Alaska's Premium Class offers extra legroom and free cocktails, ideal for medium-haul flights.
Alaska's Wi-Fi is a flat fee, perfect for getting work done on longer flights.

Most accurate provider | Justfly.com 3 stars |
|---|---|
Most trusted provider | Justfly.com 3 stars |
Round-trip from | $210 (Kiwi.com) |
One-way from | $113 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $317 |
Good round-trip deal | $263 or less |
Good one-way deal | $191 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 2/18
2:05 pm-4:39 pm
Nonstop4h 34m
Portland
Tue 2/24
7:00 am-1:04 pm
Nonstop4h 04m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 12/16
9:05 am-11:48 am
Nonstop4h 43m
Portland
Tue 12/23
7:45 pm-5:27 am
1 stop7h 42m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 1/9
8:00 am-1:48 pm
1 stop7h 48m
Portland
Tue 1/13
7:05 am-1:10 pm
Nonstop4h 05m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 12/19
7:00 am-9:50 am
Nonstop4h 50m
Portland
Sat 1/3
11:00 pm-5:02 am
Nonstop4h 02m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Thu 12/4
2:05 pm-4:48 pm
Nonstop4h 43m
Portland
Sun 12/7
5:49 pm-6:21 am
1 stop10h 32m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 3/10
6:50 pm-12:03 am
1 stop7h 13m
Portland
Wed 3/11
7:00 am-1:04 pm
Nonstop4h 04m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 2/18
2:20 pm-7:11 pm
1 stop6h 51m
Portland
Mon 2/23
12:55 am-8:47 am
1 stop5h 52m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 12/24
2:06 pm-4:44 pm
Nonstop4h 38m
Portland
Tue 12/30
9:34 pm-2:37 pm
1 stop15h 03m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 3/13
6:50 pm-12:03 am
1 stop7h 13m
Portland
Tue 3/17
10:30 am-11:10 pm
1 stop10h 40m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Thu 11/20
7:32 pm-5:18 pm
1 stop23h 46m
Portland
Sun 11/23
6:36 pm-10:39 am
1 stop14h 03m
| 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*2 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Booking 12 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Portland. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland (average of $143). Flying from Chicago O'Hare Intl Airport to Portland in March is currently the most expensive (average of $238). 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.
When flying from Chicago O'Hare Intl Airport to Portland, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 33% versus a flight at noon.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland flight should consider departing on Wednesday 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.
Boarding
Entertainment
Overall
Food
Comfort
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Entertainment
Overall
Food
Comfort
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Entertainment
Overall
Food
Comfort
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Entertainment
Overall
Food
Comfort
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Entertainment
Overall
Food
Comfort
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Entertainment
Overall
Food
Comfort
Crew
Reviews
Anonymous,Sep 2025
BOS - HNL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$184 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$88 | Average$372 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$134 | Average$284 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$198 | Average$298 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$213 | Average$318 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$226 | Average$370 | FlexibilityNo cancel fee | On-time69% |