$131+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Oct 13 — Oct 201
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
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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 September 13, 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 September 13, 2026.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/262:50 pm -
1 stop13h 26m
Wed 10/287:20 am -
1 stop7h 27m
Deal found 9/10![Multiple Airlines logo]()
$285
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:50 pm -
1 stop13h 48m
Wed 10/71:21 pm -
1 stop25h 34m
Deal found 9/8![Frontier logo]()
$293
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:50 pm -
1 stop13h 26m
Wed 10/219:00 am -
1 stop7h 23m
Deal found 9/10![Multiple Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/48:59 am -
2 stops10h 31m
Sat 11/76:35 am -
1 stop9h 45m
Deal found 9/7![Delta logo]()
$308
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.
Mon 10/197:37 pm -
1 stop16h 48m
Thu 10/223:49 pm -
1 stop9h 10m
Deal found 9/9![Alaska Airlines logo]()
$309
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:50 pm -
2 stops38h 44m
Thu 10/223:30 pm -
1 stop23h 25m
Deal found 9/11![Frontier logo]()
$313
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:30 am -
2 stops9h 57m
Wed 11/182:03 pm -
2 stops9h 54m
Deal found 9/8![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:35 pm -
2 stops12h 49m
Wed 11/181:31 pm -
2 stops10h 26m
Deal found 9/8![Delta logo]()
$313
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:50 pm -
1 stop13h 26m
Fri 10/306:00 am -
1 stop7h 35m
Deal found 9/12![Multiple Airlines logo]()
$315
This SmartFares 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:22 pm -
1 stop8h 18m
Mon 11/22:15 pm -
1 stop9h 16m
Deal found 9/11![Alaska Airlines logo]()
$316
This Expedia deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/1511:06 am -
1 stop17h 28m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 9/8![Frontier logo]()
$317
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 10/24:20 pm -
1 stop6h 39m
Mon 10/57:16 pm -
1 stop15h 40m
Deal found 9/10![Alaska Airlines logo]()
$320
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 September 13, 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 September 13, 2026.
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 11/48:59 am -
2 stops10h 31m
Sat 11/76:35 am -
1 stop9h 45m
Deal found 9/7![Delta logo]()
$308
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 12/109:53 am -
1 stop9h 02m
Sun 12/138:42 pm -
1 stop15h 00m
Deal found 9/10![Alaska Airlines logo]()
$349
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 11/78:28 am -
Nonstop3h 47m
Sun 11/158:40 am -
Nonstop3h 51m
Deal found 9/12![United Airlines logo]()
$359
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.
Fri 10/211:35 pm -
Nonstop3h 50m
Sat 10/311:00 am -
Nonstop4h 25m
Deal found 9/9![Southwest logo]()
$372
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:36 pm -
1 stop12h 20m
Mon 11/308:05 pm -
1 stop17h 28m
Deal found 9/12![Sun Country Air logo]()
$405
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 11/41:40 pm -
1 stop7h 53m
Sat 11/76:04 am -
1 stop8h 30m
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.
Fri 11/2012:31 pm -
Nonstop3h 34m
Wed 11/258:40 am -
Nonstop3h 51m
Deal found 9/11![United Airlines logo]()
$367
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.
Tue 10/207:09 am -
1 stop7h 41m
Tue 10/272:14 pm -
Nonstop4h 37m
Deal found 9/9![Alaska Airlines logo]()
$367
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 11/41:35 pm -
1 stop5h 50m
Sat 11/76:05 am -
1 stop8h 40m
Deal found 9/8![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/2910:34 am -
2 stops9h 59m
Tue 10/67:35 am -
1 stop5h 41m
Deal found 9/8![Delta logo]()
$354
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 11/412:31 pm -
Nonstop3h 34m
Thu 11/128:40 am -
1 stop6h 05m
Deal found 9/12![United Airlines logo]()
$369
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.
Thu 11/191:35 pm -
1 stop5h 50m
Sun 11/2210:10 am -
1 stop8h 50m
Deal found 9/10![Southwest 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 10/197:20 am -
1 stop29h 05m
Sun 10/256:00 am -
1 stop7h 35m
Deal found 9/10![Alaska Airlines logo]()
$396
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 10/226:45 am -
1 stop9h 08m
Fri 10/236:20 am -
2 stops11h 54m
Deal found 9/9![Delta logo]()
$365
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.
Tue 11/1711:15 am -
1 stop8h 40m
Sat 11/214:50 pm -
1 stop8h 05m
Deal found 9/9![Southwest logo]()
$379
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.
