Cheap flights from Portland to Chicago

One-way fares from $175 · PDX → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Portland
Cheapest fare
$175

American Airlines · Fri, Dec 18

Cheapest month
December

from $175

Direct flights
Yes

American Airlines

Flight time
3h 54m

2,820 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 $181
  2. December 2026 Cheapest $175

Cheapest dates in December 2026

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

American Airlines
Depart23:31 Fri, Dec 18PDX → ORD 3h 54m · Direct
$175one way, per person
View deal
See every date in December 2026 →

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About flights from Portland to Chicago

Portland (PDX) and Chicago (CHI) are about 2,820 km apart. Direct flights take around 3h 54m, and recent direct fares were with American Airlines. Over the next few months, one-way fares start from $175, and December 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 $175 with American Airlines, departing Friday, December 18, 2026. Over the coming months, the lowest fare in each month ranges from $175 to $181.

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

December 2026 currently has the lowest fares, from $175 one way.

Are there direct flights from Portland to Chicago?

Yes. Recent direct fares were with American Airlines.

How long is the flight from Portland to Chicago?

A direct flight takes about 3h 54m. Portland and Chicago are around 2,820 km apart.

Which airlines fly from Portland to Chicago?

Recent fares on this route were with Frontier Airlines and American Airlines.

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