Using the online timetable is an easy way to look at all the direct flights Chicago — Portland
118 flights in a week
Departure and arrival times are local (Chicago and Portland)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 02:36 | 04:44 | tue | 5X970 | UPS | 4h 8m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 02:36 | 04:19 | wed | 5X970 | UPS | 3h 43m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 02:36 | 04:25 | tue, wed, thu, fri | 5X970 | UPS | 3h 49m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 07:00 | 09:25 | daily | AS413 | Alaska Airlines | 4h 25m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:10 | 09:42 | mon, thu, fri, sat, sun | UA1100 | United Airlines | 4h 32m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:25 | 09:51 | mon, wed, thu, sun | AA3320 | American Eagle | 4h 26m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:25 | 09:49 | mon, tue, fri, sat | AA3320 | American Eagle | 4h 24m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:45 | 10:05 | sat | WN2121 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 07:50 | 10:10 | tue, wed | WN2121 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 08:15 | 10:35 | sun | WN2121 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 09:10 | 11:43 | daily | UA2254 | United Airlines | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:10 | 11:30 | mon | WN3874 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 10:06 | 12:34 | sat | AA1257 | American Eagle | 4h 28m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:06 | 14:25 | daily | AA2545 | American Eagle | 4h 19m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:08 | 14:34 | daily | AA1257 | American Eagle | 4h 26m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:45 | 15:15 | tue | UA1830 | United Airlines | 4h 30m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:46 | 15:14 | daily | UA2616 | United Airlines | 4h 28m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:49 | 15:14 | fri | UA2616 | United Airlines | 4h 25m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:03 | 16:35 | mon, tue, thu, fri, sun | AS325 | Alaska Airlines | 4h 32m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:04 | 16:30 | sat | AS325 | Alaska Airlines | 4h 26m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:07 | 15:55 | tue, wed, thu, fri, sat | 5X2994 | UPS | 3h 48m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 14:09 | 16:35 | mon, tue, wed, thu, fri, sun | AS325 | Alaska Airlines | 4h 26m | O'Hare International Airport — Portland International Airport | Select dates |
| 15:50 | 18:05 | tue, wed | WN1766 | Southwest Airlines | 4h 15m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 15:55 | 18:15 | mon, thu, fri | WN3698 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 16:00 | 18:20 | sat | WN3698 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 16:05 | 18:25 | tue, wed | WN1656 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 16:13 | 18:45 | daily | UA580 | United Airlines | 4h 32m | O'Hare International Airport — Portland International Airport | Select dates |
| 19:55 | 22:29 | daily | UA2059 | United Airlines | 4h 34m | O'Hare International Airport — Portland International Airport | Select dates |
| 20:25 | 23:04 | daily | AA2977 | American Eagle | 4h 39m | O'Hare International Airport — Portland International Airport | Select dates |
| 20:50 | 23:05 | mon, thu, fri | WN1766 | Southwest Airlines | 4h 15m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 21:10 | 23:35 | sat | WN1656 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 21:30 | 23:55 | tue | WN3874 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 22:05 | 00:25 | mon, thu, fri | WN1656 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 22:25 | 00:45 | mon, sun | WN1656 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |