1 stop7h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$182
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oregon to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon with our price prediction graph.
EUG-ORD
EUG-MDW
PDX-ORD
PDX-MDW
MFR-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Oregon to Chicago
USOR-CHI
EUG-ORD
EUG-MDW
PDX-ORD
PDX-MDW
What is the cheapest month to book a flight from Oregon to Chicago?
Currently, February is the cheapest month in which you can book a flight from Oregon to Chicago (average of $298). Flying from Oregon to Chicago in November is currently the most expensive (average of $493). 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 OR to CHI?
Find hourly flight availability from Oregon to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 31, 2026.
When flying from Oregon to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 46% versus a flight at noon.
How much does it cost to fly round-trip from Oregon to Chicago?
Airfare is below average for this route at the moment.
Oregon to Chicago flights typically cost between $362 and $534 in December.The cheapest round-trip price found within the last 5 days was $354 on Alaska Airlines (Dec 11-Jan 3).
How far ahead should I book a flight from Oregon to Chicago?
To ensure you get the cheapest price possible for a flight from Oregon to Chicago, you should look to book at least 71 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 Oregon to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Oregon to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Oregon to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Oregon to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Oregon to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 31, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oregon to Chicago by cabin class
Find flights from Oregon to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oregon and Chicago flights
Browse other Oregon and Chicago flight options. Last updated on October 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oregon to Chicago flights
Consider these flights traveling from Oregon to Chicago.
Top 6 airlines flying from Oregon to Chicago
Discover the top 6 airlines that operate flights from Oregon to Chicago. 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 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$420 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$484 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$216 | Average$357 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$224 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$246 | Average$489 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$375 | FlexibilityNo cancel fee | On-time63% |