Cheap Flights from CHI to PDX
The Cheapest Round-trip Tickets from Chicago to Portland
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 15 October 2026 | 22 October 2026 | Direct |  | RT from 284 |
The Cheapest Flights for this Month from Chicago to Portland
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 9 September 2026 | 14 September 2026 | 1 Stop | | RT from 375 |
| 19 September 2026 | 21 September 2026 | 1 Stop |  | RT from 342 |
| 2 October 2026 | 5 October 2026 | 1 Stop | | RT from 300 |
| 15 October 2026 | 22 October 2026 | 1 Stop | | RT from 284 |
| 15 December 2026 | 20 December 2026 | 1 Stop |  | RT from 375 |
The Cheapest Flights from Chicago to Portland for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 19 September 2026 | 21 September 2026 | 1 Stop | | RT from 342 |
| 15 October 2026 | 22 October 2026 | 1 Stop | | RT from 284 |
| 15 December 2026 | 20 December 2026 | 1 Stop | | RT from 375 |