Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
104 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:20 | 11:15 | mon, thu, fri, sat | WN280 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 05:25 | 11:20 | tue, wed | WN280 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 12:10 | sun | WN280 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 11:35 | tue, thu | 5X5975 | UPS | 3h 15m | Portland International Airport — Chicago Rockford 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 | tue, wed | WN2884 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 12:40 | mon | WN2884 | 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 |
| 07:00 | 13:04 | daily | UA2294 | United Express | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:11 | tue, wed, thu, fri, sun | AS324 | Alaska Airlines | 4h 11m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:09 | mon, tue | UA1496 | United Express | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:11 | sun | UA1496 | United Express | 4h 11m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:03 | 13:13 | mon, wed, sat | AS324 | Alaska Airlines | 4h 10m | 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 |
| 11:00 | 16:58 | daily | UA1641 | United Express | 3h 58m | 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 |
| 11:46 | 17:55 | mon, tue, wed, thu, sun | AA820 | American Eagle | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:48 | 17:57 | mon, tue, wed, thu, sun | AA820 | American Eagle | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:52 | 18:01 | fri | AA820 | American Eagle | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:28 | 06:20 | sun | UA2293 | United Express | 3h 52m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:35 | 05:32 | daily | AA1508 | American Eagle | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:35 | 06:32 | sun | AA1508 | American Eagle | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:55 | 05:45 | daily | WN4161 | Southwest Airlines | 3h 50m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 23:59 | 05:53 | daily | UA2293 | United Express | 3h 54m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 05:56 | daily | AA1508 | American Eagle | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |