$114+ 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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Apr 18 — Apr 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Oregon with Cheapflights
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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 March 19, 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 March 19, 2026.
This Frontier deal was found by Cheapflights users on 3/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:58 pm
ORD
- PDX
1 stop14h 01m
Frontier
Fri 5/85:31 pm
PDX
- ORD
1 stop11h 08m
Frontier
Deal found 3/14![Frontier logo]()
$210
This Mytrip deal was found by Cheapflights users on 3/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Sat 5/212:27 pm
PDX
- ORD
1 stop19h 18m
Frontier
Deal found 3/15![Frontier logo]()
$219
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/306:00 pm
ORD
- EUG
1 stop7h 58m
Delta
Wed 5/612:28 pm
EUG
- ORD
1 stop7h 17m
Delta
Deal found 3/19![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 10/203:50 pm
ORD
- EUG
2 stops9h 57m
Delta
Tue 10/276:15 am
EUG
- ORD
2 stops13h 38m
Delta
Deal found 3/19![Delta logo]()
$237
This Mytrip deal was found by Cheapflights users on 3/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Thu 5/75:31 pm
PDX
- ORD
1 stop11h 08m
Frontier
Deal found 3/15![Frontier logo]()
$237
This Gotogate deal was found by Cheapflights users on 3/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Mon 4/2712:45 pm
PDX
- ORD
1 stop15h 23m
Frontier
Deal found 3/15![Frontier logo]()
$239
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 5/149:42 pm
ORD
- PDX
1 stop21h 04m
Frontier
Mon 5/185:31 pm
PDX
- ORD
1 stop11h 08m
Frontier
Deal found 3/17![Frontier logo]()
$241
This CheapOair deal was found by Cheapflights users on 3/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:58 pm
ORD
- PDX
1 stop14h 01m
Frontier
Mon 5/49:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Deal found 3/14![Frontier logo]()
$242
This Booking.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Fri 4/1710:55 am
ORD
- PDX
1 stop26h 47m
Frontier
Sun 4/1911:15 am
PDX
- ORD
1 stop20h 35m
Frontier
Deal found 3/17![Frontier logo]()
$243
This Trip.com deal was found by Cheapflights users on 3/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Mon 4/279:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Deal found 3/15![Frontier logo]()
$245
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/148:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 4/215:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 3/17![Southwest logo]()
$251
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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.
Sat 4/1811:52 am
ORD
- PDX
Nonstop4h 32m
American Airlines
Sat 4/1811:47 pm
PDX
- ORD
Nonstop4h 02m
American Airlines
Deal found 3/19![American Airlines logo]()
$251
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 March 19, 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 March 19, 2026.
This Delta deal was found by Cheapflights users on 3/15. 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.
Fri 4/177:35 am
ORD
- EUG
1 stop6h 13m
Delta
Tue 4/216:30 am
EUG
- ORD
1 stop8h 09m
Delta
Deal found 3/15![Delta logo]()
$257
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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.
Sat 4/186:00 am
ORD
- EUG
1 stop8h 30m
Alaska Airlines
Tue 4/217:00 am
EUG
- ORD
1 stop9h 40m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 3/15. 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.
Fri 5/156:00 am
MDW
- EUG
1 stop6h 30m
Southwest
Sun 5/173:45 pm
EUG
- MDW
1 stop10h 50m
Southwest
Deal found 3/15![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/118:00 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Tue 4/1411:59 pm
PDX
- ORD
Nonstop4h 04m
United Airlines
Deal found 3/17![United Airlines logo]()
$299
This Alaska Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/83:52 pm
ORD
- EUG
1 stop9h 02m
Alaska Airlines
Mon 5/118:38 pm
EUG
- ORD
1 stop8h 02m
Alaska Airlines
Deal found 3/19![Alaska Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 3/15. 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.
Thu 4/306:00 am
MDW
- EUG
1 stop6h 30m
Southwest
Mon 5/45:00 pm
EUG
- MDW
1 stop10h 00m
Southwest
Deal found 3/15![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/1412:46 pm
ORD
- PDX
1 stop6h 24m
Delta
Tue 4/2110:55 pm
PDX
- ORD
1 stop7h 45m
Delta
Deal found 3/18![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/164:05 pm
MDW
- EUG
2 stops8h 40m
Southwest
Sat 4/186:00 am
EUG
- MDW
2 stops9h 15m
Southwest
Deal found 3/18![Southwest logo]()
$267
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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.
