Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
136 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 04:28 | 10:18 | daily | 5Y3736 | Atlas Air | 3h 50m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 05:30 | 11:30 | mon, thu, fri | WN407 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 11:28 | sat | 5X5975 | UPS | 3h 13m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 11:41 | wed | 5X5975 | UPS | 3h 26m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 11:34 | tue | 5X5975 | UPS | 3h 19m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 11:22 | thu | 5X5975 | UPS | 3h 7m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 13:17 | wed | 5X5975 | UPS | 5h 2m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 11:46 | wed | 5X5975 | UPS | 3h 31m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 11:33 | thu | 5X5975 | UPS | 3h 18m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 11:27 | sat | 5X5975 | UPS | 3h 12m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:15 | 12:15 | wed | WN407 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 11:25 | fri | 5X5975 | UPS | 3h 5m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 11:32 | wed, thu, fri, sat | 5X5975 | UPS | 3h 12m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 12:21 | tue | 5X5975 | UPS | 4h 1m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 11:35 | thu | 5X5975 | UPS | 3h 15m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 11:34 | tue, wed, thu, fri, sat | 5X5975 | UPS | 3h 14m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 11:42 | sat | 5X5975 | UPS | 3h 22m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:45 | 12:45 | sat | WN407 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:00 | daily | UA1693 | United Express | 4h 0m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:05 | daily | AS327 | Alaska Horizon | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:03 | mon, tue, thu, fri, sun | UA1693 | United Express | 4h 3m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:07 | daily | AS324 | Alaska Horizon | 4h 7m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:04 | wed, sun | UA1693 | United Express | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:05 | 13:05 | mon, tue, sun | UA1693 | United Express | 4h 0m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:50 | 16:56 | daily | UA534 | United Express | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:50 | 16:53 | sat | UA534 | United Express | 4h 3m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:51 | 16:55 | mon, wed, thu, sun | UA534 | United Express | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:56 | 16:57 | mon, tue, wed, sun | UA1335 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:00 | 17:01 | daily | UA1335 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:00 | 16:57 | tue, wed, sat | UA1335 | United Express | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:14 | 17:20 | mon, wed | AA1195 | American Airlines | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 12:10 | 18:05 | wed | WN3834 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 13:25 | 19:32 | tue, sat | AA2515 | American Airlines | 4h 7m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:30 | 19:25 | sun | WN3834 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 14:02 | 20:08 | mon, tue, thu, sat, sun | UA2360 | United Express | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:14 | 20:17 | mon, wed, sat | UA567 | United Express | 4h 3m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:58 | 21:04 | mon, wed, thu, fri, sun | AA2515 | American Airlines | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 15:24 | 21:29 | wed | AA1257 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 19:00 | 00:42 | sat | JL15 | Jet Linx Aviation | 3h 42m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:52 | 05:57 | daily | AA2366 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:55 | 06:52 | sun | UA2384 | United Express | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:58 | 05:55 | daily | UA2384 | United Express | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 06:00 | mon, thu, sun | UA2646 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 05:56 | daily | UA1490 | United Express | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |