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 | 13 | 73H, 7M8, 7S7, B38M | 2h35-2h45 | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Portland
| Metric | PWM→MDW | PSM→MDW | RKD→MDW |
|---|---|---|---|
| Distance from PWM | – | 47 mi | 67 mi |
| Nonstop airlines | 1 | 3 | 1 |
| Weekly flights | 14 | – | – |
| Flight time | 2h 35m | 1h 59m | 2h 26m |
| Departure OTP | 100% | – | – |
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 14 weekly departures, this is a well 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 14 weekly flights outbound and 14 return, totaling 28 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Baltimore/Washington International Thurgood Marshall, LaGuardia and Chicago O'Hare. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Portsmouth (PSM), Rockland (RKD) and Manchester (MHT).