Sat 4/186:00 am
ORD
- BOI
1 stop7h 22m
Alaska Airlines
Sat 4/252:57 pm
BOI
- ORD
1 stop8h 02m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 3/14. 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.
Wed 6/37:55 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Sat 6/65:00 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Deal found 3/14![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 3/16. 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.
Sat 5/95:19 pm
ORD
- PDX
1 stop6h 43m
Delta
Sat 5/167:05 am
PDX
- ORD
1 stop8h 08m
Delta
Deal found 3/16![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 3/16. 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 5/123:40 pm
MDW
- PDX
1 stop7h 05m
Southwest
Sat 5/1611:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 3/16![Southwest logo]()
$277
This Alaska Airlines deal was found by Cheapflights users on 3/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
ORD
- RDM
1 stop8h 58m
Alaska Airlines
Sat 5/91:52 pm
RDM
- ORD
1 stop8h 07m
Alaska Airlines
Deal found 3/15![Alaska Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 3/15. 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.
Wed 4/2211:19 am
ORD
- PDX
1 stop9h 46m
Delta
Sat 4/2511:15 pm
PDX
- ORD
1 stop6h 46m
Delta
Deal found 3/15![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:07 pm
ORD
- PDX
Nonstop4h 35m
United Airlines
Sun 6/710:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 3/16![United Airlines logo]()
$327
This Alaska Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/177:24 pm
ORD
- EUG
1 stop6h 34m
Alaska Airlines
Sat 4/187:00 am
EUG
- ORD
1 stop10h 02m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$288
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 5/79:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 5/125:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 3/18![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/147:05 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Sun 6/1411:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Deal found 3/16![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 3/14. 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 5/157:45 pm
ORD
- MFR
1 stop5h 57m
Delta
Wed 5/2012:21 pm
MFR
- ORD
1 stop9h 36m
Delta
Deal found 3/14![Delta logo]()
$320
This Alaska Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/154:10 pm
ORD
- BOI
1 stop8h 37m
Alaska Airlines
Wed 4/222:57 pm
BOI
- ORD
1 stop8h 02m
Alaska Airlines
Deal found 3/17![Alaska Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 3/14. 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.
Fri 5/229:21 pm
ORD
- PDX
Nonstop4h 32m
United Airlines
Sun 5/244:15 pm
PDX
- ORD
1 stop6h 29m
United Airlines
Deal found 3/14![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 3/16. 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.
Sat 5/235:30 pm
MDW
- EUG
1 stop6h 10m
Southwest
Sun 5/313:45 pm
EUG
- MDW
2 stops11h 40m
Southwest
Deal found 3/16![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 3/15. 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.
Mon 5/117:45 pm
ORD
- MFR
1 stop5h 57m
Delta
Tue 5/1912:21 pm
MFR
- ORD
1 stop9h 36m
Delta
Deal found 3/15![Delta logo]()
$320
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 6/138:25 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 6/168:35 pm
PDX
- MDW
1 stop6h 35m
Southwest
Deal found 3/18![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/122:00 pm
ORD
- MFR
2 stops11h 55m
Delta
Wed 5/2012:21 pm
MFR
- ORD
1 stop9h 36m
Delta
Deal found 3/19![Delta logo]()
$322
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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.
Sat 4/116:00 am
ORD
- BOI
1 stop8h 58m
Alaska Airlines
Sat 4/1811:58 am
BOI
- ORD
1 stop11h 01m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 6/38:40 am
ORD
- BOI
Nonstop3h 52m
United Airlines
Sun 6/75:46 pm
BOI
- ORD
1 stop5h 58m
United Airlines
Deal found 3/19![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/198:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Sun 5/2411:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 3/19![Southwest logo]()
$316
This Delta deal was found by Cheapflights users on 3/14. 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 5/157:45 pm
ORD
- MFR
1 stop5h 57m
Delta
Tue 5/196:15 am
MFR
- ORD
2 stops13h 35m
Delta
Deal found 3/14![Delta logo]()
$325
This Alaska Airlines deal was found by Cheapflights users on 3/14. 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.
