Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago Portland-Oregon | Outbound 11/09/25 direct AS0413 04h 39min | Return 12/07/25 1 Stopover (SAN) AS1312, AS1493 07h 19min | | ![]() | ? | $215 | |
Best option Chicago Portland-Oregon | Outbound 02/13/26 direct AS0325 04h 34min | Return 02/26/26 direct AS0324 04h 04min | | ![]() | ? | $239 | |
Chicago Portland-Oregon | Outbound 11/09/25 direct AS0413 04h 39min | Return 12/07/25 1 Stopover (SEA) AS3365, AS0570 07h 29min | | ![]() | ? | $233 | |
Chicago Portland-Oregon | Outbound 11/09/25 1 Stopover (DEN) F91483, F92553 07h 56min | Return 12/07/25 1 Stopover (SAN) AS1312, AS1493 07h 19min | | ![]() | $234 | ||
Chicago Portland-Oregon | Outbound 11/09/25 direct AS0413 04h 39min | Return 12/07/25 1 Stopover (SAN) AS0577, AS1478 09h 37min | | ![]() | $249 | ||
Chicago Portland-Oregon | Outbound 02/13/26 direct HA6293 04h 34min | Return 02/26/26 direct HA6373 04h 04min | | ![]() | $260 | ||
Chicago Portland-Oregon | Outbound 02/13/26 direct AS0325 04h 34min | Return 02/26/26 direct AS0324 04h 04min | | ![]() | ? | $263 | |
Chicago Portland-Oregon | Outbound 02/13/26 direct AS0325 04h 34min | Return 02/26/26 direct AS0324 04h 04min | | ![]() | ? | $280 | |
Chicago Portland-Oregon | Outbound 11/09/25 1 Stopover (SFO) UA2628, UA1668 10h 31min | Return 12/07/25 direct UA2635 04h 02min | | ![]() | ? | $289 | |
Chicago Portland-Oregon | Outbound 02/13/26 direct AS0325 04h 34min | Return 02/26/26 direct HA6373 04h 04min | | ![]() | ? | $364 |
Stops
- Direct flight
Airline
- Alaska Airlines
- Hawaiian Airlines
- United Airlines
- American Airlines
- Frontier 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 | $ 214,30 |
---|---|
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 $ 78
- Flight Chicago - Las Vegas from $ 110
- Flight Chicago - Los Angeles from $ 172
- Flight Chicago - Miami from $ 98
- Flight Chicago - San Francisco from $ 157
- Flight Chicago - Tampa from $ 69
- Flight Chicago - Denver from $ 101
- Flight Chicago - Orlando from $ 130
- Flight Chicago - New Orleans from $ 103
- Flight Chicago - Boston from $ 143
Alternative flights to Portland-Oregon
- Flight Atlanta - Portland-Oregon from $ 153
- Flight Denver - Portland-Oregon from $ 108
- Flight Dallas - Portland-Oregon from $ 202
- Flight Washington-DC - Portland-Oregon from $ 201
- Flight Boston - Portland-Oregon from $ 323
- Flight Washington DC - Portland-Oregon from $ 343
- Flight Chicago O'Hare - Portland-Oregon from $ 215
- Flight Baltimore - Portland-Oregon from $ 313
- Flight Cleveland - Portland-Oregon from $ 274
- Flight Washington DC - Portland-Oregon from $ 201
Flight destinations with a similar price
- Flight Portland-Oregon - Frankfurt from $ 671
Flight destinations with a similar price
- Flight Chicago - Washington-DC from $ 197
- Flight Chicago - Jacksonville, Florida from $ 204
- Flight Chicago - San Juan (Puerto Rico) from $ 234