Southwest Airlines
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United States
Portland International Jetport
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United States
Midway International Airport
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Scan through all non-stop flights from Portland to Chicago. The full flight schedule below gives an overview of all non-stop flights from PWM to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Portland PWM to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their PWM MDW flight schedule.
Flights from PWM to MDW are operated 6 times a week, with an average of 1 flight per day. Departure times vary between 06:30 - 16:40. The earliest flight departs at 06:30, the last flight departs at 16:40. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Portland to Chicago takes 2 hours and 35 minutes. The flight distance between Portland and Chicago is 892 miles (or 1,436 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 6 flights per week flying from Portland to Chicago (as of April 2026).
2 hours and 35 minutes is the average flight time from Portland to Chicago.
The distance from Portland to Chicago is 892 miles (1,436 kilometers).
Southwest Airlines is the only airline flying nonstop from Portland to Chicago.
There are no alliances flying direct from Portland to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Portland to Chicago:
The earliest flight departs at 06:30 from Portland and arrives at 08:00 at Chicago.
The latest flight departs at 16:40 from Portland and arrives at 18:10 at Chicago.
892 miles (1,436 km) · 2h 35m
06:45
08:20
Southwest Airlines
WN 2464
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:30
09:05
Southwest Airlines
WN 3415
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
07:40
09:15
Southwest Airlines
WN 3415
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:55
17:40
Southwest Airlines
WN 3642
Southwest Airlines
Boeing 757
Y
W
J
F
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