Portland (PDX) to Chicago (ORD) flights
3 airlines fly nonstop from Portland (PDX) to Chicago (ORD): Alaska Airlines, American Airlines and United Airlines. The two airports are 1,734 miles (2,791 km) apart. Alaska Airlines and American Airlines are in oneworld and United Airlines is in Star Alliance. There are also 49 ways to fly it with one stop, through Bozeman, Billings and Missoula and more.
Airlines flying nonstop from PDX to ORD
- Alaska Airlinesoneworld · bookable with 9 programsWho books it
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book PDX to ORD with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Alaska Atmos RewardsBooks Alaska Airlines, American Airlines
- American AAdvantageBooks Alaska Airlines, American Airlines
- British Airways ClubBooks Alaska Airlines, American Airlines
- Cathay Pacific Asia MilesBooks Alaska Airlines, American Airlines
- Finnair PlusBooks Alaska Airlines, American Airlines
- Iberia ClubBooks Alaska Airlines, American Airlines
- JAL Mileage BankBooks Alaska Airlines, American Airlines
- Qantas Frequent FlyerBooks Alaska Airlines, American Airlines
- Qatar Airways Privilege ClubBooks Alaska Airlines, American Airlines
- Air Canada AeroplanBooks United Airlines
- Air New Zealand AirpointsBooks United Airlines
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United Airlines
- Singapore Airlines KrisFlyerBooks United Airlines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
PDX to ORD with one stop
49 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Bozeman (BZN)Alaska Airlines, then American Airlines and United Airlines
- Via Billings (BIL)Alaska Airlines, then United Airlines and American Airlines
- Via Missoula (MSO)Alaska Airlines, then American Airlines and United Airlines
- Via Minneapolis (MSP)Delta Air Lines and Sun Country Airlines the whole way
+1 - Via Jackson (JAC)Alaska Airlines, then American Airlines and United Airlines
- Via Idaho Falls (IDA)Alaska Airlines, then American Airlines and United Airlines
- Via Spokane (GEG)Alaska Airlines, then United Airlines and American Airlines
- Via Boise (BOI)Alaska Airlines, then American Airlines and United Airlines
- Via Kalispell (FCA)Alaska Airlines, then United Airlines and American Airlines
- Via Seattle (SEA)Alaska Airlines and Delta Air Lines the whole way+1
- Via Hayden (HDN)Alaska Airlines, then American Airlines and United Airlines
- Via Denver (DEN)Frontier Airlines and United Airlines the whole way
+1
- Via Salt Lake City (SLC)Delta Air Lines the whole way
- Via Kansas City (MCI)Alaska Airlines and Southwest Airlines, then American Airlines and United Airlines
- Via Eugene (EUG)Alaska Airlines, then United Airlines
PDX to ORD: common questions
Which airlines fly nonstop from PDX to ORD?
Alaska Airlines (oneworld), American Airlines (oneworld) and United Airlines (Star Alliance) fly nonstop from Portland (PDX) to Chicago (ORD).
How far is Portland from Chicago by plane?
Portland (PDX) and Chicago (ORD) are 1,734 miles (2,791 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book PDX to ORD award flights?
22 programs can book at least one of the nonstop airlines: Alaska Atmos Rewards, American AAdvantage, British Airways Club, Cathay Pacific Asia Miles, Finnair Plus, Iberia Club, JAL Mileage Bank, Qantas Frequent Flyer and 14 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does PDX to ORD cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for PDX to ORD with taxes and fees.
Where can I connect between Portland and Chicago?
The most direct connections are through Bozeman (BZN), Billings (BIL), Missoula (MSO), Minneapolis (MSP) and Jackson (JAC). On 22 of them the same airline flies both flights, for example Delta Air Lines through Minneapolis.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.