$114+ Cheap flights from Oregon to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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Find cheap flights from Oregon to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Oregon to ChicagoExplore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2026.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:30 pm
EUG
- ORD
1 stop9h 16m
Delta
Mon 11/2312:40 pm
ORD
- EUG
1 stop6h 33m
Delta
Deal found 6/11![Delta logo]()
$297
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:15 am
EUG
- ORD
2 stops9h 42m
Delta
Tue 11/2412:40 pm
ORD
- EUG
1 stop6h 33m
Delta
Deal found 6/11![Delta logo]()
$302
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:10 am
EUG
- ORD
2 stops13h 20m
Delta
Mon 8/248:28 am
ORD
- EUG
2 stops9h 35m
Delta
Deal found 6/11![Delta logo]()
$307
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.
Mon 8/315:20 am
EUG
- MDW
2 stops10h 41m
Delta
Wed 9/92:00 pm
MDW
- EUG
2 stops10h 51m
Delta
Deal found 6/12![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:50 pm
EUG
- ORD
Nonstop4h 10m
United Airlines
Sun 7/58:53 am
ORD
- EUG
Nonstop4h 44m
United Airlines
Deal found 6/11![United Airlines logo]()
$309
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.
Tue 7/145:55 pm
EUG
- MDW
1 stop9h 05m
Southwest
Tue 7/216:10 am
MDW
- EUG
1 stop9h 55m
Southwest
Deal found 6/15![Southwest logo]()
$313
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.
Tue 9/15:42 pm
PDX
- ORD
1 stop25h 11m
Frontier
Wed 9/3010:40 pm
ORD
- PDX
1 stop19h 55m
Frontier
Deal found 6/12![Frontier logo]()
$317
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:42 pm
PDX
- ORD
1 stop25h 11m
Multiple Airlines
Wed 8/262:22 pm
ORD
- PDX
Nonstop4h 28m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:20 am
PDX
- ORD
1 stop9h 20m
Delta
Sun 8/236:00 am
ORD
- PDX
1 stop6h 41m
Delta
Deal found 6/11![Delta logo]()
$319
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.
Mon 7/612:50 pm
EUG
- ORD
Nonstop4h 10m
United Airlines
Sat 7/119:00 am
ORD
- EUG
Nonstop4h 44m
United Airlines
Deal found 6/14![United Airlines logo]()
$319
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 8/2611:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 8/306:10 am
MDW
- PDX
2 stops9h 10m
Southwest
Deal found 6/12![Southwest logo]()
$319
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1811:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Sat 7/258:25 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/14![Southwest logo]()
$320
Best flights from Oregon to ChicagoDiscover carefully curated flight deals from Oregon to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 2026.
Discover carefully curated flight deals from Oregon to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 16, 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.
Mon 8/315:20 am
EUG
- MDW
2 stops10h 41m
Delta
Wed 9/92:00 pm
MDW
- EUG
2 stops10h 51m
Delta
Deal found 6/12![Delta logo]()
$307
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.
Wed 8/510:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Tue 8/188:20 pm
ORD
- PDX
1 stop13h 51m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$325
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/114:05 pm
PDX
- ORD
1 stop5h 54m
United Airlines
Tue 8/187:00 am
ORD
- PDX
Nonstop4h 29m
United Airlines
Deal found 6/13![United Airlines logo]()
$325
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.
Tue 9/15:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Tue 9/88:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/15![Southwest logo]()
$331
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 7/1810:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Mon 7/207:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 6/12![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2012:31 pm
EUG
- ORD
1 stop9h 16m
Delta
Thu 10/12:05 pm
ORD
- EUG
2 stops11h 49m
Delta
Deal found 6/11![Delta logo]()
$328
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.
Tue 7/217:57 am
BOI
- ORD
1 stop10h 00m
Alaska Airlines
Tue 7/218:20 pm
ORD
- BOI
1 stop14h 20m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$335
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 9/21:25 pm
PDX
- MDW
1 stop7h 25m
Southwest
Sun 9/68:35 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/15![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 10/82:15 pm
EUG
- ORD
Nonstop4h 11m
United Airlines
Mon 10/129:05 am
ORD
- EUG
Nonstop4h 45m
United Airlines
Deal found 6/12![United Airlines logo]()
$329
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.
