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 | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $241 (Mytrip) |
One-way from | $110 (Alaska Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $447 |
Good round-trip deal | $288 or less |
Good one-way deal | $155 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
lun. 4/21
10:26 pm-6:05 pm
2 stops21h 39m
Portland
mer. 4/23
2:32 pm-5:45 am
2 stops13h 13m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
sam. 4/19
4:15 pm-6:35 pm
Nonstop4h 20m
Portland
sam. 4/26
11:50 am-10:15 pm
1 stop8h 25m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
jeu. 4/24
8:20 pm-11:02 pm
Nonstop4h 42m
Portland
mar. 4/29
11:52 pm-5:57 am
Nonstop4h 05m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
jeu. 5/1
8:05 pm-11:19 am
1 stop17h 14m
Portland
dim. 5/4
11:02 am-12:31 am
2 stops35h 29m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
sam. 4/26
5:25 pm-10:25 pm
1 stop7h 00m
Portland
mar. 4/29
8:55 am-4:45 pm
1 stop5h 50m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
mer. 6/4
7:15 pm-11:43 pm
1 stop6h 28m
Portland
mer. 6/18
11:13 pm-7:50 am
1 stop6h 37m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
jeu. 4/17
3:16 pm-5:50 pm
Nonstop4h 34m
Portland
sam. 4/19
7:00 am-1:05 pm
Nonstop4h 05m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
sam. 4/19
5:59 pm-10:35 pm
1 stop6h 36m
Portland
sam. 4/26
10:59 pm-8:40 am
1 stop7h 41m
ChicagoPortland
ORD - PDX
ORDPDX
Chicago O'Hare Intl
jeu. 4/24
4:12 pm-6:45 pm
Nonstop4h 33m
Portland
lun. 4/28
11:59 pm-5:56 am
Nonstop3h 57m
ChicagoPortland
MDW - PDX
MDWPDX
Chicago Midway
ven. 4/11
8:36 pm-8:56 am
1 stop14h 20m
Portland
mar. 4/15
9:59 am-12:21 am
1 stop12h 22m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy- | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy- | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*2 stars | |
Price Accuracy1 star | Trust Score*3 stars |
To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 24 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 $277). Flying from Chicago to Portland in March is currently the most expensive (average of $370). 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 in the afternoon, when flights are generally more expensive, you can save up to 44% 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 Saturday 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.
In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.
If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Comfort
Crew
Food
Entertainment
Boarding
Overall
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$82 | Average$138 | FlexibilityNo cancel fee | On-time65% | |
Cheapest$108 | Average$190 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$173 | Average$303 | FlexibilityNo cancel fee | On-time85% | |
Cheapest$176 | Average$288 | FlexibilityNo cancel fee | On-time75% | |
Cheapest$176 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$196 | Average$334 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$218 | Average$390 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$237 | Average$432 | FlexibilityNo cancel fee | On-time63% |