Direct flights from Chicago Midway to Portland
19 nonstop flights a week on 1 airline. Zero layovers — one hop from MDW to PDX.
Flight time: about 3h41m nonstop
Which days does it fly?
When does it fly?
Departure times in Chicago Midway local time, from flights observed over the last 7 days.
| Flight | Departs | Duration | Days |
|---|---|---|---|
| Southwest SWA2809 | 10:18a | 3h40m | Fri, Sun |
| Southwest SWA2809 | 10:32a | 3h51m | Tue–Wed |
| Southwest SWA3928 | 10:41a | 3h42m | Sat |
| Southwest SWA2809 | 10:42a | 3h46m | Mon |
| Southwest SWA2809 | 11:20a | 3h34m | Thu |
| Southwest SWA4765 | 5:15p | 3h44m | Mon |
| Southwest SWA4765 | 5:29p | 3h34m | Fri |
| Southwest SWA4765 | 6:08p | 3h40m | Tue–Wed |
| Southwest SWA4765 | 7:20p | 3h32m | Thu |
| Southwest SWA2852 | 8:35p | 3h45m | Sat |
| Southwest SWA2852 | 10:02p | 3h42m | Tue, Fri |
| Southwest SWA2852 | 10:13p | 3h33m | Thu |
| Southwest SWA2852 | 10:32p | 3h34m | Wed |
| Southwest SWA2852 | 11:26p | 3h51m | Mon, Sun |
Southwest
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The route
One hop: MDW → PDXDrag to pan · scroll with ⌘/Ctrl to zoom · arrow keys when focused
Nonstop from Chicago Midway (MDW) to Portland (PDX)
Chicago Midway International Airport (MDW) has 19 nonstop flights a week to Portland (PDX), operated by Southwest. No layovers, no connections — one hop out of MDW 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 Chicago Midway to Portland?
The nonstop flight from Chicago Midway (MDW) to Portland (PDX) takes about 3h41m in the air, based on recently observed nonstop departures.
How long does it take to drive from Chicago Midway to Portland?
Driving from Chicago Midway to Portland takes about 31h 1m behind the wheel — roughly 2,137 miles, or about 3 days of real driving. The nonstop flight takes about 3h41m.