Wed 9/25:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Mon 9/78:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/13![Southwest logo]()
$337
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.
Thu 7/166:30 am
PDX
- ORD
1 stop9h 05m
Delta
Tue 7/217:40 pm
ORD
- PDX
1 stop6h 04m
Delta
Deal found 6/15![Delta logo]()
$346
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:08 am
EUG
- ORD
1 stop10h 13m
Alaska Airlines
Tue 9/152:18 pm
ORD
- EUG
1 stop8h 06m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$349
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.
Fri 9/252:27 pm
PDX
- ORD
Nonstop4h 13m
United Airlines
Sat 10/38:40 am
ORD
- PDX
1 stop7h 46m
United Airlines
Deal found 6/14![United Airlines logo]()
$336
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 7/285:55 pm
PDX
- MDW
1 stop9h 30m
Southwest
Tue 8/410:10 am
MDW
- PDX
2 stops10h 05m
Southwest
Deal found 6/13![Southwest logo]()
$340
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:34 pm
EUG
- ORD
1 stop14h 26m
Alaska Airlines
Tue 8/46:00 am
ORD
- EUG
1 stop9h 01m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$349
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:59 am
BOI
- ORD
2 stops11h 31m
Delta
Wed 8/197:44 pm
ORD
- BOI
1 stop5h 15m
Delta
Deal found 6/13![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Sun 8/27:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 6/11![United Airlines logo]()
$337
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
BOI
- MDW
1 stop6h 35m
Southwest
Tue 8/1810:20 am
MDW
- BOI
1 stop6h 50m
Southwest
Deal found 6/11![Southwest logo]()
$345
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 8/134:00 pm
EUG
- ORD
1 stop11h 00m
Alaska Airlines
Mon 8/175:42 pm
ORD
- EUG
1 stop8h 17m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$349
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.
Tue 7/141:40 pm
EUG
- ORD
1 stop5h 49m
Delta
Tue 7/217:45 am
ORD
- EUG
2 stops11h 20m
Delta
Deal found 6/15![Delta logo]()
$354
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.
Thu 8/2011:02 pm
PDX
- ORD
Nonstop4h 01m
United Airlines
Sun 8/238:50 am
ORD
- PDX
Nonstop4h 38m
United Airlines
Deal found 6/14![United Airlines logo]()
$337
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.
Sat 8/811:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 8/156:00 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/15![Southwest logo]()
$346
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.
Mon 9/1412:31 pm
EUG
- ORD
1 stop9h 16m
Delta
Sat 9/192:05 pm
ORD
- EUG
2 stops11h 49m
Delta
Deal found 6/14![Delta logo]()
$354
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.
Tue 7/287:32 am
PDX
- ORD
1 stop9h 25m
Alaska Airlines
Tue 8/48:20 pm
ORD
- PDX
1 stop13h 17m
Alaska Airlines
Deal found 6/13![Alaska Airlines logo]()
$356
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 7/1211:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Wed 7/157:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 6/14![United Airlines logo]()
$346
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.
Thu 10/12:35 pm
PDX
- MDW
1 stop5h 25m
Southwest
Sun 10/410:30 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 6/15![Southwest logo]()
$347
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:29 pm
EUG
- ORD
1 stop9h 00m
Delta
Mon 8/248:28 am
ORD
- EUG
2 stops9h 35m
Delta
Deal found 6/13![Delta logo]()
$354
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:05 pm
PDX
- MDW
1 stop7h 15m
Southwest
Mon 8/1710:40 am
MDW
- PDX
Nonstop4h 10m
Southwest
Deal found 6/14![Southwest logo]()
$347
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:40 pm
PDX
- ORD
Nonstop4h 05m
United Airlines
Tue 7/77:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 6/15![United Airlines logo]()
$348
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:07 am
RDM
- ORD
1 stop10h 14m
Alaska Airlines
Mon 9/147:00 pm
ORD
- RDM
1 stop6h 58m
Alaska Airlines
Deal found 6/15![Alaska Airlines logo]()
$389
Last-minute flights from Oregon to ChicagoDiscover last-minute flight deals from Oregon to Chicago. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Chicago. Data last updated June 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:15 am
PDX
- ORD
Nonstop4h 06m
American Airlines
Fri 8/149:30 pm
ORD
- PDX
Nonstop4h 29m
American Airlines
Deal found 6/11![American Airlines logo]()
$323
This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:50 pm
EUG
- ORD
Nonstop4h 10m
United Airlines
Sun 7/58:53 am
ORD
- EUG
Nonstop4h 44m
United Airlines
Deal found 6/11![United Airlines logo]()
$309
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.
