Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
108 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:00 | 10:55 | thu | WN3617 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 05:22 | 10:41 | mon | 5X9785 | UPS | 3h 19m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 05:30 | 10:41 | mon | 5X2985 | UPS | 3h 11m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:00 | 11:55 | tue, wed, sat, sun | WN4016 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:15 | 12:10 | mon, tue, wed, thu, fri | WN4016 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway 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 | thu, fri, sun | WN4016 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:02 | daily | UA2635 | United Express | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:09 | daily | AS324 | Alaska Airlines | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:04 | 13:09 | mon | AS324 | Alaska Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:07 | 13:14 | fri, sat, sun | AS324 | Alaska Airlines | 4h 7m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:45 | 13:40 | sat | WN4013 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 08:35 | 14:43 | mon, thu | UA2074 | United Express | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:20 | 16:15 | sat | WN4016 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway 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 |
| 11:43 | 17:55 | tue | AA563 | American Eagle | 4h 12m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:16 | 19:33 | mon, wed, thu, fri, sat, sun | AA2515 | American Eagle | 4h 17m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:23 | 19:30 | tue | AA2515 | American Eagle | 4h 7m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:25 | 19:20 | wed | WN298 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 13:26 | 19:41 | mon, thu, sun | AA563 | American Eagle | 4h 15m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:28 | 19:43 | mon, sun | AA563 | American Eagle | 4h 15m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:28 | 19:46 | sat, sun | AA563 | American Eagle | 4h 18m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:35 | 20:25 | mon, thu | WN1603 | Southwest Airlines | 3h 50m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 15:02 | 21:24 | sat | AA563 | American Eagle | 4h 22m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:00 | 05:02 | mon, thu, fri, sat, sun | AS376 | Alaska Airlines | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:01 | 05:03 | tue, sat | AS376 | Alaska Airlines | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:55 | 05:56 | sat | UA1490 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:58 | 05:53 | daily | AA565 | American Eagle | 3h 55m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:58 | 04:53 | sun | AA565 | American Eagle | 3h 55m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 06:00 | daily | UA1490 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 05:54 | mon, wed, thu, sun | UA1490 | United Express | 3h 55m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 05:52 | daily | UA1490 | United Express | 3h 53m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 04:52 | sun | UA1490 | United Express | 3h 53m | Portland International Airport — O'Hare International Airport | Select dates |