Cheap flights from Portland to Chicago
Find cheap Chicago to Portland flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Portland.
Portland to Chicago flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Portland (PDX) - Chicago (CHI) | 2026-09-04 | 2026-09-06 | 380 USD | 8 hours 10 minutes | Direct | 2026-08-09T18:59:51 |
Portland to Chicago flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| WN4366 | Portland (PDX) | Chicago (MDW) | 8:55 a.m. | 12:35 p.m. | B737 |
| WN3358 | Portland (PDX) | Chicago (MDW) | 9:55 p.m. | 10:50 p.m. | B737 |
| DE1235 | Portland (PDX) | Chicago (MDW) | 10:35 a.m. | 12:40 p.m. | 767 |
| WN6831 | Portland (PDX) | Chicago (MDW) | 8:05 a.m. | 10:15 a.m. | B737 |
| K9167 | Portland (PDX) | Chicago (MDW) | 2 p.m. | 2:43 p.m. | LJ35 |
| AV719 | Portland (PDX) | Chicago (MDW) | 7:40 a.m. | 1:15 p.m. | AT7 |
| AH1159 | Portland (PDX) | Chicago (MDW) | 7:05 a.m. | 9:10 a.m. | 738 |
Popular Flights Searchs
- Domestic Destinations
- International Destinations