$125+ Cheap flights from Chicago (CHI) to Oregon
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Aug 29 — Sep 51
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 July 30, 2026.
Explore the most affordable flight options available from Chicago to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2026.
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:21 pm
ORD
- BOI
1 stop25h 34m
Frontier
Mon 9/142:50 pm
BOI
- ORD
1 stop13h 48m
Frontier
Deal found 7/27![Frontier logo]()
$260
This CheapTickets deal was found by Cheapflights users on 7/28. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:00 am
ORD
- BOI
1 stop8h 30m
Alaska Airlines
Sat 9/194:20 pm
BOI
- ORD
1 stop6h 39m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$282
This Frontier deal was found by Cheapflights users on 7/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:50 am
ORD
- BOI
1 stop9h 07m
Frontier
Mon 10/263:52 pm
BOI
- ORD
1 stop12h 50m
Frontier
Deal found 7/26![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Thu 8/2012:24 pm
BOI
- ORD
1 stop24h 12m
Frontier
Deal found 7/27![Frontier logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:55 pm
ORD
- BOI
1 stop18h 00m
Frontier
Mon 9/142:50 pm
BOI
- ORD
1 stop13h 48m
Frontier
Deal found 7/29![Frontier logo]()
$288
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/51:02 pm
ORD
- BOI
1 stop26h 55m
Frontier
Mon 11/93:52 pm
BOI
- ORD
1 stop12h 43m
Frontier
Deal found 7/29![Frontier logo]()
$292
This Orbitz deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am
ORD
- BOI
1 stop7h 35m
Alaska Airlines
Mon 10/198:22 pm
BOI
- ORD
1 stop8h 18m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$293
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:57 pm
ORD
- BOI
1 stop15h 32m
Multiple Airlines
Mon 8/247:48 pm
BOI
- ORD
1 stop9h 32m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$296
This SmartFares deal was found by Cheapflights users on 7/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
ORD
- BOI
1 stop9h 22m
Alaska Airlines
Tue 9/152:16 pm
BOI
- ORD
1 stop8h 43m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$297
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:30 am
ORD
- PDX
1 stop7h 13m
Frontier
Thu 10/89:34 pm
PDX
- ORD
1 stop12h 23m
Frontier
Deal found 7/27![Frontier logo]()
$300
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:02 pm
ORD
- PDX
1 stop9h 06m
Frontier
Sun 11/159:03 pm
PDX
- ORD
1 stop12h 54m
Frontier
Deal found 7/27![Frontier logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Tue 9/12:41 pm
ORD
- PDX
1 stop28h 30m
Frontier
Tue 9/85:56 pm
PDX
- ORD
2 stops18h 21m
Frontier
Deal found 7/26![Frontier logo]()
$302
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 July 30, 2026.
Discover carefully curated flight deals from Chicago to Oregon that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 30, 2026.
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:40 am
ORD
- BOI
Nonstop3h 46m
United Airlines
Mon 9/147:05 pm
BOI
- ORD
1 stop8h 56m
United Airlines
Deal found 7/26![United Airlines logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 7/28. 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 9/116:00 am
ORD
- BOI
1 stop7h 35m
Alaska Airlines
Fri 9/185:52 pm
BOI
- ORD
1 stop11h 28m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 9/96:40 am
MDW
- BOI
1 stop5h 15m
Southwest
Wed 9/163:40 pm
BOI
- MDW
1 stop6h 45m
Southwest
Deal found 7/26![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/26. 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.
Tue 10/67:35 am
ORD
- BOI
1 stop5h 41m
Delta
Sat 10/101:40 pm
BOI
- ORD
1 stop9h 12m
Delta
Deal found 7/26![Delta logo]()
$333
This KAYAK deal was found by Cheapflights users on 7/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:00 am
ORD
- PDX
1 stop9h 48m
American Airlines
Wed 8/121:38 pm
PDX
- ORD
1 stop7h 52m
American Airlines
Deal found 7/27![American Airlines logo]()
$539
This Alaska Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am
ORD
- BOI
1 stop9h 22m
Alaska Airlines
Tue 9/227:20 am
BOI
- ORD
1 stop11h 01m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/1912:40 pm
MDW
- BOI
1 stop7h 00m
Southwest
Tue 9/223:40 pm
BOI
- MDW
1 stop6h 45m
Southwest
Deal found 7/29![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/26. 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.
Mon 8/175:56 pm
ORD
- BOI
1 stop6h 57m
Delta
Mon 8/2411:10 pm
BOI
- ORD
2 stops10h 32m
Delta
Deal found 7/26![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:25 am
ORD
- EUG
Nonstop4h 45m
United Airlines
Sat 9/192:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Deal found 7/25![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 7/25. 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 10/222:55 pm
MDW
- BOI
1 stop9h 40m
Southwest
Sat 10/242:25 pm
BOI
- MDW
1 stop5h 30m
Southwest
Deal found 7/25![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/28. 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 10/151:55 pm
ORD
- BOI
2 stops11h 04m
Delta
Mon 10/1911:32 am
BOI
- ORD
1 stop5h 38m
Delta
Deal found 7/28![Delta logo]()
$338
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 10/242:21 pm
ORD
- EUG
1 stop9h 44m
Alaska Airlines
Sat 10/317:00 am
EUG
- ORD
1 stop9h 53m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:50 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Wed 9/210:35 am
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 7/27![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 9/128:05 am
MDW
- BOI
2 stops8h 50m
Southwest
Sat 9/192:25 pm
BOI
- MDW
1 stop5h 25m
Southwest
Deal found 7/29![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:50 pm
ORD
- BOI
1 stop6h 43m
Delta
Sat 10/245:30 am
BOI
- ORD
2 stops9h 56m
Delta
Deal found 7/25![Delta logo]()
$348
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 10/102:21 pm
ORD
- EUG
1 stop9h 44m
Alaska Airlines
Fri 10/167:00 am
EUG
- ORD
1 stop9h 53m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 am
MDW
- BOI
1 stop5h 15m
Southwest
Tue 9/227:05 am
BOI
- MDW
2 stops9h 05m
Southwest
Deal found 7/25![Southwest logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 10/85:00 am
ORD
- PDX
1 stop6h 36m
United Airlines
Mon 10/1211:30 pm
PDX
- ORD
Nonstop4h 01m
United Airlines
Deal found 7/28![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/91:55 pm
ORD
- BOI
2 stops11h 04m
Delta
Tue 9/226:45 am
BOI
- ORD
2 stops10h 19m
Delta
Deal found 7/25![Delta logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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.
Sat 10/247:20 am
ORD
- EUG
1 stop9h 12m
Alaska Airlines
Mon 10/267:23 pm
EUG
- ORD
1 stop8h 17m
Alaska Airlines
Deal found 7/29![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 am
MDW
- BOI
1 stop5h 15m
Southwest
Tue 9/157:05 am
BOI
- MDW
2 stops9h 05m
Southwest
Deal found 7/25![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/81:55 pm
ORD
- BOI
2 stops11h 04m
Delta
Tue 9/156:45 am
BOI
- ORD
2 stops10h 19m
Delta
Deal found 7/25![Delta logo]()
$353
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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 9/97:20 am
ORD
- EUG
1 stop15h 04m
Alaska Airlines
Wed 9/167:08 am
EUG
- ORD
1 stop10h 13m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/27. 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 9/910:30 am
MDW
- BOI
2 stops10h 20m
Southwest
Mon 9/142:55 pm
BOI
- MDW
1 stop6h 05m
Southwest
Deal found 7/27![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:44 pm
ORD
- EUG
1 stop8h 15m
Delta
Tue 9/151:38 pm
EUG
- ORD
1 stop6h 17m
Delta
Deal found 7/25![Delta logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 8/276:01 am
ORD
- BOI
1 stop9h 01m
Alaska Airlines
Sun 8/306:00 am
BOI
- ORD
1 stop6h 26m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 8/276:15 am
MDW
- EUG
1 stop10h 55m
Southwest
Thu 9/31:15 pm
EUG
- MDW
1 stop9h 15m
Southwest
Deal found 7/28![Southwest logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/222:18 pm
ORD
- PDX
1 stop8h 31m
Alaska Airlines
Tue 9/297:06 am
PDX
- ORD
Nonstop4h 20m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 7/26. 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.
