Alaska's Premium Class offers extra legroom and free cocktails, ideal for a comfortable flight.
Alaska Airlines' Wi-Fi is a bargain, perfect for getting work done on longer flights.

Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $223 (Kiwi.com) |
One-way from | $119 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $417 |
Good round-trip deal | $280 or less |
Good one-way deal | $118 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 1/14
9:10 am-11:57 am
Nonstop4h 47m
Portland
Sun 1/18
8:30 am-6:46 pm
1 stop8h 16m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 1/20
2:06 pm-4:48 pm
Nonstop4h 42m
Portland
Wed 1/28
1:38 pm-11:50 pm
1 stop8h 12m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 3/13
2:07 pm-4:50 pm
Nonstop4h 43m
Portland
Tue 3/17
7:00 am-1:11 pm
Nonstop4h 11m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 1/6
4:15 pm-6:56 pm
Nonstop4h 41m
Portland
Thu 1/15
7:00 am-1:05 pm
Nonstop4h 05m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 2/17
2:07 pm-4:50 pm
Nonstop4h 43m
Portland
Sat 2/21
8:30 am-4:33 pm
1 stop6h 03m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 1/6
9:10 am-11:57 am
Nonstop4h 47m
Portland
Thu 1/8
1:24 pm-9:15 pm
1 stop5h 51m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Sat 1/10
12:40 pm-7:55 pm
1 stop9h 15m
Portland
Sat 1/17
12:45 pm-8:30 pm
1 stop5h 45m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 1/21
8:00 am-1:48 pm
1 stop7h 48m
Portland
Tue 1/27
9:10 am-5:10 pm
1 stop6h 00m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 1/7
8:00 am-12:38 pm
1 stop6h 38m
Portland
Wed 1/14
7:18 am-11:37 pm
1 stop14h 19m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 1/13
1:49 pm-8:12 pm
1 stop8h 23m
Portland
Tue 1/20
11:59 am-10:22 pm
1 stop8h 23m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 60 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.
Currently, January is the cheapest month in which you can book a flight from Chicago to Portland (average of $123). Flying from Chicago to Portland 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.
Unlike at noon, when flights are generally more expensive, you can save up to 26% on flights from Chicago to Portland by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Thursday evenings 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.
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
Art,Dec 2025
SAN - OGG
Entertainment
Crew
Overall
Food
Boarding
Comfort
Reviews
Art,Dec 2025
SAN - OGG
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$182 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$134 | Average$284 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$138 | Average$220 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$200 | Average$309 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$211 | Average$355 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$213 | Average$321 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$238 | Average$432 | FlexibilityNo cancel fee | On-time63% |