Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
137 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 05:50 | 11:45 | mon, thu, fri | WN2735 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:05 | 12:00 | tue, wed, sun | WN2321 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 11:34 | tue, wed, thu | 5X5975 | UPS | 3h 14m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 11:42 | fri, sat | 5X5975 | UPS | 3h 22m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:20 | 12:15 | sat | WN2735 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:20 | 12:29 | wed | 5X5975 | UPS | 4h 9m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 07:00 | 13:06 | daily | UA1693 | United Express | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:02 | 13:07 | daily | AS324 | Alaska SkyWest | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 08:30 | 14:25 | mon, thu, fri | WN4169 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 08:47 | 14:25 | fri | WN4169 | Southwest Airlines | 3h 38m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 08:55 | 14:50 | tue, wed | WN2735 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 09:20 | 15:15 | sat | WN4169 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 10:39 | 16:44 | tue, fri, sat | AA2515 | American Eagle | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:41 | 16:46 | mon, wed, thu, sun | AA2515 | American Eagle | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:48 | 16:56 | tue, wed | UA534 | United Express | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:54 | 17:02 | mon, thu, fri, sat, sun | UA534 | United Express | 4h 8m | 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 |
| 12:40 | 18:43 | daily | AA3303 | American Eagle | 4h 3m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:20 | 19:18 | mon, wed, thu, fri, sat, sun | AA3303 | American Eagle | 3h 58m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:24 | 19:29 | sat | AA1257 | American Eagle | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:30 | 19:30 | tue, wed | WN3186 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 13:35 | 19:35 | thu, fri | WN2149 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 13:50 | 19:45 | sun | WN2248 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 13:55 | 19:50 | sun | WN4170 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 14:12 | 20:25 | daily | UA1209 | United Express | 4h 13m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:30 | 20:25 | mon, tue, wed, thu, fri, sat | WN4170 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 15:24 | 21:29 | daily | AA1257 | American Eagle | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 17:35 | 23:39 | daily | AS376 | Alaska SkyWest | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 22:55 | 04:56 | mon, wed, thu, fri, sat, sun | UA2228 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:40 | 05:28 | fri | UA3924 | United Express | 3h 48m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:54 | 05:50 | daily | AA2977 | American Eagle | 3h 56m | 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 |
| 23:59 | 06:00 | daily | UA1490 | United Express | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |