| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Portland-Oregon | Outbound 07/26/26 direct AA2284 04h 25min | Return 08/05/26 direct AS0376 04h 04min |  American Airlines |  | ? | $238 | |
| Chicago Portland-Oregon | Outbound 07/26/26 1 Stopover (MSP) SY0262, SY0295 24h 05min | Return 08/05/26 1 Stopover (MSP) SY0296, SY0261 23h 14min |  Sun Country Airlines |  | $448 | ||
| Chicago Portland-Oregon | Outbound 07/26/26 direct AS0413 04h 28min | Return 08/05/26 direct AS0376 04h 04min |  Alaska Airlines |  | ? | $264 | |
| Chicago Portland-Oregon | Outbound 05/16/26 direct AA1229 04h 31min | Return 05/29/26 1 Stopover (SAN) AS0586, AS1478 09h 46min | American Airlines | | ? | $275 | |
| Chicago Portland-Oregon | Outbound 07/26/26 direct AS0413 04h 28min | Return 08/05/26 direct AS0376 04h 04min | Alaska Airlines |  | $282 | ||
| Chicago Portland-Oregon | Outbound 07/26/26 direct AS0413 04h 28min | Return 08/05/26 direct AS0376 04h 04min | Alaska Airlines |  | ? | $302 | |
| Chicago Portland-Oregon | Outbound 08/03/26 direct AA1317 04h 27min | Return 08/28/26 direct AS0376 04h 06min | American Airlines | | ? | $316 | |
| 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 05/16/26 1 Stopover (SAN) AS1470, AS1402 09h 53min | Return 05/29/26 1 Stopover (SEA) AS3038, AS0410 08h 45min | 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 |
Stops
- Direct flight
Airline
- Alaska Airlines
- American Airlines
- Sun Country Airlines
- Frontier Airlines
- United Airlines
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 | $237.29 |
|---|---|
| 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
- Flight Chicago - New York from $149
- Flight Chicago - Las Vegas from $127
- Flight Chicago - Los Angeles from $169
- Flight Chicago - Miami from $135
- Flight Chicago - San Francisco from $161
- Flight Chicago - Tampa from $165
- Flight Chicago - Denver from $145
- Flight Chicago - Orlando from $119
- Flight Chicago - New Orleans from $160
- Flight Chicago - Boston from $193
Alternative flights to Portland-Oregon
- Flight Atlanta - Portland-Oregon from $201
- Flight Denver - Portland-Oregon from $124
- Flight Dallas - Portland-Oregon from $268
- Flight Washington-DC - Portland-Oregon from $343
- Flight Boston - Portland-Oregon from $271
- Flight Washington DC - Portland-Oregon from $398
- Flight Chicago O'Hare - Portland-Oregon from $238
- Flight Baltimore - Portland-Oregon from $298
- Flight Cleveland - Portland-Oregon from $434
- Flight Washington DC - Portland-Oregon from $343
Flight destinations with a similar price
- Flight Portland-Oregon - Frankfurt from $701
- Flight Portland-Oregon - Munich from $680
Flight destinations with a similar price
- Flight Chicago - Washington-DC from $239
- Flight Chicago - Fort Myers from $236
- Flight Chicago - Charlotte from $226
- Flight Chicago - Philadelphia from $250
- Flight Chicago - Amsterdam from $224
- Flight Chicago - Jacksonville, Florida from $224
- Flight Chicago - Guadalajara from $260
- Flight Chicago - San Juan (Puerto Rico) from $254