Portland to Chicago (PWM–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.
PWM–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 893 miles in approximately 2h 35m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 7 | 73H, 7S7 | 2h35-2h45 | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Portland
| Metric | PWM→MDW | PSM→MDW | MHT→MDW |
|---|---|---|---|
| Distance from PWM | – | 47 mi | 75 mi |
| Nonstop airlines | 1 | 3 | 1 |
| Weekly flights | 7 | 1 | 16 |
| Flight time | 2h 35m | 1h 59m | 2h 25m |
| Departure OTP | 60% | – | – |
Travel Essentials
PWM: EDT · MDW: CDT
When it's 6:00 PM in Portland, it's 5:00 PM in Chicago.
PWM–MDW Quick Facts
Frequently Asked Questions
Flights from PWM to MDW
Portland International Jetport (PWM) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 7 weekly departures, this is a regularly served route.
PWM to MDW Flight Duration and Schedule
Nonstop flight time from PWM to MDW is about 2 hours 35 minutes gate to gate. The route covers a distance of 893 miles (1,437 km). There are approximately 7 weekly flights outbound and 8 return, totaling 15 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Baltimore/Washington International Thurgood Marshall, Detroit Metropolitan Wayne County and Norfolk. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Portsmouth (PSM), Manchester (MHT) and Bedford (BED).