$117+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Jul 17 — Jul 241
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oregon with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to OregonExplore the most affordable flight options available from Chicago to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 17, 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 June 17, 2026.
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- EUG
1 stop8h 04m
Delta
Sat 7/412:32 pm
EUG
- ORD
1 stop9h 07m
Delta
Deal found 6/12![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:35 pm
ORD
- EUG
2 stops12h 19m
Delta
Tue 9/156:10 am
EUG
- ORD
2 stops10h 09m
Delta
Deal found 6/12![Delta logo]()
$307
This CheapOair deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/209:48 pm
ORD
- PDX
1 stop21h 09m
Frontier
Tue 8/255:42 pm
PDX
- ORD
1 stop25h 11m
Frontier
Deal found 6/16![Frontier logo]()
$308
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/149:57 pm
ORD
- PDX
1 stop20h 39m
Frontier
Sat 8/85:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Deal found 6/16![Frontier logo]()
$309
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Wed 7/225:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Deal found 6/16![Frontier logo]()
$310
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/287:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Fri 7/315:49 pm
PDX
- ORD
1 stop9h 48m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$311
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/137:15 am
ORD
- PDX
1 stop12h 49m
Frontier
Sun 8/235:42 pm
PDX
- ORD
1 stop10h 37m
Frontier
Deal found 6/16![Frontier logo]()
$312
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/237:15 am
ORD
- PDX
1 stop12h 49m
Frontier
Mon 7/275:49 pm
PDX
- ORD
1 stop9h 48m
Frontier
Deal found 6/16![Frontier logo]()
$313
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Mon 7/67:15 am
ORD
- PDX
1 stop11h 39m
Frontier
Mon 7/135:49 pm
PDX
- ORD
1 stop9h 48m
Frontier
Deal found 6/16![Frontier logo]()
$314
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/289:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Tue 8/411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 6/16![Southwest logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/87:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sat 8/1510:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$315
This Expedia deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 7/187:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Thu 7/235:36 pm
PDX
- ORD
1 stop10h 41m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$316
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 June 17, 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 June 17, 2026.
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:48 am
ORD
- EUG
2 stops11h 15m
Delta
Thu 8/271:44 pm
EUG
- ORD
1 stop5h 46m
Delta
Deal found 6/12![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Sat 8/811:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 6/14![United Airlines logo]()
$315
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:50 am
MDW
- PDX
2 stops10h 35m
Southwest
Wed 8/1211:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 6/12![Southwest logo]()
$330
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/285:42 pm
ORD
- PDX
1 stop7h 53m
Alaska Airlines
Sat 8/110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/311:30 am
ORD
- BOI
Nonstop3h 50m
American Airlines
Sat 7/113:12 pm
BOI
- ORD
Nonstop3h 52m
American Airlines
Deal found 6/16![American Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/285:30 am
MDW
- PDX
1 stop6h 15m
Southwest
Tue 8/410:45 pm
PDX
- MDW
1 stop8h 15m
Southwest
Deal found 6/16![Southwest logo]()
$335
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:56 am
MDW
- PDX
1 stop9h 59m
Delta
Mon 9/712:25 am
PDX
- MDW
1 stop6h 23m
Delta
Deal found 6/14![Delta logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/258:20 pm
ORD
- PDX
1 stop13h 17m
Alaska Airlines
Sat 8/110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$335
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
ORD
- PDX
Nonstop4h 29m
United Airlines
Thu 8/272:27 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 6/12![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:36 pm
ORD
- PDX
1 stop9h 36m
Delta
Mon 8/2412:35 am
PDX
- ORD
1 stop5h 55m
Delta
Deal found 6/14![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/136:30 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Tue 8/186:25 pm
PDX
- MDW
1 stop9h 20m
Southwest
Deal found 6/16![Southwest logo]()
$336
This United Airlines deal was found by Cheapflights users on 6/12. 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 8/67:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Sun 8/911:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 6/12![United Airlines logo]()
$337
This Alaska Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:20 pm
ORD
- PDX
1 stop13h 17m
Alaska Airlines
Sun 7/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:00 pm
MDW
- PDX
2 stops9h 50m
Southwest
Mon 8/1711:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 6/12![Southwest logo]()
$341
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:00 am
ORD
- MFR
1 stop9h 47m
American Airlines
Sat 8/223:40 pm
MFR
- ORD
1 stop6h 48m
American Airlines
Deal found 6/16![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/271:50 pm
