Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.
Prepay checked bags 24 hours before to save on fees.

Most accurate provider | Justfly.com 3 stars |
|---|---|
Most trusted provider | Justfly.com 3 stars |
Round-trip from | $236 (Alaska Airlines) |
One-way from | $109 (Alaska Airlines) |
Popular in | March |
Cheapest in | August |
Average price | $432 |
Good round-trip deal | $348 or less |
Good one-way deal | $179 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
jue. 1/1
11:00 pm-5:02 am
Nonstop4h 02m
Chicago O'Hare Intl
lun. 1/5
8:58 pm-9:44 am
1 stop14h 46m
PortlandChicago
PDX - ORD
PDXORD
Portland
mié. 1/7
5:00 am-1:24 pm
1 stop6h 24m
Chicago O'Hare Intl
mié. 1/14
2:36 pm-9:12 pm
1 stop8h 36m
PortlandChicago
PDX - ORD
PDXORD
Portland
vie. 2/20
7:00 am-1:11 pm
Nonstop4h 11m
Chicago O'Hare Intl
mar. 3/3
3:54 pm-10:41 pm
1 stop8h 47m
PortlandChicago
PDX - ORD
PDXORD
Portland
jue. 1/8
11:59 pm-6:00 am
Nonstop4h 01m
Chicago O'Hare Intl
lun. 1/12
9:10 am-11:57 am
Nonstop4h 47m
PortlandChicago
PDX - ORD
PDXORD
Portland
dom. 1/25
7:10 am-5:10 pm
1 stop8h 00m
Chicago O'Hare Intl
mar. 1/27
2:06 pm-4:48 pm
Nonstop4h 42m
PortlandChicago
PDX - ORD
PDXORD
Portland
sáb. 1/24
1:24 pm-9:15 pm
1 stop5h 51m
Chicago O'Hare Intl
lun. 1/26
1:55 pm-9:12 pm
1 stop9h 17m
PortlandChicago
PDX - ORD
PDXORD
Portland
vie. 1/23
1:24 pm-9:15 pm
1 stop5h 51m
Chicago O'Hare Intl
dom. 1/25
4:15 pm-6:56 pm
Nonstop4h 41m
PortlandChicago
PDX - ORD
PDXORD
Portland
jue. 1/8
7:05 am-1:10 pm
Nonstop4h 05m
Chicago O'Hare Intl
jue. 1/15
3:35 pm-8:47 pm
1 stop7h 12m
PortlandChicago
PDX - ORD
PDXORD
Portland
vie. 1/16
3:45 pm-11:59 pm
1 stop6h 14m
Chicago O'Hare Intl
dom. 1/18
8:55 am-2:48 pm
1 stop7h 53m
PortlandChicago
PDX - ORD
PDXORD
Portland
vie. 1/23
2:38 pm-11:50 pm
1 stop7h 12m
Chicago O'Hare Intl
dom. 1/25
2:06 pm-4:48 pm
Nonstop4h 42m
| 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*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 88 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $120). Flying from Portland to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $241). 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 Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 37% versus a flight in the morning.
Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport flight should consider departing on Wednesday afternoons 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.
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Art,Dec 2025
SAN - OGG
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Art,Dec 2025
SAN - OGG
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Art,Dec 2025
SAN - OGG
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Art,Dec 2025
SAN - OGG
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Art,Dec 2025
SAN - OGG
Food
Boarding
Comfort
Overall
Entertainment
Crew
Reviews
Art,Dec 2025
SAN - OGG
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$243 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$184 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$123 | Average$288 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$284 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$194 | Average$322 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$217 | Average$346 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$221 | Average$379 | FlexibilityNo cancel fee | On-time69% |