Thu 4/237:59 pm
ORD
- PDX
1 stop15h 49m
Alaska Airlines
Sat 4/258:45 am
PDX
- ORD
1 stop9h 07m
Alaska Airlines
Deal found 3/14![Alaska Airlines logo]()
$336
Last-minute flights from Chicago to OregonDiscover last-minute flight deals from Chicago to Oregon. Data last updated March 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Oregon. Data last updated March 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/87:20 am
ORD
- EUG
1 stop6h 40m
Delta
Fri 4/1012:40 pm
EUG
- ORD
1 stop6h 54m
Delta
Deal found 3/19![Delta logo]()
$256
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:29 pm
ORD
- PDX
1 stop24h 33m
Frontier
Fri 4/179:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Deal found 3/18![Frontier logo]()
$241
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/148:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Tue 4/215:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 3/17![Southwest logo]()
$251
This Booking.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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.
Fri 4/1710:55 am
ORD
- PDX
1 stop26h 47m
Frontier
Sun 4/1911:15 am
PDX
- ORD
1 stop20h 35m
Frontier
Deal found 3/17![Frontier logo]()
$243
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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.
Sat 4/1811:52 am
ORD
- PDX
Nonstop4h 32m
American Airlines
Sat 4/1811:47 pm
PDX
- ORD
Nonstop4h 02m
American Airlines
Deal found 3/19![American Airlines logo]()
$251
This Gotogate deal was found by Cheapflights users on 3/15. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Mon 4/2712:45 pm
PDX
- ORD
1 stop15h 23m
Frontier
Deal found 3/15![Frontier logo]()
$239
This Mytrip deal was found by Cheapflights users on 3/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Sat 5/212:27 pm
PDX
- ORD
1 stop19h 18m
Frontier
Deal found 3/15![Frontier logo]()
$219
This Trip.com deal was found by Cheapflights users on 3/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Mon 4/279:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Deal found 3/15![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 3/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:58 pm
ORD
- PDX
1 stop14h 01m
Frontier
Fri 5/85:31 pm
PDX
- ORD
1 stop11h 08m
Frontier
Deal found 3/14![Frontier logo]()
$210
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/306:00 pm
ORD
- EUG
1 stop7h 58m
Delta
Wed 5/612:28 pm
EUG
- ORD
1 stop7h 17m
Delta
Deal found 3/19![Delta logo]()
$227
This Mytrip deal was found by Cheapflights users on 3/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:21 pm
ORD
- PDX
1 stop18h 29m
Frontier
Thu 5/75:31 pm
PDX
- ORD
1 stop11h 08m
Frontier
Deal found 3/15![Frontier logo]()
$237
This CheapOair deal was found by Cheapflights users on 3/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:58 pm
ORD
- PDX
1 stop14h 01m
Frontier
Mon 5/49:54 am
PDX
- ORD
1 stop17h 56m
Frontier
Deal found 3/14![Frontier logo]()
$242
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 March 19, 2026.
Search for one-way flight options from Chicago to Oregon. Find affordable one-way fares based on user searches. Data last updated March 19, 2026.
