Below you can find the flight schedule for Portland, Oregon to Chicago for April. If you are looking for flight fares, please check the cheap flights Portland, Oregon to Chicago, or you can use the search form at the top.
| Airline | Flight number | Departure | Arrival | Flight time |
| Alaska Airlines | AS696 | 07:00 | 13:10 | 4h 10m |
| Alaska Airlines | AS686 | 09:50 | 15:55 | 4h 5m |
| Alaska Airlines | AS690 | 17:45 | 23:40 | 3h 55m |
| Austrian Airlines | OS457 | 20:20 | 21:40 | 23h 20m |
| British Airways | BA1442 | 08:45 | 10:10 | 1h 25m |
| British Airways | BA984 | 12:50 | 15:40 | 50m |
| Lufthansa | LH1490 | 09:30 | 12:55 | 1h 25m |
| Lufthansa | LH1041 | 17:55 | 19:10 | 1h 15m |
| Lufthansa | LH1681 | 20:20 | 21:35 | 23h 15m |
| United Airlines | UA1504 | 00:30 | 06:28 | 3h 58m |
| United Airlines | UA2220 | 00:37 | 06:44 | 4h 7m |
| United Airlines | UA457 | 05:05 | 07:04 | 1h 59m |
| United Airlines | UA605 | 06:00 | 09:06 | 1h 6m |
| United Airlines | UA1693 | 06:55 | 12:58 | 4h 3m |
| United Airlines | UA1041 | 07:00 | 12:58 | 3h 58m |
| United Airlines | UA570 | 07:00 | 12:53 | 3h 53m |
| United Airlines | UA2334 | 07:00 | 09:53 | 53m |
| United Airlines | UA1253 | 07:00 | 09:34 | 34m |
| United Airlines | UA1617 | 07:05 | 09:01 | 1h 56m |
| United Airlines | UA1681 | 07:50 | 10:00 | 10m |
| United Airlines | UA1134 | 08:15 | 16:47 | 6h 32m |
| United Airlines | UA2239 | 09:01 | 10:42 | 23h 41m |
| United Airlines | UA2287 | 11:13 | 17:10 | 3h 57m |
| United Airlines | UA2177 | 12:50 | 17:00 | 2h 10m |
| United Airlines | UA766 | 23:12 | 05:05 | 3h 53m |
| United Airlines | UA1490 | 23:46 | 05:43 | 3h 57m |
Cheap flights Portland, Oregon to Chicago.
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