Direct flights from Portland to Chicago
7 nonstop flights a week on 1 airline. Zero layovers — one hop from PWM to MDW.
Flight time: about 2h5m 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 |
|---|---|---|---|
| Southwest SWA2464 | 6:51a | 2h5m | Sun |
| Southwest SWA3415 | 7:41a | 2h3m | Tue–Wed |
| Southwest SWA3415 | 7:49a | 2h8m | Thu–Fri |
| Southwest SWA3415 | 9:06a | 2h3m | Mon |
| Southwest SWA3642 | 5:37p | 2h13m | Sat |
Southwest
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The route
One hop: PWM → MDWDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Portland (PWM) to Chicago (MDW)
Portland International Jetport (PWM) has 7 nonstop flights a week to Chicago (MDW), operated by Southwest. 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 July 2026 from observed departures.
Route data updated July 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 (MDW) takes about 2h5m 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 2h5m.