ORD
- PDX
1 stop9h 54m
Delta
Tue 9/15:30 am
PDX
- ORD
1 stop5h 53m
Delta
Deal found 6/16![Delta logo]()
$346
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORD
- EUG
1 stop7h 43m
United Airlines
Tue 8/251:57 pm
EUG
- ORD
1 stop9h 02m
United Airlines
Deal found 6/12![United Airlines logo]()
$349
This Expedia deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/38:20 pm
ORD
- BOI
1 stop14h 20m
Alaska Airlines
Sat 7/117:57 am
BOI
- ORD
1 stop10h 40m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:55 pm
MDW
- BOI
1 stop6h 40m
Southwest
Tue 7/216:00 am
BOI
- MDW
1 stop6h 25m
Southwest
Deal found 6/13![Southwest logo]()
$345
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/151:51 pm
MDW
- BOI
2 stops9h 55m
Delta
Wed 8/191:59 pm
BOI
- MDW
1 stop7h 37m
Delta
Deal found 6/15![Delta logo]()
$350
This Alaska Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
ORD
- BOI
1 stop7h 36m
Alaska Airlines
Mon 8/317:20 am
BOI
- ORD
1 stop11h 01m
Alaska Airlines
Deal found 6/14![Alaska Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/128:53 am
ORD
- EUG
Nonstop4h 44m
United Airlines
Sun 7/1912:50 pm
EUG
- ORD
Nonstop4h 10m
United Airlines
Deal found 6/14![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/56:50 am
MDW
- PDX
2 stops10h 35m
Southwest
Sat 8/81:35 pm
PDX
- MDW
2 stops12h 55m
Southwest
Deal found 6/15![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:59 pm
ORD
- EUG
2 stops12h 00m
Delta
Sun 8/301:44 pm
EUG
- ORD
1 stop5h 46m
Delta
Deal found 6/14![Delta logo]()
$354
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:20 pm
ORD
- RDM
1 stop14h 44m
Alaska Airlines
Tue 8/117:28 am
RDM
- ORD
1 stop9h 29m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 6/12. 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 7/118:40 am
ORD
- BOI
Nonstop3h 52m
United Airlines
Tue 7/145:46 pm
BOI
- ORD
1 stop5h 58m
United Airlines
Deal found 6/12![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/1910:10 am
MDW
- PDX
2 stops10h 05m
Southwest
Mon 8/247:00 pm
PDX
- MDW
1 stop8h 40m
Southwest
Deal found 6/16![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/151:51 pm
MDW
- BOI
1 stop8h 01m
Delta
Sat 8/225:30 am
BOI
- MDW
1 stop6h 40m
Delta
Deal found 6/12![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 6/12. 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 8/206:00 am
ORD
- EUG
1 stop7h 43m
United Airlines
Thu 8/272:19 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Deal found 6/12![United Airlines logo]()
$384
This Alaska Airlines deal was found by Cheapflights users on 6/12. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:42 pm
ORD
- BOI
1 stop7h 22m
Alaska Airlines
Sun 8/165:57 am
BOI
- ORD
1 stop6h 16m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$390
Last-minute flights from Chicago to OregonDiscover last-minute flight deals from Chicago to Oregon. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oregon. Data last updated June 17, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:55 am
ORD
- EUG
1 stop8h 04m
Delta
Sat 7/412:32 pm
EUG
- ORD
1 stop9h 07m
Delta
Deal found 6/12![Delta logo]()
$297
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Mon 7/67:15 am
ORD
- PDX
1 stop11h 39m
Frontier
Mon 7/135:49 pm
PDX
- ORD
1 stop9h 48m
Frontier
Deal found 6/16![Frontier logo]()
$314
This Expedia deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/107:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Sat 7/1812:20 pm
PDX
- ORD
1 stop6h 32m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$312
This Expedia deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/107:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Fri 7/175:36 pm
PDX
- ORD
1 stop10h 41m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$318
This Booking.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/149:57 pm
ORD
- PDX
1 stop20h 39m
Frontier
Sat 8/85:36 pm
PDX
- ORD
1 stop10h 41m
Frontier
Deal found 6/16![Frontier logo]()
$309
This Super.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:13 pm
ORD
- PDX
1 stop16h 22m
Frontier
Wed 7/225:21 pm
PDX
- ORD
1 stop25h 31m
Frontier
Deal found 6/16![Frontier logo]()
$310
This Expedia deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 7/187:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Thu 7/235:36 pm
PDX
- ORD
1 stop10h 41m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$316
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/237:15 am
ORD
- PDX
1 stop12h 49m
Frontier
Mon 7/275:49 pm
PDX
- ORD
1 stop9h 48m
Frontier
Deal found 6/16![Frontier logo]()
$313
This Priceline deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Tue 7/287:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Fri 7/315:49 pm
PDX
- ORD
1 stop9h 48m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$311
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/289:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Tue 8/411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 6/16![Southwest logo]()
$315
This Alaska Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/287:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Wed 7/2910:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/16![Alaska Airlines logo]()
$315
This Jettzy deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Fri 8/710:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$317
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 June 17, 2026.
