Using the online timetable is an easy way to look at all the direct flights Portland — Chicago
39 flights in a week
Departure and arrival times are local (Portland and Chicago)
| Departure | Arrival | Flight days | Flight | Airlines | Flight time | Airports | |
|---|---|---|---|---|---|---|---|
| 06:00 | 07:53 | mon, tue, wed, thu, fri, sun | UA1834 | United Express | 2h 53m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:00 | 07:51 | sat | UA1834 | United Express | 2h 51m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:10 | 08:05 | wed, thu, sat, sun | UA1834 | United Express | 2h 55m | Portland International Jetport — O'Hare International Airport | Select dates |
| 06:15 | 08:11 | daily | AA4391 | American Airlines | 2h 56m | Portland International Jetport — O'Hare International Airport | Select dates |
| 10:45 | 12:14 | wed | WN8805 | Southwest Airlines (Canyon Blue Retro Livery) | 2h 29m | Portland International Jetport — Chicago Midway International Airport | Select dates |
| 12:03 | 14:03 | daily | AA4741 | American Airlines | 3h 0m | Portland International Jetport — O'Hare International Airport | Select dates |
| 13:59 | 15:59 | sat | AA4477 | American Airlines | 3h 0m | Portland International Jetport — O'Hare International Airport | Select dates |
| 14:10 | 16:11 | sat | AA4477 | American Airlines | 3h 1m | Portland International Jetport — O'Hare International Airport | Select dates |
| 16:56 | 18:53 | wed, thu, sat | UA2466 | United Express | 2h 57m | Portland International Jetport — O'Hare International Airport | Select dates |
| 18:20 | 20:25 | sat | UA5327 | United Express | 3h 5m | Portland International Jetport — O'Hare International Airport | Select dates |
| 18:55 | 20:30 | tue, wed | WN4338 | Southwest Airlines (Canyon Blue Retro Livery) | 2h 35m | Portland International Jetport — Chicago Midway International Airport | Select dates |
| 19:10 | 20:45 | sat | WN4338 | Southwest Airlines (Canyon Blue Retro Livery) | 2h 35m | Portland International Jetport — Chicago Midway International Airport | Select dates |
| 19:40 | 21:15 | mon, thu, fri | WN4338 | Southwest Airlines (Canyon Blue Retro Livery) | 2h 35m | Portland International Jetport — Chicago Midway International Airport | Select dates |
| 19:55 | 21:30 | sun | WN4338 | Southwest Airlines (Canyon Blue Retro Livery) | 2h 35m | Portland International Jetport — Chicago Midway International Airport | Select dates |