$109+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
May 31 — Jun 71
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Oregon
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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 May 1, 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 May 1, 2026.
This Expedia deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:49 pm
ORD
- BOI
1 stop16h 14m
Multiple Airlines
Tue 6/91:25 pm
BOI
- ORD
1 stop6h 18m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$258
This Mytrip deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:37 pm
ORD
- PDX
1 stop21h 09m
Frontier
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/27![Frontier logo]()
$262
This Frontier deal was found by Cheapflights users on 4/27. 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 7/107:15 am
ORD
- PDX
1 stop12h 49m
Frontier
Sun 7/126:59 pm
PDX
- ORD
1 stop8h 29m
Frontier
Deal found 4/27![Frontier logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/239:37 pm
ORD
- PDX
2 stops16h 13m
Frontier
Tue 5/265:46 pm
PDX
- ORD
1 stop24h 46m
Frontier
Deal found 4/28![Frontier logo]()
$278
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:48 pm
ORD
- PDX
1 stop20h 47m
Multiple Airlines
Fri 6/1210:59 pm
PDX
- ORD
Nonstop4h 01m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/308:46 pm
ORD
- PDX
1 stop17h 04m
Frontier
Tue 6/25:46 pm
PDX
- ORD
2 stops24h 05m
Frontier
Deal found 4/28![Frontier logo]()
$281
This Super.com deal was found by Cheapflights users on 4/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:46 pm
ORD
- PDX
1 stop17h 04m
Frontier
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/28![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 5/289:37 pm
ORD
- PDX
2 stops40h 13m
Frontier
Tue 6/25:46 pm
PDX
- ORD
1 stop24h 46m
Frontier
Deal found 4/28![Frontier logo]()
$283
This Expedia deal was found by Cheapflights users on 4/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Sun 7/126:59 pm
PDX
- ORD
1 stop8h 29m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$288
This Expedia deal was found by Cheapflights users on 4/27. 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 7/27:20 am
ORD
- PDX
Nonstop4h 25m
Multiple Airlines
Mon 7/136:59 pm
PDX
- ORD
1 stop8h 29m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$289
This Frontier deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:12 am
ORD
- PDX
1 stop12h 12m
Frontier
Sat 6/275:42 pm
PDX
- ORD
1 stop10h 37m
Frontier
Deal found 4/30![Frontier logo]()
$290
This Travelocity deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity 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
Multiple Airlines
Tue 9/1512:59 pm
BOI
- ORD
1 stop7h 36m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$293
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 May 1, 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 May 1, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:40 am
ORD
- BOI
1 stop8h 54m
Alaska Airlines
Mon 6/16:12 pm
BOI
- ORD
1 stop18h 02m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 4/26. 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.
Thu 7/99:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Wed 7/1511:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 4/26![Southwest logo]()
$316
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 5/268:57 am
ORD
- PDX
Nonstop4h 41m
United Airlines
Tue 6/24:15 pm
PDX
- ORD
1 stop6h 29m
United Airlines
Deal found 4/28![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:06 pm
MDW
- BOI
1 stop5h 40m
Delta
Sat 7/255:30 am
BOI
- MDW
1 stop6h 39m
Delta
Deal found 4/29![Delta logo]()
$335
This Alaska Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 4/28. 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 5/284:10 pm
MDW
- PDX
1 stop7h 30m
Southwest
Mon 6/111:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 4/28![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 7/127:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Thu 7/165:00 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 4/29![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 am
ORD
- BOI
1 stop8h 13m
Delta
Sat 6/68:58 am
BOI
- ORD
2 stops11h 52m
Delta
Deal found 4/30![Delta logo]()
$340
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mon 6/89:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 6/168:35 pm
PDX
- MDW
1 stop6h 35m
Southwest
Deal found 4/27![Southwest logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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.
Thu 7/167:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/1910:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Sat 5/238:53 am
ORD
- EUG
Nonstop4h 44m
United Airlines
Sat 5/3012:57 pm
EUG
- ORD
1 stop7h 52m
United Airlines
Deal found 4/25![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:23 am
MDW
- BOI
2 stops9h 27m
Delta
Thu 5/289:16 pm
BOI
- MDW
2 stops10h 26m
Delta
Deal found 4/29![Delta logo]()
$345
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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 5/307:49 pm
ORD
- PDX
1 stop14h 13m
Alaska Airlines
Mon 6/17:15 am
PDX
- ORD
1 stop9h 35m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/129:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Mon 6/158:15 pm
PDX
- MDW
1 stop7h 30m
Southwest
Deal found 4/27![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 4/28. 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 6/252:45 pm
ORD
- PDX
1 stop9h 37m
Delta
Fri 6/269:45 am
PDX
- ORD
1 stop7h 13m
Delta
Deal found 4/28![Delta logo]()
$347
This United Airlines deal was found by Cheapflights users on 4/28. 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 5/216:00 am
ORD
- EUG
1 stop8h 57m
United Airlines
Tue 5/261:59 pm
EUG
- ORD
1 stop9h 00m
United Airlines
Deal found 4/28![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:40 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Mon 6/81:05 pm
PDX
- MDW
2 stops9h 30m
Southwest
Deal found 4/29![Southwest logo]()
$342
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 7/216:00 am
ORD
- EUG
1 stop9h 01m
Alaska Airlines
Tue 7/214:00 pm
EUG
- ORD
1 stop11h 00m
Alaska Airlines
Deal found 4/28![Alaska Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:13 pm
MDW
- BOI
1 stop5h 33m
Delta
Mon 6/111:39 pm
BOI
- MDW
1 stop9h 21m
Delta
Deal found 4/29![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:40 am
ORD
- BOI
Nonstop3h 52m
United Airlines
Sat 5/3012:38 pm
BOI
- ORD
Nonstop3h 34m
United Airlines
Deal found 4/30![United Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 4/28. 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.