Fri 10/95:31 pm
MDW
- BOI
1 stop7h 28m
Delta
Tue 10/135:30 am
BOI
- MDW
1 stop5h 17m
Delta
Deal found 7/26![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Thu 8/62:25 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 7/29![United Airlines logo]()
$483
Last-minute flights from Chicago to OregonDiscover last-minute flight deals from Chicago to Oregon. Data last updated July 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oregon. Data last updated July 30, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 7/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Fri 7/315:49 pm
PDX
- ORD
1 stop9h 48m
Frontier
Deal found 7/26![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 7/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:29 am
ORD
- PDX
1 stop11h 25m
Frontier
Fri 8/215:56 pm
PDX
- ORD
1 stop10h 21m
Frontier
Deal found 7/28![Frontier logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Fri 8/79:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Tue 9/15:56 pm
PDX
- ORD
1 stop17h 40m
Frontier
Deal found 7/28![Frontier logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Fri 8/79:57 pm
ORD
- PDX
1 stop20h 54m
Frontier
Sat 9/55:56 pm
PDX
- ORD
1 stop10h 03m
Frontier
Deal found 7/28![Frontier logo]()
$312
This Frontier deal was found by Cheapflights users on 7/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Sun 8/166:49 pm
PDX
- ORD
1 stop8h 48m
Frontier
Deal found 7/26![Frontier logo]()
$301
This CheapOair deal was found by Cheapflights users on 7/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Tue 8/185:56 pm
PDX
- ORD
1 stop17h 40m
Frontier
Deal found 7/26![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Thu 8/2012:24 pm
BOI
- ORD
1 stop24h 12m
Frontier
Deal found 7/27![Frontier logo]()
$287
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:57 pm
ORD
- BOI
1 stop15h 32m
Multiple Airlines
Mon 8/247:48 pm
BOI
- ORD
1 stop9h 32m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:41 pm
ORD
- PDX
1 stop28h 30m
Frontier
Sun 8/231:47 pm
PDX
- ORD
1 stop27h 15m
Frontier
Deal found 7/27![Frontier logo]()
$307
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:41 pm
ORD
- BOI
1 stop21h 48m
Frontier
Tue 8/251:24 pm
BOI
- ORD
1 stop23h 12m
Frontier
Deal found 7/29![Frontier logo]()
$304
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Tue 8/256:01 am
ORD
- EUG
1 stop8h 40m
Alaska Airlines
Tue 9/12:29 pm
EUG
- ORD
1 stop20h 53m
Alaska Airlines
Deal found 7/28![Alaska Airlines logo]()
$309
This Expedia deal was found by Cheapflights users on 7/27. 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.
Thu 8/272:22 pm
ORD
- PDX
Nonstop4h 28m
Multiple Airlines
Sat 8/295:56 pm
PDX
- ORD
1 stop10h 03m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$304
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 July 30, 2026.
Search for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated July 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Wed 8/262:41 pm
ORD
- BOI
1 stop21h 48m
Frontier
Deal found 7/26![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 7/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:50 am
ORD
- BOI
1 stop9h 07m
Frontier
Deal found 7/25![Frontier logo]()
$126
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:41 pm
ORD
- BOI
1 stop21h 48m
Frontier
Deal found 7/29![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/242:41 pm
ORD
- BOI
1 stop22h 48m
Frontier
Deal found 7/26![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:46 pm
ORD
- BOI
2 stops49h 11m
Frontier
Deal found 7/27![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 7/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:50 am
ORD
- BOI
1 stop9h 07m
Frontier
Deal found 7/25![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:30 am
ORD
- BOI
2 stops32h 25m
Frontier
Deal found 7/29![Frontier logo]()
$144
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 9/266:00 am
ORD
- BOI
1 stop7h 35m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$147
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 10/306:00 am
ORD
- BOI
1 stop8h 50m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Wed 9/231:21 pm
ORD
- BOI
1 stop26h 36m
Frontier
Deal found 7/26![Frontier logo]()
$151
This Southwest deal was found by Cheapflights users on 7/28. 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.