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 6/136:00 pm
ORD
- EUG
1 stop7h 54m
Delta
Deal found 3/19![Delta logo]()
$114
This Gotogate deal was found by Cheapflights users on 3/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:29 pm
ORD
- BOI
1 stop20h 39m
Frontier
Deal found 3/14![Frontier logo]()
$115
This Booking.com deal was found by Cheapflights users on 3/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:53 pm
ORD
- BOI
1 stop18h 15m
Frontier
Deal found 3/14![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:44 pm
ORD
- PDX
2 stops38h 36m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:07 am
ORD
- PDX
2 stops26h 31m
Frontier
Deal found 3/14![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:40 am
ORD
- PDX
2 stops54h 58m
Frontier
Deal found 3/16![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:23 am
ORD
- PDX
2 stops25h 57m
Frontier
Deal found 3/16![Frontier logo]()
$124
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/148:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 3/19![Southwest logo]()
$126
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/229:10 am
ORD
- PDX
Nonstop4h 36m
United Airlines
Deal found 3/18![United Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:11 pm
MDW
- PDX
2 stops44h 27m
Frontier
Deal found 3/14![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/143:27 pm
ORD
- BOI
2 stops44h 41m
Frontier
Deal found 3/18![Frontier logo]()
$128
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” 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 4/67:20 am
ORD
- EUG
1 stop6h 40m
Delta
Deal found 3/17![Delta logo]()
$129
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 March 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $210 (Frontier) |
One-way from | $114 (Delta) |
Popular in | March |
Cheapest in | January |
Average price | $435 |
Good round-trip deal | $248 or less |
Good one-way deal | $133 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 March 19, 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
Fri 4/17
7:35 am-11:48 am
1 stop6h 13m
Eugene
Tue 4/21
6:30 am-4:39 pm
1 stop8h 09m
$257
ChicagoEugene
ORD - EUG
ORDEUG
Chicago O'Hare Intl
Sat 4/18
6:00 am-12:30 pm
1 stop8h 30m
Eugene
Tue 4/21
7:00 am-6:40 pm
1 stop9h 40m
$257
ChicagoEugene
ORD - EUG
ORDEUG
Chicago O'Hare Intl
Fri 5/8
3:52 pm-10:54 pm
1 stop9h 02m
Eugene
Mon 5/11
8:38 pm-6:40 am
1 stop8h 02m
$257
ChicagoEugene
MDW - EUG
MDWEUG
Chicago Midway
Fri 5/15
6:00 am-10:30 am
1 stop6h 30m
Eugene
Sun 5/17
3:45 pm-4:35 am
1 stop10h 50m
$262
ChicagoEugene
MDW - EUG
MDWEUG
Chicago Midway
Thu 4/30
6:00 am-10:30 am
1 stop6h 30m
Eugene
Mon 5/4
5:00 pm-5:00 am
1 stop10h 00m
$262
ChicagoEugene
MDW - EUG
MDWEUG
Chicago Midway
Thu 4/16
4:05 pm-10:45 pm
2 stops8h 40m
Eugene
Sat 4/18
6:00 am-5:15 pm
2 stops9h 15m
$267
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 4/14
12:46 pm-5:10 pm
1 stop6h 24m
Portland
Tue 4/21
10:55 pm-8:40 am
1 stop7h 45m
$271
ChicagoBoise
ORD - BOI
ORDBOI
Chicago O'Hare Intl
Sat 4/18
6:00 am-12:22 pm
1 stop7h 22m
Boise Air Term. Gowen Fld
Sat 4/25
2:57 pm-11:59 pm
1 stop8h 02m
$277
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 5/12
3:40 pm-8:45 pm
1 stop7h 05m
Portland
Sat 5/16
11:55 pm-5:50 am
Nonstop3h 55m
$277
ChicagoRedmond
ORD - RDM
ORDRDM
Chicago O'Hare Intl
Wed 5/6
6:00 am-12:58 pm
1 stop8h 58m
Bend/Redmond
Sat 5/9
1:52 pm-11:59 pm
1 stop8h 07m
$277
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
MDW-EUG
ORD-PDX
ORD-RDM
MDW-MFR
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
MDW-EUG
ORD-PDX
ORD-RDM
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 $133). Flying from Chicago to Oregon in December is currently the most expensive (average of $207). 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 March 19, 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 17% 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 March 14, 2026.
Travelers seeking maximum savings on their Chicago to Oregon flight should consider departing on Saturday mornings 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.
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 March 19, 2026.
The most flights from CHI to USOR are scheduled on a Wednesday (22 on average). You will have fewer flight options on Tuesday, 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?
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 March 19, 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.
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
8.0
Boarding
8.1
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 March 19, 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 March 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$178 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$124 | Average$366 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$139 | Average$398 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$232 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$464 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$194 | Average$404 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$201 | Average$313 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$227 | Average$383 | FlexibilityNo cancel fee | On-time63% |