Tue 10/612:52 pm -
1 stop6h 26m
Tue 10/139:05 am -
Nonstop4h 45m
Deal found 9/12![United Airlines logo]()
$389
This Alaska 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:04 am -
2 stops9h 55m
Sat 11/77:20 am -
1 stop8h 17m
Deal found 9/11![Alaska Airlines logo]()
$399
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 10/1612:08 pm -
2 stops8h 57m
Mon 10/195:30 pm -
1 stop7h 29m
Deal found 9/9![Delta logo]()
$365
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/159:15 pm -
1 stop6h 30m
Tue 10/2010:15 am -
2 stops9h 10m
Deal found 9/8![Southwest logo]()
$382
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.
Wed 2/247:02 am -
Nonstop4h 07m
Sun 2/287:55 pm -
1 stop15h 43m
Deal found 9/9![Alaska Airlines logo]()
$408
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.
Thu 11/123:40 pm -
1 stop7h 19m
Sun 11/157:45 pm -
Nonstop4h 42m
Deal found 9/11![United Airlines logo]()
$408
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 10/212:20 pm -
1 stop7h 37m
Wed 10/286:20 am -
1 stop6h 14m
Deal found 9/9![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/2312:50 pm -
1 stop6h 25m
Mon 10/269:45 pm -
Nonstop4h 30m
Deal found 9/8![Southwest logo]()
$382
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.
Thu 10/152:15 pm -
Nonstop4h 11m
Sun 10/189:05 am -
Nonstop4h 45m
Deal found 9/12![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/36:00 am -
1 stop8h 47m
Sat 11/76:04 am -
1 stop9h 34m
Deal found 9/8![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/312:55 pm -
2 stops9h 15m
Mon 10/55:25 am -
1 stop10h 30m
Deal found 9/8![Southwest 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.
Sat 1/168:25 am -
1 stop13h 34m
Wed 1/206:57 pm -
1 stop16h 51m
Deal found 9/10![Alaska Airlines logo]()
$423
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.
Wed 10/211:36 pm -
1 stop6h 29m
Sun 10/256:35 am -
1 stop8h 21m
Deal found 9/10![Delta logo]()
$379
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.
Wed 10/215:50 am -
2 stops8h 15m
Sun 10/256:00 am -
1 stop6h 15m
Deal found 9/9![Southwest 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.
Fri 10/301:35 pm -
1 stop23h 18m
Tue 11/36:35 pm -
1 stop16h 52m
Deal found 9/10![Alaska Airlines logo]()
$423
Last-minute flights from Oregon to ChicagoDiscover last-minute flight deals from Oregon to Chicago. Data last updated September 13, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Chicago. Data last updated September 13, 2026 and is based on user searches.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/112:38 pm -
1 stop9h 45m
Wed 10/71:21 pm -
1 stop24h 05m
Deal found 9/9![Frontier logo]()
$327
This Priceline deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/112:38 pm -
1 stop9h 45m
Thu 10/86:30 am -
1 stop6h 24m
Deal found 9/8![Frontier logo]()
$339
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:20 pm -
1 stop15h 18m
Sun 10/48:55 pm -
1 stop16h 45m
Deal found 9/9![Multiple Airlines logo]()
$341
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.
Sat 10/312:24 pm -
1 stop15h 14m
Wed 10/148:01 pm -
1 stop16h 10m
Deal found 9/10![Frontier logo]()
$329
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:00 am -
Nonstop4h 18m
Sat 10/178:01 pm -
1 stop16h 10m
Deal found 9/9![Multiple Airlines logo]()
$333
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 10/69:03 am -
1 stop7h 50m
Sat 10/108:01 pm -
1 stop16h 10m
Deal found 9/10![Multiple Airlines logo]()
$338
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:11 pm -
1 stop15h 05m
Sat 10/178:01 pm -
1 stop16h 10m
Deal found 9/9![Frontier logo]()
$335
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:11 pm -
1 stop15h 05m
Tue 10/136:30 am -
1 stop6h 24m
Deal found 9/10![Frontier logo]()
$337
This Expedia deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/1511:06 am -
1 stop17h 28m
Sun 10/186:30 am -
1 stop6h 24m
Deal found 9/8![Frontier logo]()
$317
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1911:06 am -
1 stop17h 28m
Wed 10/218:01 pm -
1 stop16h 10m
Deal found 9/11![Frontier logo]()
$332
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:06 am -
1 stop17h 28m
Tue 10/272:14 pm -
Nonstop4h 37m
Deal found 9/9![Multiple Airlines logo]()
$328
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2311:06 am -
1 stop17h 28m
Mon 10/266:30 am -
1 stop30h 37m
Deal found 9/9![Frontier logo]()
$336
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 September 13, 2026.