Mon 8/2411:40 am
MDW
- BOI
Nonstop3h 30m
Southwest
Deal found 7/28![Southwest logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 10/1911:06 am
ORD
- PDX
1 stop7h 29m
Frontier
Deal found 7/28![Frontier logo]()
$159
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 July 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $260 (CheapOair) |
One-way from | $125 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $382 |
Good round-trip deal | $325 or less |
Good one-way deal | $200 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 2,558,603 searches. Data last updated July 30, 2026.
Use the filters below to find and compare flights from Chicago to Oregon that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Wed 9/9
8:40 am-11:26 am
Nonstop3h 46m
Boise Air Term. Gowen Fld
Mon 9/14
7:05 pm-5:01 am
1 stop8h 56m
$323
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Fri 9/11
6:00 am-12:35 pm
1 stop7h 35m
Boise Air Term. Gowen Fld
Fri 9/18
5:52 pm-6:20 am
1 stop11h 28m
$324
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Tue 9/8
6:00 am-2:22 pm
1 stop9h 22m
Boise Air Term. Gowen Fld
Tue 9/22
7:20 am-7:21 pm
1 stop11h 01m
$325
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Wed 9/9
6:40 am-10:55 am
1 stop5h 15m
Boise Air Term. Gowen Fld
Wed 9/16
3:40 pm-11:25 pm
1 stop6h 45m
$333
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Tue 10/6
7:35 am-12:16 pm
1 stop5h 41m
Boise Air Term. Gowen Fld
Sat 10/10
1:40 pm-11:52 pm
1 stop9h 12m
$333
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Sat 9/19
12:40 pm-6:40 pm
1 stop7h 00m
Boise Air Term. Gowen Fld
Tue 9/22
3:40 pm-11:25 pm
1 stop6h 45m
$333
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Thu 10/22
2:55 pm-11:35 pm
1 stop9h 40m
Boise Air Term. Gowen Fld
Sat 10/24
2:25 pm-8:55 pm
1 stop5h 30m
$333
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Mon 8/17
5:56 pm-11:53 pm
1 stop6h 57m
Boise Air Term. Gowen Fld
Mon 8/24
11:10 pm-10:42 am
2 stops10h 32m
$338
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Thu 10/15
1:55 pm-11:59 pm
2 stops11h 04m
Boise Air Term. Gowen Fld
Mon 10/19
11:32 am-6:10 pm
1 stop5h 38m
$338
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Sat 9/12
8:05 am-3:55 pm
2 stops8h 50m
Boise Air Term. Gowen Fld
Sat 9/19
2:25 pm-8:50 pm
1 stop5h 25m
$338
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
ORD-EUG
MDW-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
ORD-EUG
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 $305). 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 July 30, 2026.
One of the essential ways to save on airfare from Chicago to Oregon is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 34% 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 July 30, 2026.
The most flights from CHI to USOR are scheduled on a Monday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Chicago to Oregon?
Airfare is below average for this route at the moment.
Chicago to Oregon flights typically cost between $322 and $497 in October.The cheapest round-trip price found within the last 5 days was $300 on Frontier (Oct 2-Oct 8).
How far ahead should I book a flight from Chicago to Oregon?
To ensure you get the cheapest price possible for a flight from Chicago to Oregon, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago to Oregon?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Oregon. Price data was last updated on July 25, 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 July 30, 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.
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Overall
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.
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.
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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 July 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Oregon flights
Consider these flights traveling from Chicago to Oregon.
Top 7 airlines flying from Chicago to Oregon
Discover the top 7 airlines that operate flights from Chicago to Oregon. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$150 | Average$317 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$452 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$207 | Average$547 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$212 | Average$464 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$468 | FlexibilityNo cancel fee | On-timeN/A |