Portland to Chicago (PDX-ORD): nonstop upgrade & award space

United Airlines, American Airlines, and Alaska Airlines fly nonstop between Portland (PDX) and Chicago (ORD), roughly 82 times a week. With this many departures on a short sector, premium cabins are small and turn over daily, so upgrade or award space opens and closes within hours. 2LNR tracks confirmed upgrade and award space on American Airlines and Alaska Airlines, on every PDX to ORD departure, so you know which flights have space before you book.

Schedule last confirmed . Departure times come from 2LNR's schedule data; confirm with the airline before you book.

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82
Nonstop flights a week
1,734 mi
Nonstop distance
Free
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Portland to Chicago flight schedule

Scheduled nonstop departures for PDX to ORD, last checked against our schedule feed on September 6, 2026. Airlines retime and cancel flights, so confirm with the airline before you book.

Schedule data dated .

Scheduled nonstop departures from Portland (PDX) to Chicago (ORD)
Date Flight Airline Departs PDX Arrives ORD Duration Aircraft
AA 3329American Airlines06:0112:154h 14m738
UA 2306United Airlines07:0213:154h 13m32Q
AS 324Alaska Airlines, Inc.07:0613:264h 20m73J
UA 2822United Airlines08:1714:304h 13m738
UA 1923United Airlines10:3516:484h 13m7M9
AA 2284American Airlines11:2617:424h 16m321
AA 1713American Airlines11:4818:124h 24m738
UA 2336United Airlines14:2720:404h 13m32Q
AS 376Alaska Airlines, Inc.22:5905:004h 1m73J
UA 2094United Airlines23:0205:034h 1m7M9
AA 1094American Airlines23:0805:084h321
AA 1818American Airlines23:0805:084h321
AA 3329American Airlines06:0112:154h 14m738
UA 2306United Airlines07:0213:154h 13m32Q
AS 324Alaska Airlines, Inc.07:0613:264h 20m73J
UA 2822United Airlines08:1514:284h 13m738
UA 1923United Airlines10:3516:484h 13m7M9
AA 2284American Airlines11:2617:424h 16m321
AA 1713American Airlines11:4818:124h 24m738
UA 2336United Airlines14:2720:404h 13m32Q
AS 376Alaska Airlines, Inc.22:5905:004h 1m73J
UA 2094United Airlines23:0205:034h 1m7M9
AA 1094American Airlines23:0805:084h321
AA 1818American Airlines23:0805:084h321
AA 3329American Airlines06:0112:154h 14m738
UA 2306United Airlines07:0213:154h 13m32Q
AS 324Alaska Airlines, Inc.07:0613:264h 20m73J
UA 2822United Airlines08:1514:284h 13m738
UA 1923United Airlines10:3516:484h 13m7M9
AA 2284American Airlines11:2617:424h 16m321
AA 1713American Airlines11:4818:124h 24m738
UA 2336United Airlines14:2720:404h 13m32Q
AS 376Alaska Airlines, Inc.22:5905:004h 1m73J
UA 2094United Airlines23:0205:034h 1m7M9
AA 1094American Airlines23:0805:084h321
AA 1818American Airlines23:0805:084h321
AA 3329American Airlines06:0112:154h 14m738
UA 2306United Airlines07:0213:154h 13m32Q
AS 324Alaska Airlines, Inc.07:0613:264h 20m7M9
UA 2822United Airlines08:1714:304h 13m738

Showing the first 40 of 80 scheduled PDX to ORD departures across the next 7 days with service. Every remaining date is on the interactive map.

Departure and arrival times are local at their own airport, so an arrival can fall on a different local date than the departure; the duration column is the true elapsed flying time. A dash means the airline has not filed that value in the schedule data we hold. Aircraft are IATA equipment codes as filed, and can change up to departure.

See every PDX to ORD date on the interactive map

Confirmed upgrade & award space on PDX to ORD departures

2LNR tracks confirmed upgrade and award space on American Airlines and Alaska Airlines, segment by segment and date by date. Open the calendar for Portland to Chicago to see which departures have space, the next 14 days free on every product and the full horizon on Pro.

See real availability

Confirmed upgrade and award seats on each PDX to ORD departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See PDX to ORD on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Portland to Chicago nonstop

Carriers operating PDX to ORD nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

See PDX to ORD on the interactive map →

Frequently asked questions about PDX to ORD

How far is Chicago from Portland?
PDX to ORD covers about 1,734 miles nonstop. Flight times vary by aircraft and season; the schedule table on this page lists each scheduled departure with its own times.
Which airlines fly nonstop from PDX to ORD?
United Airlines, American Airlines, and Alaska Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines and Alaska Airlines.
How many flights a week are there from PDX to ORD?
About 82 nonstop flights a week run between Portland and Chicago in the current schedule, operated by United Airlines, American Airlines, and Alaska Airlines. Frequency shifts by season, and the schedule table on this page shows what is scheduled next.
What time do flights from PDX to ORD depart?
Scheduled PDX to ORD nonstops in the next 7 days with service leave between 06:01 and 23:08, local time at Portland. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
How do I check upgrade or award availability on PDX to ORD?
Open the PDX to ORD route on the interactive map or the matrix to see confirmed upgrade and award space by date on American Airlines and Alaska Airlines, the next 14 days free and the full horizon on Pro. On Pro you can also set an alert on the route and 2LNR notifies you when space opens.

Never miss PDX to ORD upgrade or award space

See what is open by date on this route, the next 14 days free on every product and the full horizon on Pro.

Get started free