Portland International (PDX) to O'Hare International (ORD).
| Departure | Return | Price |
|---|---|---|
| 07/13/2026 | 07/22/2026 | $230 |
| 07/16/2026 | 07/22/2026 | $230 |
| 07/17/2026 | 07/22/2026 | $230 |
| 07/27/2026 | 08/05/2026 | $230 |
| 07/30/2026 | 08/05/2026 | $230 |
| 07/31/2026 | 08/05/2026 | $230 |
| 08/02/2026 | 08/10/2026 | $244 |
| 08/03/2026 | 08/10/2026 | $244 |
| 08/05/2026 | 08/10/2026 | $244 |
| 08/05/2026 | 08/13/2026 | $244 |
Based on current fares, August is the cheapest month to fly from Portland to Chicago, with average fares around $255 round trip (as low as $244).
See the full month-by-month and day-of-week price analysis
Best Time to Fly PDX → ORDDeparture date prices (economy, round trip). Green = cheap, red = expensive.
The cheapest month to fly from Portland to Chicago is August, with average round-trip fares around $255. Fares in August start as low as $244. The most expensive month is May, averaging $300.
A nonstop flight from Portland to Chicago takes approximately 4h.
The cheapest flight from Portland to Chicago currently starts at $230 round trip in economy class.
The average round-trip flight price from Portland to Chicago is $294 in economy class.
The distance is 1739 miles (2798 km). with a nonstop flight time of about 4h. The lowest fare currently available is $230 departing in July. The average round-trip fare is $294.
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