Using the online timetable is an easy way to look at all the direct flights Chicago — Portland
107 flights in a week
Departure and arrival times are local (Chicago and Portland)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 02:36 | 04:28 | tue, wed, thu, fri | 5X970 | UPS | 3h 52m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 02:36 | 04:33 | thu | 5X970 | UPS | 3h 57m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 08:15 | 10:48 | mon, tue, wed, thu, fri, sun | AA820 | American Eagle | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 08:23 | 10:56 | sun | AA820 | American Eagle | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 08:25 | 10:58 | mon, tue, wed, thu, sun | AA820 | American Eagle | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 08:29 | 11:02 | fri | AA820 | American Eagle | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:06 | 11:53 | thu | UA1994 | United Express | 4h 47m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:06 | 11:51 | daily | UA1994 | United Express | 4h 45m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:10 | 11:57 | tue, wed | UA1994 | United Express | 4h 47m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:10 | 11:55 | daily | UA1994 | United Express | 4h 45m | O'Hare International Airport — Portland International Airport | Select dates |
| 10:05 | 12:30 | sun | WN3975 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 10:30 | 12:50 | mon, tue, wed, thu, fri | WN3975 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 11:00 | 13:20 | sat | WN3975 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 11:20 | 13:53 | tue, wed | AA442 | American Eagle | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:05 | 14:30 | thu, fri | WN236 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 12:40 | 15:09 | tue, wed, sun | UA1554 | United Express | 4h 29m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:40 | 15:03 | mon | UA1554 | United Express | 4h 23m | O'Hare International Airport — Portland International Airport | Select dates |
| 12:45 | 15:27 | tue, wed | UA379 | United Express | 4h 42m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:07 | 16:04 | mon, tue, wed | 5X2986 | UPS | 3h 57m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 14:07 | 16:00 | tue, wed, thu | 5X2986 | UPS | 3h 53m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 14:07 | 16:50 | daily | AS325 | Alaska Airlines | 4h 43m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:09 | 16:50 | mon, wed | AS325 | Alaska Airlines | 4h 41m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:40 | 16:33 | sun | 5X5986 | UPS | 3h 53m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 15:35 | 18:00 | tue, wed | WN1691 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 16:15 | 18:56 | daily | UA2850 | United Express | 4h 41m | O'Hare International Airport — Portland International Airport | Select dates |
| 16:15 | 18:49 | wed, thu, fri, sat | UA2850 | United Express | 4h 34m | O'Hare International Airport — Portland International Airport | Select dates |
| 16:40 | 19:14 | daily | UA1920 | United Express | 4h 34m | O'Hare International Airport — Portland International Airport | Select dates |
| 17:54 | 20:27 | mon, tue | AA819 | American Eagle | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 20:04 | 22:45 | daily | UA1531 | United Express | 4h 41m | O'Hare International Airport — Portland International Airport | Select dates |
| 20:45 | 23:10 | tue, wed | WN3976 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 21:40 | 00:05 | mon | WN3976 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 21:44 | 00:15 | mon, thu, fri, sun | AA2128 | American Eagle | 4h 31m | O'Hare International Airport — Portland International Airport | Select dates |
| 21:49 | 00:20 | wed | AA2128 | American Eagle | 4h 31m | O'Hare International Airport — Portland International Airport | Select dates |
| 22:20 | 00:45 | fri | WN3976 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 22:30 | 00:55 | sun | WN3976 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |