Flights from Chicago to Portland Oregon

Our cheapest offers for flights from Chicago to Portland Oregon

Here you can compare cheap flights from Chicago (CHI) to Portland Oregon (PDX) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Portland Oregon. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Best option
Chicago
Portland-Oregon
Outbound
04/03/26
direct
AS0325
04h 32min
Return
04/16/26
direct
AS0170
04h 07min
Alaska Airlines ?
$245
Chicago
Portland-Oregon
Outbound
04/03/26
direct
AS0325
04h 32min
Return
04/16/26
direct
AS0324
04h 07min
Alaska Airlines ?
$262
Chicago
Portland-Oregon
Outbound
04/03/26
direct
HA6293
04h 32min
Return
04/16/26
direct
HA6332
04h 07min
Hawaiian Airlines ?
$262
Chicago
Portland-Oregon
Outbound
04/03/26
direct
AS0325
04h 32min
Return
04/16/26
direct
AS0170
04h 07min
Alaska Airlines
$269
Chicago
Portland-Oregon
Outbound
04/03/26
direct
AS0325
04h 32min
Return
04/16/26
direct
AS0170
04h 07min
Alaska Airlines ?
$280
Chicago
Portland-Oregon
Outbound
04/05/26
1 Stopover (SEA)
AS0587, AS0466
07h 21min
Return
04/12/26
direct
AS0324
04h 07min
Alaska Airlines ?
$335
Chicago
Portland-Oregon
Outbound
04/03/26
direct
AS0325
04h 32min
Return
04/16/26
direct
AS0170
04h 07min
Alaska Airlines ?
$346
Chicago
Portland-Oregon
Outbound
04/05/26
1 Stopover (SEA)
AS0587, AS0466
07h 21min
Return
04/12/26
direct
AS0324
04h 07min
Alaska Airlines ?
$351
Chicago
Portland-Oregon
Outbound
04/05/26
1 Stopover (SEA)
AS0587, AS0466
07h 21min
Return
04/12/26
direct
AS0324
04h 07min
Alaska Airlines ?
$352
Chicago
Portland-Oregon
Outbound
04/05/26
1 Stopover (SEA)
AS0587, AS0466
07h 21min
Return
04/12/26
direct
AS0324
04h 07min
Alaska Airlines
$358
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Chicago to Portland Oregon

Favorite airline: Alaska Airlines
The favorite airline for flights from Chicago to Portland-Oregon is Alaska Airlines.
Alaska Airlines
48 %
United Airlines
15 %
Spirit Airlines
14 %
Direct flights are more expensive
Compared to direct flights, flights with a stopover on this route are on average 55 % cheaper.
non stop flight
1 stop
04h 37min
10h 55min
$245
$158
The favorite connection is non-stop
Direct flights are especially popular on this route. 63 % of travelers will book a direct flight.
Route
bookings
Direct flights
04h 37min, from $245
63 %
1 stopover Las Vegas - McCarran International Airport, NV
10h 55min, from $158
18 %
1 stopover Phoenix - Sky Harbor International Airport
10h 55min, from $171
8 %

Important flight information

Flight information: Chicago - Portland-Oregon

Roundtrip from $244.61
Flight duration min. 04:34 / max. 07:40
Return flight duration min. 03:45/ max. 06:15
Distance 2820 km
Flights per week 54
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Portland International Airport, Oregon (PDX)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Portland-Oregon
Flight destinations with a similar price
Flight destinations with a similar price