Cheap flights from Portland to Chicago

One-way fares from $192 · PWM → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Portland
Cheapest fare
$192

American Airlines · Sat, Nov 21

Cheapest month
November

from $192

Direct flights
Not recently

Usually 1+ stop

Quickest trip
4h 19m

1,420 km

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Cheapest month to fly from Portland to Chicago

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $192

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

American Airlines
Depart05:26 Sat, Nov 21PWM → ORD 4h 31m · 1 stop
$192one way, per person
View deal
See every date in November 2026 →

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Getting around

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About flights from Portland to Chicago

Portland (PWM) and Chicago (CHI) are about 1,420 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 4h 19m. Over the next few months, one-way fares start from $192, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Portland to Chicago?

The cheapest one-way fare we've seen recently is $192 with American Airlines, departing Saturday, November 21, 2026.

What is the cheapest month to fly from Portland to Chicago?

November 2026 currently has the lowest fares, from $192 one way.

Are there direct flights from Portland to Chicago?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Portland to Chicago?

The quickest journey we've seen takes about 4h 19m. Portland and Chicago are around 1,420 km apart.

Which airlines fly from Portland to Chicago?

Recent fares on this route were with American Airlines.

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