$54+ Cheap flights from Oregon to Illinois
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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Mar 3 — Mar 101
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oregon to Illinois 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Oregon to Illinois
Cheapest
Best
Last-minute
One-way
Cheapest flights from Oregon to IllinoisExplore the most affordable flight options available from Oregon to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 1, 2026.
Explore the most affordable flight options available from Oregon to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 1, 2026.
This Delta deal was found by Cheapflights users on 1/30. 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.
Tue 4/711:15 pm
PDX
- ORD
1 stop7h 55m
Delta
Sat 4/117:25 am
ORD
- PDX
1 stop7h 44m
Delta
Deal found 1/30![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:25 am
PDX
- MDW
1 stop7h 50m
Southwest
Tue 3/175:45 am
MDW
- PDX
1 stop10h 05m
Southwest
Deal found 1/30![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:14 pm
PDX
- ORD
1 stop10h 25m
Frontier
Thu 4/2310:55 am
ORD
- PDX
1 stop26h 08m
Frontier
Deal found 1/30![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
- ORD
1 stop20h 02m
Frontier
Mon 4/2710:55 am
ORD
- PDX
1 stop28h 07m
Frontier
Deal found 1/30![Frontier logo]()
$222
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:10 am
PDX
- MDW
1 stop10h 30m
Southwest
Sat 2/288:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Deal found 1/30![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 2/183:50 pm
PDX
- ORD
1 stop6h 09m
United Airlines
Wed 3/188:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 1/31![United Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:55 pm
PDX
- MDW
1 stop7h 05m
Southwest
Sat 5/21:55 pm
MDW
- PDX
1 stop6h 50m
Southwest
Deal found 1/30![Southwest logo]()
$224
This Expedia deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/139:26 pm
PDX
- ORD
1 stop15h 32m
Alaska Airlines
Tue 3/172:07 pm
ORD
- PDX
Nonstop4h 43m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:52 pm
PDX
- ORD
1 stop15h 16m
Multiple Airlines
Wed 3/188:58 pm
ORD
- PDX
2 stops40h 11m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 1/30. 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 2/2112:09 pm
PDX
- ORD
1 stop9h 47m
Delta
Mon 2/233:59 pm
ORD
- PDX
1 stop6h 31m
Delta
Deal found 1/30![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 1/30. 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.
Fri 2/2012:40 am
PDX
- MDW
1 stop8h 23m
Delta
Mon 2/231:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 1/30![Delta logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 3/35:40 am
BOI
- ORD
1 stop6h 31m
Alaska Airlines
Tue 3/173:54 pm
ORD
- BOI
1 stop9h 05m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$229
Best flights from Oregon to IllinoisDiscover carefully curated flight deals from Oregon to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 1, 2026.
Discover carefully curated flight deals from Oregon to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 1, 2026.
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/311:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Tue 3/102:01 pm
ORD
- PDX
1 stop9h 09m
United Airlines
Deal found 1/31![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/141:49 pm
PDX
- ORD
1 stop8h 02m
Delta
Wed 3/181:57 pm
ORD
- PDX
1 stop9h 56m
Delta
Deal found 1/31![Delta logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 3/107:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Fri 3/133:54 pm
ORD
- PDX
1 stop8h 47m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/65:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Mon 3/910:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 1/31![Southwest logo]()
$217
This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:52 pm
PDX
- MLI
1 stop7h 36m
American Airlines
Sat 2/287:09 pm
MLI
- PDX
1 stop7h 08m
American Airlines
Deal found 1/30![American Airlines logo]()
$251
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 5/61:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Fri 5/88:12 pm
STL
- PDX
1 stop17h 30m
Frontier
Deal found 1/31![Frontier logo]()
$256
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/611:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Mon 3/94:40 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 1/31![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/212:40 am
PDX
- ORD
1 stop6h 00m
Delta
Tue 3/102:20 pm
ORD
- PDX
1 stop8h 38m
Delta
Deal found 1/31![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/212:35 pm
PDX
- MDW
1 stop6h 45m
Southwest
Thu 4/239:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 1/31![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 3/35:40 am
BOI
- ORD
1 stop6h 31m
Alaska Airlines
Tue 3/173:54 pm
ORD
- BOI
1 stop9h 05m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Sat 3/711:28 pm
PDX
- ORD
Nonstop3h 52m
United Airlines
Thu 3/122:01 pm
ORD
- PDX
1 stop9h 09m
United Airlines
Deal found 1/30![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/125:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Mon 3/1610:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 1/31![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/1411:15 pm
PDX
- MDW
1 stop7h 32m
Delta
Sat 4/182:12 pm
MDW
- PDX
1 stop7h 53m
Delta
Deal found 1/31![Delta logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/282:57 pm
BOI
- ORD
1 stop8h 02m
Alaska Airlines
Tue 5/56:00 am
ORD
- BOI
1 stop7h 35m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 1/29. 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.
Thu 3/511:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Mon 3/98:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 1/29![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/29. 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.
Thu 3/511:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Mon 3/910:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 1/29![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/111:55 pm
PDX
- ORD
1 stop7h 56m
Delta
Mon 3/167:10 pm
ORD
- PDX
1 stop6h 44m
Delta
Deal found 1/31![Delta logo]()
$227
This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/55:10 am
EUG
- STL
1 stop6h 37m
American Airlines
Wed 4/88:00 am
STL
- EUG
1 stop7h 26m
American Airlines
Deal found 1/30![American Airlines logo]()
$282
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 3/105:42 am
EUG
- ORD
1 stop6h 31m
Alaska Airlines
Wed 3/113:54 pm
ORD
- EUG
1 stop7h 37m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/2211:59 pm
PDX
- ORD
Nonstop4h 04m
United Airlines
Tue 4/287:40 am
ORD
- PDX
1 stop8h 50m
United Airlines
Deal found 1/31![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/95:10 am
PDX
- MDW
Nonstop3h 55m
Southwest
Mon 4/139:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 1/31![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/1311:15 pm
PDX
- ORD
1 stop7h 55m
Delta
Tue 3/177:20 am
ORD
- PDX
1 stop7h 15m
Delta
Deal found 1/31![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/111:59 pm
PDX
- ORD
Nonstop3h 54m
United Airlines
Sun 3/88:04 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 1/31![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/29. 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 3/1311:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Sun 3/159:40 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 1/29![Southwest logo]()
$217
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 5/14:02 pm
EUG
- ORD
1 stop20h 06m
Alaska Airlines
Mon 5/48:48 pm
ORD
- EUG
1 stop17h 58m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 1/30. 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 2/215:15 am
EUG
- STL
1 stop6h 17m
Delta
Tue 2/247:00 am
STL
- EUG
1 stop6h 50m
Delta
Deal found 1/30![Delta logo]()
$237
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2111:18 am
PDX
- STL
Nonstop3h 48m
Alaska Airlines
Wed 5/276:20 pm
STL
- PDX
Nonstop4h 17m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/127:49 pm
PDX
- ORD
1 stop7h 18m
United Airlines
Mon 3/164:40 pm
ORD
- PDX
Nonstop4h 34m
United Airlines
Deal found 1/31![United Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 1/29. 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.
Wed 4/2911:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 5/39:45 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 1/29![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 1/30. 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 2/285:15 am
EUG
- STL
1 stop6h 17m
Delta
Sat 3/77:00 am
STL
- EUG
1 stop6h 50m
Delta
Deal found 1/30![Delta logo]()
$237
Last-minute flights from Oregon to IllinoisDiscover last-minute flight deals from Oregon to Illinois. Data last updated February 1, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Illinois. Data last updated February 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:35 pm
PDX
- ORD
Nonstop3h 57m
American Airlines
Tue 2/179:46 pm
ORD
- PDX
Nonstop4h 31m
American Airlines
Deal found 1/30![American Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 1/30. 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.
Tue 2/179:45 pm
PDX
- ORD
1 stop8h 56m
Delta
Tue 2/247:15 am
ORD
- PDX
1 stop7h 10m
Delta
Deal found 1/30![Delta logo]()
$234
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Wed 2/187:00 am
PDX
- ORD
Nonstop4h 04m
United Airlines
Fri 2/207:59 pm
ORD
- PDX
Nonstop4h 41m
United Airlines
Deal found 1/30![United Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:25 am
PDX
- MDW
1 stop7h 50m
Southwest
Fri 2/2012:05 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 1/30![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 2/187:25 am
PDX
- MDW
1 stop7h 50m
Southwest
Sat 2/218:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Deal found 1/31![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 1/30. 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.
Fri 2/2012:40 am
PDX
- MDW
1 stop8h 23m
Delta
Mon 2/231:49 pm
MDW
- PDX
1 stop8h 41m
Delta
Deal found 1/30![Delta logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 2/217:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Wed 3/186:00 am
ORD
- PDX
1 stop6h 33m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 1/30. 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 2/2112:09 pm
PDX
- ORD
1 stop9h 47m
Delta
Mon 2/233:59 pm
ORD
- PDX
1 stop6h 31m
Delta
Deal found 1/30![Delta logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 2/217:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Fri 3/202:09 pm
ORD
- PDX
Nonstop4h 41m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$232
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:25 am
PDX
- MDW
1 stop7h 50m
Southwest
Tue 3/175:45 am
MDW
- PDX
1 stop10h 05m
Southwest
Deal found 1/30![Southwest logo]()
$217
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Tue 2/243:47 pm
BOI
- ORD
1 stop7h 09m
Alaska Airlines
Wed 2/257:00 am
ORD
- BOI
1 stop8h 58m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:10 am
PDX
- MDW
1 stop10h 30m
Southwest
Sat 2/288:30 pm
MDW
- PDX
Nonstop4h 30m
Southwest
Deal found 1/30![Southwest logo]()
$223
One-way flights from Oregon to IllinoisSearch for one-way flight options from Oregon to Illinois. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
Search for one-way flight options from Oregon to Illinois. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
This Trip.com deal was found by Cheapflights users on 1/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/30![Frontier logo]()
$54
This Trip.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Thu 3/1212:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1312:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/30![Frontier logo]()
$79
This Frontier deal was found by Cheapflights users on 1/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:38 pm
BOI
- ORD
1 stop9h 36m
Frontier
Deal found 1/29![Frontier logo]()
$80
This Trip.com deal was found by Cheapflights users on 1/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:36 pm
BOI
- ORD
1 stop9h 38m
Frontier
Deal found 1/30![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Fri 2/2711:56 am
BOI
- ORD
2 stops34h 21m
Frontier
Deal found 1/29![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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.
Sun 3/812:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/1512:04 pm
PDX
- STL
1 stop19h 45m
Frontier
Deal found 1/31![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 3/238:28 pm
BOI
- ORD
1 stop9h 11m
Hawaiian Airlines
Deal found 1/31![Hawaiian Airlines logo]()
$102
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” 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 4/3011:53 am
BOI
- ORD
1 stop20h 57m
Frontier
Deal found 1/31![Frontier logo]()
$107
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:48 pm
PDX
- STL
1 stop27h 24m
Frontier
Deal found 1/30![Frontier logo]()
$107
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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 2/267:00 am
PDX
- ORD
Nonstop4h 11m
Alaska Airlines
Deal found 1/30![Alaska Airlines logo]()
$109
Find flight deals from Oregon to Illinois
Keep the following information in mind while searching for Oregon to Illinois flight deals. Data was last updated February 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Delta) |
One-way from | $54 (Trip.com) |
Popular in | March |
Cheapest in | August |
Average price | $326 |
Good round-trip deal | $318 or less |
Good one-way deal | $166 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Illinois 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 February 1, 2026.
Use the filters below to find and compare flights from Oregon to Illinois that are best for you.
Fly from
Oregon
Fly to
Illinois
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/3
11:59 pm-5:53 am
Nonstop3h 54m
Chicago O'Hare Intl
Tue 3/10
2:01 pm-9:10 pm
1 stop9h 09m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 3/14
1:49 pm-11:51 pm
1 stop8h 02m
Chicago O'Hare Intl
Wed 3/18
1:57 pm-9:53 pm
1 stop9h 56m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 3/10
7:00 am-1:11 pm
Nonstop4h 11m
Chicago O'Hare Intl
Fri 3/13
3:54 pm-10:41 pm
1 stop8h 47m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 3/6
5:20 am-11:15 am
Nonstop3h 55m
Chicago Midway
Mon 3/9
10:20 pm-12:45 am
Nonstop4h 25m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 3/6
11:59 pm-5:53 am
Nonstop3h 54m
Chicago O'Hare Intl
Mon 3/9
4:40 pm-7:14 pm
Nonstop4h 34m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Mon 3/2
12:40 am-8:40 am
1 stop6h 00m
Chicago O'Hare Intl
Tue 3/10
2:20 pm-8:58 pm
1 stop8h 38m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 4/21
2:35 pm-11:20 pm
1 stop6h 45m
Chicago Midway
Thu 4/23
9:50 pm-12:10 am
Nonstop4h 20m
$217
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 3/7
11:28 pm-5:20 am
Nonstop3h 52m
Chicago O'Hare Intl
Thu 3/12
2:01 pm-9:10 pm
1 stop9h 09m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 3/12
5:20 am-11:15 am
Nonstop3h 55m
Chicago Midway
Mon 3/16
10:20 pm-12:45 am
Nonstop4h 25m
$217
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 4/14
11:15 pm-8:47 am
1 stop7h 32m
Chicago Midway
Sat 4/18
2:12 pm-8:05 pm
1 stop7h 53m
$217
Showing 1-10 of 60 results
Best time to book a flight from Oregon to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Oregon with our price prediction graph.
PDX-ORD
PDX-MDW
RDM-ORD
BOI-ORD
EUG-STL
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 Illinois
USOR-USIL
PDX-ORD
PDX-MDW
RDM-ORD
BOI-ORD
What is the cheapest month to book a flight from Oregon to Illinois?
Currently, December is the cheapest month in which you can book a flight from Oregon to Illinois (average of $120). Flying from Oregon to Illinois in November is currently the most expensive (average of $236). 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 IL?
Find hourly flight availability from Oregon to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 1, 2026.
It’s optimal to fly from Oregon to Illinois in the afternoon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight in the evening.
What is the cheapest day to fly from Oregon to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Oregon to Illinois. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Oregon to Illinois flight should consider departing on Tuesday evenings 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 Oregon to Illinois
Explore weekly flight availability from Oregon to Illinois. 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 February 1, 2026.
The most flights from USOR to USIL are scheduled on a Friday (17 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (11 on average).
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated February 1, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oregon to Illinois to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Food
7.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Overall
8.0
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Jan 2026
STS - LAX
Related info for your journey
Find useful and relevant information for your journey from Oregon to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Oregon to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Top 8 airlines flying from Oregon to Illinois
Discover the top 8 airlines that operate flights from Oregon to Illinois. 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 February 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$361 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$194 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$125 | Average$323 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$179 | Average$421 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$184 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$474 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$215 | Average$400 | FlexibilityNo cancel fee | On-time75% |