Sat 6/272:35 pm
MDW
- PDX
1 stop7h 05m
Southwest
Sat 7/46:00 am
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 4/28![Southwest logo]()
$346
This Alaska Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:20 am
ORD
- EUG
1 stop9h 40m
Alaska Airlines
Mon 6/294:00 pm
EUG
- ORD
1 stop11h 00m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:36 am
ORD
- EUG
2 stops9h 29m
Delta
Mon 6/291:40 pm
EUG
- ORD
1 stop6h 17m
Delta
Deal found 4/26![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:12 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Mon 5/2510:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 4/28![United Airlines logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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.
Thu 5/286:00 am
ORD
- EUG
1 stop9h 08m
Alaska Airlines
Sat 5/307:59 pm
EUG
- ORD
1 stop8h 21m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:55 am
ORD
- BOI
1 stop9h 17m
Delta
Mon 6/291:05 pm
BOI
- ORD
1 stop7h 52m
Delta
Deal found 4/30![Delta logo]()
$355
This Southwest deal was found by Cheapflights users on 4/27. 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.
Mon 6/82:30 pm
MDW
- PDX
1 stop7h 30m
Southwest
Thu 6/1111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 4/27![Southwest logo]()
$357
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:00 am
ORD
- BOI
1 stop5h 45m
United Airlines
Sun 6/285:46 pm
BOI
- ORD
1 stop5h 58m
United Airlines
Deal found 4/30![United Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 4/26. 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 6/239:54 am
MDW
- BOI
2 stops8h 58m
Delta
Mon 6/295:30 am
BOI
- MDW
1 stop6h 39m
Delta
Deal found 4/26![Delta logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Sun 7/2610:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Deal found 4/30![Alaska Airlines logo]()
$362
Last-minute flights from Chicago to OregonDiscover last-minute flight deals from Chicago to Oregon. Data last updated May 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oregon. Data last updated May 1, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:56 pm
ORD
- PDX
1 stop16h 54m
Frontier
Sun 5/315:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/30![Frontier logo]()
$288
This Gotogate deal was found by Cheapflights users on 4/26. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:37 pm
ORD
- PDX
1 stop21h 09m
Frontier
Sun 5/245:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/26![Frontier logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/239:37 pm
ORD
- PDX
2 stops16h 13m
Frontier
Tue 5/265:46 pm
PDX
- ORD
1 stop24h 46m
Frontier
Deal found 4/28![Frontier logo]()
$278
This Super.com deal was found by Cheapflights users on 4/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:46 pm
ORD
- PDX
1 stop17h 04m
Frontier
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/28![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/239:37 pm
ORD
- PDX
2 stops16h 13m
Frontier
Mon 5/2512:35 pm
PDX
- ORD
1 stop29h 57m
Frontier
Deal found 4/28![Frontier logo]()
$289
This Expedia deal was found by Cheapflights users on 4/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/232:18 pm
ORD
- PDX
Nonstop4h 32m
Multiple Airlines
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$294
This Mytrip deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:37 pm
ORD
- PDX
1 stop21h 09m
Frontier
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Frontier
Deal found 4/27![Frontier logo]()
$262
This Orbitz deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:00 am
ORD
- PDX
1 stop9h 58m
Multiple Airlines
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$291
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Wed 5/275:44 pm
ORD
- BOI
1 stop7h 14m
Alaska Airlines
Wed 6/36:35 am
BOI
- ORD
1 stop9h 13m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$295
This Expedia deal was found by Cheapflights users on 4/27. 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 5/282:18 pm
ORD
- PDX
Nonstop4h 32m
Multiple Airlines
Sat 5/305:31 pm
PDX
- ORD
1 stop11h 03m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 4/28. 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 5/289:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 6/211:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 4/28![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 5/308:46 pm
ORD
- PDX
1 stop17h 04m
Frontier
Tue 6/25:46 pm
PDX
- ORD
2 stops24h 05m
Frontier
Deal found 4/28![Frontier logo]()
$281
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 May 1, 2026.