Mon 7/612:50 pm
EUG
- ORD
Nonstop4h 10m
United Airlines
Sat 7/119:00 am
ORD
- EUG
Nonstop4h 44m
United Airlines
Deal found 6/14![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:32 pm
EUG
- ORD
1 stop9h 06m
Delta
Sun 7/126:55 am
ORD
- EUG
1 stop8h 03m
Delta
Deal found 6/11![Delta logo]()
$323
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Sat 7/117:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$326
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1110:59 pm
PDX
- ORD
Nonstop4h 01m
Alaska Airlines
Sun 7/127:20 am
ORD
- PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1412:32 pm
EUG
- ORD
1 stop9h 06m
Delta
Fri 7/177:40 pm
ORD
- EUG
1 stop6h 15m
Delta
Deal found 6/11![Delta logo]()
$297
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.
Tue 7/145:55 pm
EUG
- MDW
1 stop9h 05m
Southwest
Tue 7/216:10 am
MDW
- EUG
1 stop9h 55m
Southwest
Deal found 6/15![Southwest logo]()
$313
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.
Tue 7/1411:16 am
PDX
- ORD
1 stop7h 47m
United Airlines
Wed 7/227:00 am
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 6/12![United Airlines logo]()
$325
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1811:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Sat 7/258:25 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/14![Southwest logo]()
$320
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.
Tue 7/2111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 7/285:30 am
MDW
- PDX
1 stop6h 15m
Southwest
Deal found 6/15![Southwest logo]()
$325
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:20 pm
PDX
- ORD
1 stop6h 32m
Frontier
Tue 8/49:57 pm
ORD
- PDX
1 stop20h 39m
Frontier
Deal found 6/14![Frontier logo]()
$322
One-way flights from Oregon to ChicagoSearch for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
Search for one-way flight options from Oregon to Chicago. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:06 pm
BOI
- ORD
1 stop7h 24m
Delta
Deal found 6/11![Delta logo]()
$114
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:24 pm
BOI
- ORD
1 stop6h 28m
Frontier
Deal found 6/13![Frontier logo]()
$125
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:58 pm
BOI
- ORD
Nonstop3h 51m
American Airlines
Deal found 6/11![American Airlines logo]()
$126
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 8/131:24 pm
BOI
- ORD
1 stop6h 28m
Frontier
Deal found 6/15![Frontier logo]()
$133
This Frontier deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:24 pm
BOI
- ORD
1 stop6h 28m
Frontier
Deal found 6/11![Frontier logo]()
$135
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 9/133:52 pm
BOI
- ORD
1 stop12h 50m
Frontier
Deal found 6/15![Frontier logo]()
$139
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.
Tue 8/111:24 pm
BOI
- MDW
2 stops25h 26m
Frontier
Deal found 6/12![Frontier logo]()
$140
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.
Fri 9/113:52 pm
BOI
- ORD
1 stop12h 50m
Frontier
Deal found 6/15![Frontier logo]()
$140
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.
Tue 9/81:04 pm
BOI
- MDW
2 stops46h 03m
Frontier
Deal found 6/12![Frontier logo]()
$147
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:10 pm
BOI
- MDW
Nonstop3h 20m
Southwest
Deal found 6/11![Southwest logo]()
$149
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:59 pm
BOI
- ORD
1 stop7h 36m
Frontier
Deal found 6/12![Frontier logo]()
$149
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:38 pm
EUG
- ORD
1 stop6h 09m
Delta
Deal found 6/11![Delta logo]()
$149
Find flight deals from Oregon to Chicago
Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated June 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $278 (Southwest) |
One-way from | $114 (Delta) |
Popular in | November |
Cheapest in | January |
Average price | $384 |
Good round-trip deal | $390 or less |
Good one-way deal | $216 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 16, 2026.
