Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
62 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:00 | 11:55 | sat | WN2884 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:00 | 12:15 | daily | AA820 | American Airlines | 4h 15m | Portland International Airport — O'Hare International Airport | Select dates |
| 06:20 | 11:31 | tue, wed, thu | 5X5975 | UPS | 3h 11m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:30 | 12:25 | mon, tue, wed, thu, fri, sun | WN2884 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 12:40 | mon, thu, fri, sun | WN930 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:05 | daily | UA2306 | United Express | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:05 | 13:10 | mon, tue, thu, fri, sun | AS324 | Alaska Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:47 | 16:48 | daily | UA2321 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:50 | 16:52 | daily | UA534 | United Express | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:52 | 16:54 | tue, wed, thu, fri, sat, sun | UA534 | United Express | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:52 | 16:56 | mon | UA534 | United Express | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:02 | 17:05 | sat, sun | UA534 | United Express | 4h 3m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:43 | 21:02 | tue, wed | AA544 | American Airlines | 4h 19m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 06:00 | mon, tue, fri, sat | UA1490 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |