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 | $208 (Frontier) |
One-way from | $116 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $314 |
Good round-trip deal | $263 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 12/17
8:55 am-4:43 pm
1 stop9h 48m
Portland
Tue 12/30
11:00 pm-5:02 am
Nonstop4h 02m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Mon 2/16
7:45 am-12:36 pm
1 stop6h 51m
Portland
Thu 2/19
1:45 pm-11:59 pm
1 stop8h 14m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
Tue 3/10
2:00 pm-8:30 pm
1 stop8h 30m
Portland
Tue 3/10
12:55 am-8:54 am
1 stop5h 59m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 12/10
1:13 pm-7:35 pm
1 stop8h 22m
Portland
Mon 12/15
12:32 am-8:40 am
1 stop6h 08m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Mon 12/15
2:05 pm-4:48 pm
Nonstop4h 43m
Portland
Sat 1/17
7:10 am-11:55 pm
1 stop14h 45m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 12/3
2:05 pm-4:48 pm
Nonstop4h 43m
Portland
Fri 12/5
1:34 pm-11:59 pm
1 stop8h 25m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 12/5
8:50 am-12:54 pm
1 stop6h 04m
Portland
Fri 12/5
12:32 am-10:33 am
1 stop8h 01m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Wed 12/3
7:50 am-3:33 pm
1 stop9h 43m
Portland
Thu 12/4
12:32 am-8:40 am
1 stop6h 08m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Tue 12/9
2:05 pm-4:48 pm
Nonstop4h 43m
Portland
Sat 12/13
7:04 am-1:09 pm
Nonstop4h 05m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
Fri 11/28
7:00 am-9:39 am
Nonstop4h 39m
Portland
Fri 12/5
1:34 pm-11:59 pm
1 stop8h 25m
| 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 Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 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, November is the cheapest month in which you can book a flight from Chicago to Portland (average of $143). Flying from Chicago to Portland in May is currently the most expensive (average of $199). 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 22% 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Boarding
Crew
Overall
Food
Comfort
Entertainment
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Crew
Overall
Food
Comfort
Entertainment
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Crew
Overall
Food
Comfort
Entertainment
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Crew
Overall
Food
Comfort
Entertainment
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Crew
Overall
Food
Comfort
Entertainment
Reviews
Anonymous,Sep 2025
BOS - HNL
Boarding
Crew
Overall
Food
Comfort
Entertainment
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$110 | Average$220 | 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% | |
| Cheapest$238 | Average$432 | FlexibilityNo cancel fee | On-time63% |