Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
171 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:00 | 12:00 | tue, wed | WN2678 | Southwest Airlines | 4h 0m | 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 |
| 06:05 | 12:10 | wed, sat | AA2395 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 06:05 | 12:05 | sun | WN2678 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:07 | 12:12 | tue, wed, sun | AA2395 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 06:10 | 12:10 | thu, fri | WN2678 | Southwest Airlines | 4h 0m | 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 |
| 07:00 | 13:06 | daily | UA1045 | United Airlines | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:07 | sat, sun | AA3329 | American Airlines | 4h 7m | 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 |
| 07:00 | 13:08 | daily | UA1693 | United Airlines | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:11 | tue, wed | AS324 | Alaska Airlines | 4h 11m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:02 | 13:07 | mon, tue, thu, fri, sat, sun | AS324 | Alaska Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 08:15 | 14:10 | fri | WN3780 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway 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 |
| 08:30 | 14:38 | mon, tue, thu, fri, sat | UA1369 | United Airlines | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 08:47 | 14:25 | fri | WN4169 | Southwest Airlines | 3h 38m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 09:20 | 15:15 | tue, wed | WN2668 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 10:23 | 16:28 | mon, thu, sun | AA2515 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:23 | 16:25 | sat | AA2515 | American Airlines | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:28 | 16:37 | thu | AA2889 | American Airlines | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:35 | 16:35 | sat | WN2149 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 10:38 | 16:47 | tue, wed | AA2515 | American Airlines | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:39 | 16:44 | tue, fri, sat | AA2515 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:41 | 16:46 | mon, wed, thu, sun | AA2515 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:45 | 17:00 | sun | AA2889 | American Airlines | 4h 15m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:48 | 16:56 | tue, wed | UA534 | United Airlines | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:51 | 16:59 | mon, wed, thu, fri, sat, sun | UA462 | United Airlines | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:54 | 17:02 | mon, thu, fri, sat, sun | UA534 | United Airlines | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:56 | 16:57 | mon, tue, wed, sun | UA1335 | United Airlines | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:00 | 17:01 | daily | UA1335 | United Airlines | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:00 | 16:57 | tue, wed, sat | UA1335 | United Airlines | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:18 | 17:28 | fri, sat | AA2889 | American Airlines | 4h 10m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:09 | 19:25 | sun | AA2515 | American Airlines | 4h 16m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:12 | 19:28 | sat | AA2515 | American Airlines | 4h 16m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:20 | 19:18 | daily | AA3303 | American Airlines | 3h 58m | Portland International Airport — O'Hare International Airport | Select dates |
| 13:24 | 19:29 | sat | AA1257 | American Airlines | 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 |
| 14:12 | 20:25 | daily | UA1492 | United Airlines | 4h 13m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:15 | 20:25 | mon, sat | UA740 | United Airlines | 4h 10m | Portland International Airport — O'Hare International Airport | Select dates |
| 15:24 | 21:29 | daily | AA1257 | American Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 17:35 | 23:39 | mon, tue | AS376 | Alaska Airlines | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 17:50 | 23:59 | sat | AS370 | Alaska Airlines | 4h 9m | Portland International Airport — O'Hare International Airport | Select dates |
| 17:50 | 00:04 | sat, sun | AS370 | Alaska Airlines | 4h 14m | Portland International Airport — O'Hare International Airport | Select dates |
| 18:00 | 00:08 | sun | UA3909 | United Airlines | 4h 8m | Portland International Airport — O'Hare International Airport | Select dates |
| 22:55 | 05:00 | mon, fri | AS376 | Alaska Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:00 | 05:00 | mon, thu, fri, sat, sun | AS376 | Alaska Airlines | 4h 0m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:40 | 05:28 | fri | UA3924 | United Airlines | 3h 48m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:54 | 05:50 | daily | AA2977 | American Airlines | 3h 56m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 05:56 | daily | UA1490 | United Airlines | 3h 57m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 06:00 | daily | UA1490 | United Airlines | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |