Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
97 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 04:28 | 09:50 | thu | 5Y3736 | Atlas Air | 3h 22m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 04:28 | 09:46 | fri | 5Y3736 | Atlas Air | 3h 18m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 04:28 | 10:14 | fri | 5Y3736 | Atlas Air | 3h 46m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 04:28 | 09:47 | sat | 5Y3736 | Atlas Air | 3h 19m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 04:28 | 10:15 | fri, sun | 5Y3736 | Atlas Air | 3h 47m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 04:28 | 09:56 | sun | 5Y3736 | Atlas Air | 3h 28m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 05:30 | 11:31 | fri | AS9341 | Alaska Horizon | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 06:22 | 11:34 | thu | 5X2375 | UPS | 3h 12m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 06:30 | 12:20 | sat | WN574 | Southwest Airlines | 3h 50m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:30 | 12:30 | fri | WN5919 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:40 | 12:35 | sun | WN4141 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:45 | 12:35 | sat | WN5919 | Southwest Airlines | 3h 50m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 06:50 | 12:45 | tue, wed | WN5919 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 12:55 | mon | WN367 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:00 | 13:06 | daily | AS324 | Alaska Horizon | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:00 | 13:02 | daily | UA1693 | United Airlines | 4h 2m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:15 | 13:10 | sun | WN5225 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:20 | 13:20 | tue, wed, sun | WN5919 | Southwest Airlines | 4h 0m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 07:43 | 13:53 | tue, wed, fri, sun | AS324 | Alaska Horizon | 4h 10m | Portland International Airport — O'Hare International Airport | Select dates |
| 07:45 | 13:40 | sat | WN1799 | Southwest Airlines | 3h 55m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 10:05 | 15:55 | sat | WN1071 | Southwest Airlines | 3h 50m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 10:40 | 16:41 | sat | UA1444 | United Airlines | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:48 | 16:48 | thu | UA1444 | United Airlines | 4h 0m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:58 | 16:59 | mon, tue, wed, thu | UA1444 | United Airlines | 4h 1m | Portland International Airport — O'Hare International Airport | Select dates |
| 10:58 | 17:02 | daily | UA357 | United Airlines | 4h 4m | Portland International Airport — O'Hare International Airport | Select dates |
| 11:12 | 17:10 | mon, tue, wed, thu, sat, sun | UA357 | United Airlines | 3h 58m | Portland International Airport — O'Hare International Airport | Select dates |
| 12:00 | 17:50 | wed | WN1071 | Southwest Airlines | 3h 50m | Portland International Airport — Chicago Midway International Airport | Select dates |
| 13:32 | 19:30 | mon, thu, fri, sat, sun | AA2232 | American Airlines | 3h 58m | Portland International Airport — O'Hare International Airport | Select dates |
| 14:14 | 20:19 | mon, tue, thu, fri, sat | UA321 | United Airlines | 4h 5m | Portland International Airport — O'Hare International Airport | Select dates |
| 19:00 | 00:22 | tue, wed, thu | 5X971 | UPS | 3h 22m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 19:00 | 00:18 | mon, tue | 5X971 | UPS | 3h 18m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 19:00 | 03:33 | fri | 5X971 | UPS | 6h 33m | Portland International Airport — Chicago Rockford International Airport | Select dates |
| 22:24 | 04:45 | mon, tue, wed, thu, fri, sat | AS340 | Alaska Horizon | 4h 21m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:21 | 06:19 | sun | UA2275 | United Airlines | 3h 58m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:50 | 05:56 | daily | UA1490 | United Airlines | 4h 6m | Portland International Airport — O'Hare International Airport | Select dates |
| 23:59 | 05:57 | daily | UA2275 | United Airlines | 3h 58m | Portland International Airport — O'Hare International Airport | Select dates |