Portland to Chicago (PDX–MDW) — Airlines, Schedules & Connections
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No nonstop flights on this route. connecting options below.
PDX–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,747 miles in approximately 3h 50m. Beyond nonstop, 66 hubs offer 1-stop connections.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 28 | 737, 73H, 7M8 | 3h50-3h55 | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Portland
| Metric | PDX→MDW | EUG→MDW | SEA→MDW |
|---|---|---|---|
| Distance from PDX | – | 106 mi | 129 mi |
| Nonstop airlines | 1 | 1 | 1 |
| Weekly flights | 28 | 1 | 28 |
| Flight time | 3h 50m | 4h 27m | 4h |
| Departure OTP | 91% | – | – |
Travel Essentials
PDX: MDT · MDW: CDT
When it's 6:00 PM in Portland, it's 7:00 PM in Chicago.
PDX–MDW Quick Facts
Frequently Asked Questions
Flights from PDX to MDW
Portland International Airport (PDX) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 28 weekly departures, this is a heavily served route.
PDX to MDW Flight Duration and Schedule
Nonstop flight time from PDX to MDW ranges from 3 hours 50 minutes to 3 hours 55 minutes. The route covers a distance of 1,747 miles (2,811 km). There are approximately 28 weekly flights outbound and 28 return, totaling 56 flights per week in both directions.
Connecting Options and Alternatives
66 one-stop connections are available, with the fastest taking approximately 5 hours via BZN. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Eugene (EUG) and Seattle (SEA).