Portland to Chicago (PDX–MDW) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
PDX–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,747 miles in approximately 3h 55m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 34 | 73H, 7M8, B38M | 3h50-4h | – | – |
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 | 34 | – | 35 |
| Flight time | 3h 55m | 4h 27m | 3h 54m |
| Departure OTP | 100% | – | – |
Travel Essentials
PDX: PDT · MDW: CDT
When it's 6:00 PM in Portland, it's 8:00 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 34 weekly departures, this is a heavily served route.
PDX to MDW Flight Duration and Schedule
Nonstop flight time from PDX to MDW is about 3 hours 55 minutes gate to gate. The route covers a distance of 1,747 miles (2,811 km). There are approximately 34 weekly flights outbound and 33 return, totaling 67 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Boise Air Terminal/Gowen Field, Kansas City and Salt Lake City. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Eugene (EUG), Seattle (SEA) and Seattle (BFI).