Using the online timetable is an easy way to look at all the direct flights Chicago — Portland
144 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 |
| 02:36 | 04:28 | tue, wed, thu, fri | 5X970 | UPS | 3h 52m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 02:36 | 04:40 | tue | 5X970 | UPS | 4h 4m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 07:00 | 09:32 | mon, thu, fri, sat | AS413 | Alaska Horizon | 4h 32m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:00 | 09:39 | mon, thu, fri, sat, sun | AS413 | Alaska Horizon | 4h 39m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:00 | 09:32 | thu | AS413 | AlphaSky | 4h 32m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:00 | 09:39 | mon, thu, fri | AS413 | AlphaSky | 4h 39m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:09 | 09:31 | daily | AA3272 | American Eagle | 4h 22m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:10 | 09:39 | mon, thu, sun | AA3272 | American Eagle | 4h 29m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:30 | 09:59 | sat | AA3272 | American Eagle | 4h 29m | O'Hare International Airport — Portland International Airport | Select dates |
| 07:40 | 10:00 | wed | WN4004 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 08:10 | 10:47 | tue, wed | AA563 | American Eagle | 4h 37m | O'Hare International Airport — Portland International Airport | Select dates |
| 08:14 | 10:48 | tue, wed | AA563 | American Eagle | 4h 34m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:05 | 11:41 | thu, fri | UA1994 | United Express | 4h 36m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:05 | 11:48 | daily | UA1994 | United Express | 4h 43m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:10 | 11:43 | daily | UA2254 | United Express | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 09:40 | 12:15 | sat | WN2039 | Southwest Airlines | 4h 35m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 09:57 | 12:38 | mon, fri, sun | AA563 | American Eagle | 4h 41m | O'Hare International Airport — Portland International Airport | Select dates |
| 10:00 | 12:36 | tue, thu, fri, sat, sun | AA563 | American Eagle | 4h 36m | O'Hare International Airport — Portland International Airport | Select dates |
| 10:55 | 13:15 | fri | WN1491 | Southwest Airlines | 4h 20m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 12:45 | 15:15 | tue | UA1830 | United Express | 4h 30m | O'Hare International Airport — Portland International Airport | Select dates |
| 13:30 | 16:05 | thu | UA463 | United Express | 4h 35m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:04 | 16:37 | tue, wed, fri, sat, sun | AS325 | Alaska Horizon | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:04 | 16:37 | fri | AS325 | AlphaSky | 4h 33m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:05 | 16:41 | mon, tue, wed | AS325 | AlphaSky | 4h 36m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:05 | 16:41 | mon, tue, wed, thu, sun | AS325 | Alaska Horizon | 4h 36m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:05 | 16:48 | mon, thu, fri, sun | AS325 | Alaska Horizon | 4h 43m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:07 | 16:37 | daily | AS325 | Alaska Horizon | 4h 30m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:07 | 16:04 | tue, wed, thu | 5X2994 | UPS | 3h 57m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 14:10 | 16:50 | sat, sun | AS325 | Alaska Horizon | 4h 40m | O'Hare International Airport — Portland International Airport | Select dates |
| 14:15 | 16:23 | sat | WN9001 | Southwest Airlines | 4h 8m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 14:15 | 16:45 | sat | WN519 | Southwest Airlines | 4h 30m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 14:26 | 16:37 | mon | 5X2988 | UPS | 4h 11m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 14:26 | 16:19 | mon | 5X2988 | UPS | 3h 53m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 15:45 | 17:38 | thu | 5X2040 | UPS | 3h 53m | Chicago Rockford International Airport — Portland International Airport | Select dates |
| 16:05 | 18:31 | mon, tue, wed, fri, sun | UA2494 | United Express | 4h 26m | O'Hare International Airport — Portland International Airport | Select dates |
| 16:05 | 18:40 | mon, wed, thu, sat, sun | UA2207 | United Express | 4h 35m | O'Hare International Airport — Portland International Airport | Select dates |
| 16:10 | 18:45 | mon, thu, sat, sun | UA2331 | United Express | 4h 35m | O'Hare International Airport — Portland International Airport | Select dates |
| 16:50 | 19:20 | mon, tue, wed, thu | WN2039 | Southwest Airlines | 4h 30m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 18:30 | 20:55 | sun | WN3337 | Southwest Airlines | 4h 25m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 19:30 | 22:00 | mon | WN2039 | Southwest Airlines | 4h 30m | Chicago Midway International Airport — Portland International Airport | Select dates |
| 19:37 | 22:15 | mon, tue, wed, thu, fri, sat | UA2059 | United Express | 4h 38m | O'Hare International Airport — Portland International Airport | Select dates |
| 19:48 | 22:26 | sun | UA2059 | United Express | 4h 38m | O'Hare International Airport — Portland International Airport | Select dates |
| 19:58 | 22:40 | thu, fri | UA2059 | United Express | 4h 42m | O'Hare International Airport — Portland International Airport | Select dates |
| 20:32 | 23:06 | daily | AA3028 | American Eagle | 4h 34m | O'Hare International Airport — Portland International Airport | Select dates |
| 21:50 | 00:20 | mon, thu, fri, sat, sun | WN2039 | Southwest Airlines | 4h 30m | Chicago Midway International Airport — Portland International Airport | Select dates |