
Keep the following information in mind while searching for Illinois to Oregon flight deals. Data was last updated November 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $257 (Alaska Airlines) |
One-way from | $177 (Alaska Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $436 |
Good round-trip deal | $357 or less |
Good one-way deal | $224 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 11/25
9:25 pm-12:10 am
Nonstop4h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoEugene
ORD Chicago O'Hare Intl - EUG Eugene
ORDEUG
Chicago O'Hare Intl
Wed 12/23
7:35 am-12:12 pm
1 stop30h 37m
Eugene
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Wed 11/25
7:45 pm-10:27 pm
Nonstop4h 42m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Mon 12/21
9:30 pm-12:15 am
Nonstop4h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Thu 12/24
8:40 pm-11:25 pm
Nonstop4h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Mon 11/23
5:15 am-12:36 pm
1 stop9h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Fri 12/18
6:20 am-10:39 am
1 stop6h 19m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Sat 11/21
3:47 pm-10:26 pm
2 stops8h 39m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
ORD Chicago O'Hare Intl - PDX Portland
ORDPDX
Chicago O'Hare Intl
Wed 11/25
2:44 pm-11:51 pm
2 stops11h 07m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoEugene
MDW Chicago Midway - EUG Eugene
MDWEUG
Chicago Midway
Fri 2/12
10:05 am-3:35 pm
1 stop7h 30m
Eugene
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
Everything you need to know about your flight from Illinois to Oregon
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
Sarah,Aug 2024
MDW - AUS
Overall
Boarding
Entertainment
Comfort
Food
Crew
Reviews
Sarah,Aug 2024
MDW - AUS
Find useful and relevant information for your journey from Illinois to Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$155 | Average$250 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$191 | Average$218 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$480 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$217 | Average$492 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$222 | Average$519 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$239 | Average$374 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$256 | Average$480 | FlexibilityNo cancel fee | On-timeN/A |