
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $217 (Southwest) |
One-way from | $71 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $294 |
Good round-trip deal | $368 or less |
Good one-way deal | $118 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 1/6
3:35 pm-6:00 pm
Nonstop4h 25m
Portland
Tue 1/13
2:25 pm-10:40 pm
1 stop6h 15m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Thu 11/27
8:35 am-11:05 am
Nonstop4h 30m
Portland
Tue 12/2
7:15 am-5:05 pm
1 stop7h 50m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 12/10
1:50 pm-8:52 pm
1 stop9h 02m
Portland
Mon 12/15
12:32 am-9:19 am
1 stop6h 47m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 12/6
9:40 am-12:15 pm
Nonstop4h 35m
Portland
Tue 12/9
6:15 am-12:10 pm
Nonstop3h 55m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Wed 12/3
3:10 pm-10:00 pm
1 stop8h 50m
Portland
Sat 12/6
12:35 pm-10:45 pm
1 stop8h 10m
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Wed 12/10
7:02 pm-12:09 am
1 stop6h 07m
Boise Air Term. Gowen Fld
Sun 12/14
5:35 am-1:10 pm
1 stop6h 35m
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Fri 12/12
7:02 pm-12:09 am
1 stop6h 07m
Boise Air Term. Gowen Fld
Mon 12/15
5:35 am-1:10 pm
1 stop6h 35m
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Sat 12/13
7:02 pm-12:09 am
1 stop6h 07m
Boise Air Term. Gowen Fld
Sun 12/14
5:35 am-1:10 pm
1 stop6h 35m
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Sat 12/13
7:02 pm-12:09 am
1 stop6h 07m
Boise Air Term. Gowen Fld
Mon 12/15
5:35 am-1:10 pm
1 stop6h 35m
ChicagoBoise
MDW - BOI
MDWBOI
Chicago Midway
Thu 12/11
10:05 am-4:50 pm
1 stop7h 45m
Boise Air Term. Gowen Fld
Mon 12/15
1:25 pm-10:55 pm
1 stop8h 30m
Currently, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Oregon (average of $145). Flying from Chicago Midway Airport to Oregon in June is currently the most expensive (average of $397). 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.
It’s typically best to fly out from Chicago Midway Airport to Oregon at noon. Doing so could potentially save you 37% on the flight price compared to flying in the morning, which is usually more expensive.
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$110 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$238 | Average$436 | FlexibilityNo cancel fee | On-time63% |