Search for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated June 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:06 am
ORD
- BOI
1 stop25h 58m
Frontier
Deal found 6/12![Frontier logo]()
$117
This Frontier deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/106:50 am
ORD
- BOI
1 stop9h 07m
Frontier
Deal found 6/15![Frontier logo]()
$133
This CheapOair deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 7/159:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Deal found 6/15![Frontier logo]()
$134
This CheapOair deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/129:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Deal found 6/15![Frontier logo]()
$136
This Expedia deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
Sun 9/131:02 pm
ORD
- BOI
1 stop26h 55m
Frontier
Deal found 6/15![Frontier logo]()
$139
This Mundotrip deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mundotrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Deal found 6/15![Frontier logo]()
$144
This Flightnetwork deal was found by Cheapflights users on 6/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Deal found 6/12![Frontier logo]()
$147
This Delta deal was found by Cheapflights users on 6/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/267:37 pm
ORD
- EUG
1 stop6h 21m
Delta
Deal found 6/12![Delta logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:45 pm
MDW
- BOI
2 stops20h 44m
Frontier
Deal found 6/12![Frontier logo]()
$149
This Trip.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 6/209:48 pm
ORD
- BOI
1 stop15h 42m
Frontier
Deal found 6/16![Frontier logo]()
$151
This Trip.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Wed 6/249:48 pm
ORD
- BOI
1 stop15h 42m
Frontier
Deal found 6/16![Frontier logo]()
$152
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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.
Sat 9/1211:06 am
ORD
- PDX
1 stop7h 29m
Frontier
Deal found 6/16![Frontier logo]()
$153
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $297 (Delta) |
One-way from | $117 (Kiwi.com) |
Popular in | March |
Cheapest in | January |
Average price | $366 |
Good round-trip deal | $315 or less |
Good one-way deal | $173 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 June 17, 2026.
Use the filters below to find and compare flights from Chicago to Oregon that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoEugene
ORD - EUG
ORDEUG
Chicago O'Hare Intl
Thu 8/20
7:48 am-5:03 pm
2 stops11h 15m
Eugene
Thu 8/27
1:44 pm-9:30 pm
1 stop5h 46m
$302
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 8/1
7:00 am-9:34 am
Nonstop4h 34m
Portland
Sat 8/8
11:40 pm-5:45 am
Nonstop4h 05m
$315
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 8/12
6:50 am-3:25 pm
2 stops10h 35m
Portland
Wed 8/12
11:30 pm-5:25 am
Nonstop3h 55m
$330
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 7/28
5:42 pm-11:35 pm
1 stop7h 53m
Portland
Sat 8/1
10:59 pm-5:00 am
Nonstop4h 01m
$335
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 7/28
5:30 am-9:45 am
1 stop6h 15m
Portland
Tue 8/4
10:45 pm-9:00 am
1 stop8h 15m
$335
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 9/5
10:56 am-6:55 pm
1 stop9h 59m
Portland
Mon 9/7
12:25 am-8:48 am
1 stop6h 23m
$335
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 7/25
8:20 pm-7:37 am
1 stop13h 17m
Portland
Sat 8/1
10:59 pm-5:00 am
Nonstop4h 01m
$335
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 8/18
2:36 pm-10:12 pm
1 stop9h 36m
Portland
Mon 8/24
12:35 am-8:30 am
1 stop5h 55m
$335
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 8/13
6:30 pm-8:45 pm
Nonstop4h 15m
Portland
Tue 8/18
6:25 pm-5:45 am
1 stop9h 20m
$336
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 8/14
7:00 am-9:29 am
Nonstop4h 29m
Portland
Thu 8/27
2:27 pm-8:40 pm
Nonstop4h 13m
$337
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Oregon
Have a flexible travel schedule? Discover the best time to fly to Oregon from Chicago with our price prediction graph.
ORD-EUG
ORD-PDX
MDW-PDX
ORD-BOI
ORD-RDM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Oregon
CHI-USOR
ORD-EUG
ORD-PDX
MDW-PDX
ORD-BOI
What is the cheapest month to book a flight from Chicago to Oregon?
Currently, May is the cheapest month in which you can book a flight from Chicago to Oregon (average of $115). Flying from Chicago to Oregon in October is currently the most expensive (average of $816). 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 June 17, 2026.
One of the essential ways to save on airfare from Chicago to Oregon is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 10% 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 June 17, 2026.
The most flights from CHI to USOR are scheduled on a Monday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Chicago to Oregon?
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 June 13, 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. Sunday 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 June 17, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Southwest, andDelta from Chicago to Oregon by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Boarding
8.1
Overall
7.9
Crew
8.5
Entertainment
7.0
Comfort
7.8
Food
7.1
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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 June 17, 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 8 airlines flying from Chicago to Oregon
Discover the top 8 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 June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$238 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$150 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$159 | Average$436 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$196 | Average$447 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$201 | Average$572 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$204 | Average$450 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$372 | FlexibilityNo cancel fee | On-time63% |