Cheap Flights from CHI to PDX
The Cheapest Round-trip Tickets from Chicago to Portland
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 23 May 2026 | 25 May 2026 | Direct |  | RT from 138 |
The Cheapest Flights for this Month from Chicago to Portland
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 21 February 2026 | 24 February 2026 | Direct |  | RT from 467 |
| 28 February 2026 | 10 March 2026 | Direct | | RT from 140 |
| 27 March 2026 | 31 March 2026 | 1 Stop |  | RT from 172 |
| 22 May 2026 | 25 May 2026 | 1 Stop |  | RT from 221 |
| 23 May 2026 | 25 May 2026 | Direct | | RT from 138 |
| 23 July 2026 | 28 July 2026 | Direct | | RT from 255 |
The Cheapest Flights from Chicago to Portland for the Year Ahead
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 28 February 2026 | 10 March 2026 | Direct | | RT from 140 |
| 27 March 2026 | 31 March 2026 | 1 Stop | | RT from 172 |
| 23 May 2026 | 25 May 2026 | Direct | | RT from 138 |
| 23 July 2026 | 28 July 2026 | Direct | | RT from 255 |