Cheap flights from Chicago to Portland
Find cheap Portland to Chicago flights with our free search service. Compare all available fares for direct or connection flights from Portland to Chicago.
Chicago to Portland flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Chicago (CHI) - Portland (PDX) | 2026-10-16 | 2026-10-20 | 463 USD | 8 hours 15 minutes | Direct | 2026-09-26T21:27:21 |
| Chicago (CHI) - Portland (PDX) | 2026-10-16 | 2026-10-18 | 527 USD | 8 hours 15 minutes | Direct | 2026-09-26T19:32:39 |
Chicago to Portland flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| WN4389 | Chicago (MDW) | Portland (PDX) | 3:55 p.m. | 5:35 p.m. | B737 |
| WN4117 | Chicago (MDW) | Portland (PDX) | 11:35 a.m. | 1 p.m. | B737 |
| WN3357 | Chicago (MDW) | Portland (PDX) | 5:05 p.m. | 7:05 p.m. | B737 |
| WN6830 | Chicago (MDW) | Portland (PDX) | 6 p.m. | 7:55 p.m. | B737 |
| WN9000 | Chicago (MDW) | Portland (PDX) | 3:05 p.m. | 4:53 p.m. | |
| OZ245 | Chicago (MDW) | Portland (PDX) | 6:20 a.m. | 8:20 a.m. | |
| DWT159 | Chicago (MDW) | Portland (PDX) | 1:50 p.m. | 4:10 p.m. |
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