Use the filters below to find and compare flights from Oregon to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
EugeneChicago
EUG - MDW
EUGMDW
Eugene
Mon 8/31
5:20 am-6:01 pm
2 stops10h 41m
Chicago Midway
Wed 9/9
2:00 pm-10:51 pm
2 stops10h 51m
$307
PortlandChicago
PDX - ORD
PDXORD
Portland
Wed 8/5
10:59 pm-5:00 am
Nonstop4h 01m
Chicago O'Hare Intl
Tue 8/18
8:20 pm-8:11 am
1 stop13h 51m
$325
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 8/11
4:05 pm-11:59 pm
1 stop5h 54m
Chicago O'Hare Intl
Tue 8/18
7:00 am-9:29 am
Nonstop4h 29m
$325
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 7/18
10:40 pm-4:45 am
Nonstop4h 05m
Chicago O'Hare Intl
Mon 7/20
7:00 am-9:34 am
Nonstop4h 34m
$326
EugeneChicago
EUG - ORD
EUGORD
Eugene
Sun 9/20
12:31 pm-11:47 pm
1 stop9h 16m
Chicago O'Hare Intl
Thu 10/1
2:05 pm-11:54 pm
2 stops11h 49m
$328
EugeneChicago
EUG - ORD
EUGORD
Eugene
Thu 10/8
2:15 pm-8:26 pm
Nonstop4h 11m
Chicago O'Hare Intl
Mon 10/12
9:05 am-11:50 am
Nonstop4h 45m
$329
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 9/1
5:50 am-4:35 pm
2 stops8h 45m
Chicago Midway
Tue 9/8
8:55 pm-11:10 pm
Nonstop4h 15m
$331
BoiseChicago
BOI - ORD
BOIORD
Boise Air Term. Gowen Fld
Tue 7/21
7:57 am-6:57 pm
1 stop10h 00m
Chicago O'Hare Intl
Tue 7/21
8:20 pm-9:40 am
1 stop14h 20m
$335
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/2
1:25 pm-10:50 pm
1 stop7h 25m
Chicago Midway
Sun 9/6
8:35 pm-10:50 pm
Nonstop4h 15m
$336
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 9/25
2:27 pm-8:40 pm
Nonstop4h 13m
Chicago O'Hare Intl
Sat 10/3
8:40 am-2:26 pm
1 stop7h 46m
$336
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Oregon to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon with our price prediction graph.
EUG-MDW
PDX-ORD
PDX-MDW
EUG-ORD
BOI-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Oregon to Chicago
USOR-CHI
EUG-MDW
PDX-ORD
PDX-MDW
EUG-ORD
What is the cheapest month to book a flight from Oregon to Chicago?
Currently, April is the cheapest month in which you can book a flight from Oregon to Chicago (average of $108). Flying from Oregon to Chicago in November is currently the most expensive (average of $1,467). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from OR to CHI?
Find hourly flight availability from Oregon to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 16, 2026.
When flying from Oregon to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 35% versus a flight at noon.
Weekly flight availability from Oregon to Chicago
Explore weekly flight availability from Oregon to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 16, 2026.
The most flights from USOR to CHI are scheduled on a Monday (40 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).
How much does it cost to fly round-trip from Oregon to Chicago?
How far ahead should I book a flight from Oregon to Chicago?
To ensure you get the cheapest price possible for a flight from Oregon to Chicago, you should look to book at least 42 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Oregon to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Oregon to Chicago. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Oregon to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Oregon to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Oregon to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 16, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oregon to Chicago by cabin class
Find flights from Oregon to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oregon and Chicago flights
Browse other Oregon and Chicago flight options. Last updated on June 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oregon to Chicago flights
Consider these flights traveling from Oregon to Chicago.
Top 7 airlines flying from Oregon to Chicago
Discover the top 7 airlines that operate flights from Oregon to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$93 | Average$247 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$96 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$108 | Average$354 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$172 | Average$327 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$386 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$198 | Average$410 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$218 | Average$407 | FlexibilityNo cancel fee | On-time69% |