Direct flights from Portland to Chicago
42 nonstop flights a week on 2 airlines. Zero layovers — one hop from PWM to ORD.
Flight time: about 2h9m nonstop
Which days does it fly?
When does it fly?
Departure times in Portland local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| United UAL723 | 6:04a | 2h9m | Wed |
| United UAL723 | 6:10a | 2h16m | Mon, Tue, Fri, Sat |
| United UAL723 | 6:18a | 2h18m | Thu, Sun |
| Republic Airways RPA4499 | 6:38a | 1h55m | Mon, Thu, Fri |
| Republic Airways RPA4499 | 6:50a | 1h44m | Sun |
| Republic Airways RPA4499 | 7:33a | 1h44m | Wed |
| Republic Airways RPA3544 | 8:06a | 2h2m | Mon, Thu, Fri, Sun |
| Republic Airways RPA3544 | 8:18a | 2h2m | Sat |
| Republic Airways RPA3544 | 8:31a | 2h2m | Wed |
| Republic Airways RPA3544 | 8:37a | 2h2m | Tue |
| Republic Airways RPA4499 | 9:24a | 2h | Tue |
| Republic Airways RPA4499 | 11:40a | 1h35m | Sat |
| Republic Airways RPA4741 | 12:20p | 2h13m | Tue |
| American AAL2717 | 2:11p | 2h18m | Wed, Fri, Sat |
| American AAL2717 | 2:15p | 2h43m | Mon |
| American AAL2717 | 2:29p | 2h50m | Thu |
| United UAL1828 | 5:02p | 2h15m | Tue, Thu, Fri |
| United UAL1828 | 5:08p | 2h14m | Mon |
| United UAL1828 | 5:20p | 2h15m | Wed, Sun |
| Republic Airways RPA4741 | 5:50p | 1h52m | Mon, Thu, Fri, Sun |
| Republic Airways RPA4741 | 6:01p | 2h6m | Sat |
| Republic Airways RPA4741 | 6:07p | 1h41m | Wed |
| Republic Airways RPA4729 | 6:18p | 2h23m | Tue |
| United UAL1828 | 6:57p | 2h13m | Sat |
| American AAL2717 | 7:25p | 2h29m | Sun |
American
UnitedThe route
One hop: PWM → ORDDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Portland (PWM) to Chicago (ORD)
Portland International Jetport (PWM) has 42 nonstop flights a week to Chicago (ORD), operated by American and United. No layovers, no connections — one hop out of PWM and you're there.
This route flies every day of the week, so any travel day works. Route data updated September 2026 from observed departures.
Route data updated September 2026 from observed flight departures. Schedules change — always confirm with the airline before booking.
How long is the flight from Portland to Chicago?
The nonstop flight from Portland (PWM) to Chicago (ORD) takes about 2h9m in the air, based on recently observed nonstop departures.
How long does it take to drive from Portland to Chicago?
Driving from Portland to Chicago takes about 16h 11m behind the wheel — roughly 1,085 miles, or about 2 days of real driving. The nonstop flight takes about 2h9m.