Southwest Airlines
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Portland International Airport
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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 PDX 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 PDX 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 PDX MDW flight schedule.
Flights from PDX to MDW are operated 14 times a week, with an average of 2 flights per day. Departure times vary between 05:10 - 23:55. The earliest flight departs at 05:10, the last flight departs at 23:55. 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 3 hours and 55 minutes. The flight distance between Portland and Chicago is 1,745 miles (or 2,808 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 14 flights per week flying from Portland to Chicago (as of April 2026).
3 hours and 55 minutes is the average flight time from Portland to Chicago.
The distance from Portland to Chicago is 1,745 miles (2,808 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 05:10 from Portland and arrives at 11:05 at Chicago.
The latest flight departs at 23:55 from Portland and arrives at 05:45 at Chicago.
1,745 miles (2,808 km) · 3h 55m
05:10
11:05
Southwest Airlines
WN 1162
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:20
11:15
Southwest Airlines
WN 280
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:20
11:15
Southwest Airlines
WN 280
Southwest Airlines
Boeing 757
Y
W
J
F
05:20
11:15
Southwest Airlines
WN 1162
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
05:25
11:20
Southwest Airlines
WN 280
Southwest Airlines
Boeing 757
Y
W
J
F
05:40
11:35
Southwest Airlines
WN 1162
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:15
12:10
Southwest Airlines
WN 280
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:00
13:55
Southwest Airlines
WN 1162
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
23:55
05:45
Southwest Airlines
WN 4161
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
23:55
05:50
Southwest Airlines
WN 3708
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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