Search for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated September 13, 2026.
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:50 pm -
1 stop13h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$131
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/82:49 pm -
1 stop13h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$136
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/52:50 pm -
1 stop13h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Frontier logo]()
$139
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.
Mon 10/122:50 pm -
2 stops38h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$141
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:50 pm -
1 stop13h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/12![Frontier logo]()
$146
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:50 pm -
2 stops38h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$149
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/122:49 pm -
1 stop13h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$152
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 10/216:43 am -
1 stop9h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Alaska Airlines logo]()
$155
This CheapOair deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:56 pm -
1 stop15h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$157
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.
Sat 10/176:04 pm -
1 stop10h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Alaska Airlines logo]()
$160
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.
Sun 10/182:39 pm -
2 stops37h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Multiple Airlines logo]()
$162
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:24 pm -
Nonstop3h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$165
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 September 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $285 (Expedia) |
One-way from | $131 (Expedia) |
Popular in | November |
Cheapest in | January |
Average price | $374 |
Good round-trip deal | $359 or less |
Good one-way deal | $203 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 September 13, 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
BoiseChicago
BOI Boise Air Term. Gowen Fld - ORD Chicago O'Hare Intl
BOIORD
Boise Air Term. Gowen Fld
Wed 10/21
6:43 am-4:50 pm
1 stop9h 07m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
BoiseChicago
BOI Boise Air Term. Gowen Fld - ORD Chicago O'Hare Intl
BOIORD
Boise Air Term. Gowen Fld
Sat 10/17
6:04 pm-5:40 am
1 stop10h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$160
MedfordChicago
MFR Medford - ORD Chicago O'Hare Intl
MFRORD
Medford
Sun 10/18
2:39 pm-6:34 am
2 stops37h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$162
BoiseChicago
BOI Boise Air Term. Gowen Fld - ORD Chicago O'Hare Intl
BOIORD
Boise Air Term. Gowen Fld
Fri 11/13
8:20 am-5:37 pm
1 stop8h 17m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$170
BoiseChicago
BOI Boise Air Term. Gowen Fld - ORD Chicago O'Hare Intl
BOIORD
Boise Air Term. Gowen Fld
Tue 11/10
8:59 pm-5:40 am
1 stop7h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$170
BoiseChicago
BOI Boise Air Term. Gowen Fld - MDW Chicago Midway
BOIMDW
Boise Air Term. Gowen Fld
Sat 11/7
5:30 am-11:47 am
1 stop5h 17m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
BoiseChicago
BOI Boise Air Term. Gowen Fld - MDW Chicago Midway
BOIMDW
Boise Air Term. Gowen Fld
Mon 11/9
8:30 pm-5:40 am
1 stop8h 10m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
BoiseChicago
BOI Boise Air Term. Gowen Fld - MDW Chicago Midway
BOIMDW
Boise Air Term. Gowen Fld
Mon 10/5
11:10 pm-10:03 am
1 stop9h 53m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
BoiseChicago
BOI Boise Air Term. Gowen Fld - MDW Chicago Midway
BOIMDW
Boise Air Term. Gowen Fld
Mon 12/7
1:47 pm-10:55 pm
1 stop8h 08m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
BoiseChicago
BOI Boise Air Term. Gowen Fld - MDW Chicago Midway
BOIMDW
Boise Air Term. Gowen Fld
Tue 12/8
1:47 pm-10:55 pm
1 stop8h 08m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$175
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.
BOI-ORD
MFR-ORD
PDX-ORD
RDM-ORD
PDX-MDW
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
BOI-ORD
MFR-ORD
PDX-ORD
RDM-ORD
What is the cheapest month to book a flight from Oregon to Chicago?
Currently, January is the cheapest month in which you can book a flight from Oregon to Chicago (average of $292). Flying from Oregon to Chicago in December is currently the most expensive (average of $430). 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 September 13, 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 35% versus a flight at noon.
Weekly flight availability from Oregon to Chicago
Explore weekly flight availability from Oregon to Chicago. 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 13, 2026.
The most flights from USOR to CHI 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 (21 on average).
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 $347 and $458 in November.The cheapest round-trip price found within the last 5 days was $313 on Delta (Nov 10-Nov 18).
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 September 12, 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. Sunday 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
Chicago flight routes
Complete your trip
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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 September 13, 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 September 13, 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 September 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$243 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$445 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$237 | Average$466 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$365 | FlexibilityNo cancel fee | On-time63% |