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Southwest Airlines flights from Portland to Chicago

Southwest Airlines flies Portland to Chicago nonstop 13 times a week, departures from 05:50 to 11:20, 3h 55m in the air.

Flights from Portland to Chicago

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Southwest Airlines on Portland to Chicago at a glance

flights a week
13
days of operation
Daily
first and last departure
05:50 - 11:20
flight time
3h 55m - 9h
aircraft
Boeing 737, Boeing 737-800
cheapest fare on the route
$145

Southwest Airlines Portland to Chicago 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
WN 2797
Southwest Airlines
05:55 Portland International
11:55 Chicago Midway International
4h
Seasonal
Boeing 737
WN 2523
Southwest Airlines
08:35 Portland International
14:35 Chicago Midway International
4h
Seasonal
Boeing 737
WN 2577
Southwest Airlines
06:10 Portland International
12:10 Chicago Midway International
4h
Seasonal
Boeing 737
WN 644
Southwest Airlines
05:15 Portland International
11:10 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 4957
Southwest Airlines
11:50 Portland International
17:45 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 644
Southwest Airlines
06:05 Portland International
12:00 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 644
Southwest Airlines
05:20 Portland International
11:15 Chicago Midway International
3h 55m
Seasonal
Boeing 737
WN 4957
Southwest Airlines
11:30 Portland International
17:25 Chicago Midway International
3h 55m
Seasonal
Boeing 737

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.

Other airlines flying Portland to Chicago

Nonstop flights by the current schedule

United Airlines Alaska Airlines American Airlines All flights Portland to Chicago

Frequently asked questions

How many Southwest Airlines flights are there from Portland to Chicago?
13 nonstop flights a week, 18 flight numbers in the schedule: Daily.
How long is the Southwest Airlines flight from Portland to Chicago?
From 3 hours 55 minutes to 9 hours nonstop, depending on the flight.
Which aircraft does Southwest Airlines fly from Portland to Chicago?
Boeing 737 and Boeing 737-800.