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Direct flights from Portland International (PDX) to Chicago Midway International (MDW)

13 nonstop flights a week from Portland International (PDX) to Chicago Midway International (MDW) with 1 airline, 3h 55m to 9h in the air, 1,747 mi (2,811 km). Departures from 05:50 to 11:20.

Flights from Portland to Chicago

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Prices by day: Portland to Chicago

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Portland International (PDX) to Chicago Midway International (MDW) at a glance

flights a week
13
flights today
1
airline
1
flight time
3h 55m - 9h
distance
1,747 mi (2,811 km)
first and last departure
05:50 - 11:20

Portland International (PDX) to Chicago Midway International (MDW) flight schedule

13 flights a week. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 507
Southwest Airlines
05:50 Portland International
11:35 Chicago Midway International
4h 45m
Sat
Boeing 737
WN 507
Southwest Airlines
06:00 Portland International
11:50 Chicago Midway International
4h 50m
Mon, Tue, Wed, Thu
Boeing 737
WN 537
Southwest Airlines
07:35 Portland International
17:35 Chicago Midway International
9h
Mon, Thu, Fri, Sun
Boeing 737-800
WN 507
Southwest Airlines
08:30 Portland International
14:15 Chicago Midway International
4h 45m
Sat
Boeing 737-800
WN 696
Southwest Airlines
11:20 Portland International
17:05 Chicago Midway International
4h 45m
Mon, Tue, Wed, Thu
Boeing 737

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 507
Southwest Airlines
05:25 Portland International
11:15 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 507
Southwest Airlines
07:00 Portland International
12:45 Chicago Midway International
4h 45m
Seasonal
Boeing 737-800
WN 507
Southwest Airlines
05:45 Portland International
11:30 Chicago Midway International
4h 45m
Seasonal
Boeing 737
WN 507
Southwest Airlines
05:20 Portland International
11:05 Chicago Midway International
4h 45m
Seasonal
Boeing 737
WN 4309
Southwest Airlines
06:50 Portland International
12:40 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 3059
Southwest Airlines
10:50 Portland International
16:40 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 3059
Southwest Airlines
08:35 Portland International
14:25 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 4309
Southwest Airlines
06:10 Portland International
12:00 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 3059
Southwest Airlines
10:55 Portland International
16:45 Chicago Midway International
4h 50m
Seasonal
Boeing 737-800
WN 3216
Southwest Airlines
05:35 Portland International
11:25 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 2532
Southwest Airlines
12:15 Portland International
18:05 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 3216
Southwest Airlines
06:20 Portland International
12:10 Chicago Midway International
4h 50m
Seasonal
Boeing 737
WN 4559
Southwest Airlines
06:00 Portland International
11:55 Chicago Midway International
4h 55m
Seasonal
Boeing 737
WN 2901
Southwest Airlines
11:20 Portland International
17:15 Chicago Midway International
4h 55m
Seasonal
Boeing 737-800
WN 354
Southwest Airlines
06:00 Portland International
11:55 Chicago Midway International
4h 55m
Seasonal
Boeing 737
WN 4754
Southwest Airlines
05:35 Portland International
11:30 Chicago Midway International
3h 55m
Selected dates
Boeing 737
WN 2190
Southwest Airlines
05:40 Portland International
11:40 Chicago Midway International
4h
Seasonal
Boeing 737-800
WN 2523
Southwest Airlines
10:00 Portland International
15:55 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 2807
Southwest Airlines
05:55 Portland International
11:55 Chicago Midway International
4h
Seasonal
Boeing 737
WN 2523
Southwest Airlines
12:00 Portland International
17:55 Chicago Midway International
3h 55m
Seasonal

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 2 hours ahead of Portland.

Airlines flying Portland International (PDX) to Chicago Midway International (MDW)

Nonstop flights a week by the current schedule

Southwest Airlines13 a week

Frequently asked questions

How many nonstop flights are there from Portland International (PDX) to Chicago Midway International (MDW)?
13 nonstop flights a week by the current schedule, 18 flight numbers, 1 today.
How long is the flight from Portland International (PDX) to Chicago Midway International (MDW)?
From 3 hours 55 minutes to 9 hours nonstop, depending on the flight.
Which airlines fly nonstop from Portland International (PDX) to Chicago Midway International (MDW)?
Southwest Airlines (13 a week).
How far is Chicago Midway International (MDW) from Portland International (PDX)?
1,747 mi (2,811 km) in a straight line.
What are the earliest and latest flights from Portland International (PDX) to Chicago Midway International (MDW)?
The first departure is at 05:50 (Southwest Airlines), the last at 11:20 (Southwest Airlines), local time.