Southwest Airlines
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Midway International Airport
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United States
Portland International Airport
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Scan through all non-stop flights from Chicago to Portland. The full flight schedule below gives an overview of all non-stop flights from MDW to PDX, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
In Portland, the summers are known for being warm, long, and dry, with temperatures typically reaching about 30°C (86°F). The area’s breathtaking scenery complements the sun-filled lifestyle, making it a popular destination for visitors all year round who are looking for relaxation, fun by the water, and the beauty of the outdoors.
Portland is best explored from mid-spring to summer, specifically between April and September, as most rainfall occurs from October to February.
Currently, there is only one airline operating non-stop flights from Chicago MDW to Portland PDX, 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 MDW PDX flight schedule.
Flights from MDW to PDX are operated 14 times a week, with an average of 2 flights per day. Departure times vary between 09:40 - 22:30. The earliest flight departs at 09:40, the last flight departs at 22:30. 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 Chicago to Portland takes 4 hours and 10 minutes. The flight distance between Chicago and Portland is 1,745 miles (or 2,808 km).
There is 1 airport in Portland: Portland International Airport (PDX).
There are 14 flights per week flying from Chicago to Portland (as of April 2026).
4 hours and 10 minutes is the average flight time from Chicago to Portland.
The distance from Chicago to Portland is 1,745 miles (2,808 kilometers).
Southwest Airlines is the only airline flying nonstop from Chicago to Portland.
There are no alliances flying direct from Chicago to Portland at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Portland:
The earliest flight departs at 09:40 from Chicago and arrives at 12:10 at Portland.
The latest flight departs at 22:30 from Chicago and arrives at 00:55 at Portland.
1,745 miles (2,808 km) · 4h 10m
10:05
12:30
Southwest Airlines
WN 3975
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:05
12:25
Southwest Airlines
WN 1651
Southwest Airlines
Boeing 757
Y
W
J
F
10:10
12:30
Southwest Airlines
WN 3579
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:15
12:35
Southwest Airlines
WN 2497
Southwest Airlines
Boeing 757
Y
W
J
F
10:15
12:35
Southwest Airlines
WN 2497
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:30
12:50
Southwest Airlines
WN 3975
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:00
13:20
Southwest Airlines
WN 3975
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:05
20:25
Southwest Airlines
WN 3579
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
20:50
23:10
Southwest Airlines
WN 2497
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:40
00:05
Southwest Airlines
WN 3976
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:45
00:05
Southwest Airlines
WN 3579
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:50
00:10
Southwest Airlines
WN 3579
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
22:20
00:45
Southwest Airlines
WN 3976
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
22:30
00:55
Southwest Airlines
WN 3976
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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