Search for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated May 1, 2026.
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:37 pm
ORD
- BOI
1 stop15h 50m
Frontier
Deal found 4/29![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/279:37 pm
ORD
- BOI
1 stop15h 53m
Frontier
Deal found 4/29![Frontier logo]()
$112
This CheapOair deal was found by Cheapflights users on 4/29. 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 7/189:57 pm
ORD
- BOI
1 stop15h 32m
Frontier
Deal found 4/29![Frontier logo]()
$131
This Trip.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:37 pm
ORD
- BOI
1 stop15h 50m
Frontier
Deal found 4/27![Frontier logo]()
$134
This CheapOair deal was found by Cheapflights users on 4/27. 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 6/109:48 pm
ORD
- BOI
1 stop15h 42m
Frontier
Deal found 4/27![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 6/229:48 pm
ORD
- BOI
1 stop15h 42m
Frontier
Deal found 4/27![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/239:37 pm
ORD
- BOI
1 stop15h 53m
Frontier
Deal found 4/29![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Fri 6/53:07 pm
MDW
- PDX
2 stops27h 39m
Frontier
Deal found 4/27![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sun 7/198:11 pm
MDW
- PDX
1 stop17h 19m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Sat 6/279:48 pm
ORD
- BOI
1 stop15h 42m
Frontier
Deal found 4/27![Frontier logo]()
$145
This Super.com deal was found by Cheapflights users on 4/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:10 pm
ORD
- PDX
1 stop13h 49m
Frontier
Deal found 4/28![Frontier logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Tue 5/194:06 pm
ORD
- PDX
2 stops44h 14m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$148
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 May 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $258 (Expedia) |
One-way from | $109 (Trip.com) |
Popular in | March |
Cheapest in | January |
Average price | $274 |
Good round-trip deal | $316 or less |
Good one-way deal | $152 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 May 1, 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
Thu 5/28
7:40 am-3:34 pm
1 stop8h 54m
Boise Air Term. Gowen Fld
Mon 6/1
6:12 pm-1:14 pm
1 stop18h 02m
$310
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 7/9
9:35 pm-11:55 pm
Nonstop4h 20m
Portland
Wed 7/15
11:30 pm-5:20 am
Nonstop3h 50m
$316
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 7/22
7:20 am-9:45 am
Nonstop4h 25m
Portland
Sun 7/26
10:59 pm-5:00 am
Nonstop4h 01m
$316
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 5/26
8:57 am-11:38 am
Nonstop4h 41m
Portland
Tue 6/2
4:15 pm-12:44 am
1 stop6h 29m
$326
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 5/28
4:10 pm-9:40 pm
1 stop7h 30m
Portland
Mon 6/1
11:55 pm-5:50 am
Nonstop3h 55m
$326
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Mon 6/8
9:35 pm-11:55 pm
Nonstop4h 20m
Portland
Tue 6/16
8:35 pm-5:10 am
1 stop6h 35m
$326
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sun 7/12
7:00 am-9:34 am
Nonstop4h 34m
Portland
Thu 7/16
5:00 pm-11:13 pm
Nonstop4h 13m
$327
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Thu 7/16
7:20 am-9:45 am
Nonstop4h 25m
Portland
Sun 7/19
10:59 pm-5:00 am
Nonstop4h 01m
$327
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Tue 7/21
7:06 pm-11:46 pm
1 stop5h 40m
Boise Air Term. Gowen Fld
Sat 7/25
5:30 am-1:09 pm
1 stop6h 39m
$335
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Sat 5/30
7:49 pm-8:02 am
1 stop14h 13m
Portland
Mon 6/1
7:15 am-6:50 pm
1 stop9h 35m
$336
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-PDX
ORD-PDX
ORD-EUG
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-BOI
MDW-PDX
ORD-PDX
ORD-EUG
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 77 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 month to book a flight from Chicago to Oregon?
Currently, September is the cheapest month in which you can book a flight from Chicago to Oregon (average of $105). Flying from Chicago to Oregon in October is currently the most expensive (average of $846). 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 May 1, 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 18% on airfare.
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 April 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 1, 2026.
The most flights from CHI to USOR are scheduled on a Thursday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).
How much does it cost to fly round-trip from Chicago to Oregon?
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 May 1, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andHawaiian Airlines 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
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Oregon
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Oregon by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Oregon by cabin class
Find flights from Chicago to Oregon, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Oregon flights
Browse other Chicago and Oregon flight options. Last updated on May 1, 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 May 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$178 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$124 | Average$353 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$139 | Average$411 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$248 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$190 | Average$420 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$197 | Average$562 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$198 | Average$458 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$227 | Average$383 | FlexibilityNo cancel fee | On-time63% |