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Direct flights from Portland to Chicago

Airlines Schedules

PDX - MDW route map All flights from PDX to MDW non-stop. There are direct flights from Portland International (PDX), Oregon, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 13 weekly departures are currently scheduled on this route. Departure times range from 05:15 to 23:50 depending on the schedule period. The flight distance is 1756 miles (2825 km). Flight time ranges from 3 hours and 45 minutes to 4 hours.

PDX
Portland
USAPortland , USA
MDW
Chicago Midway
USAChicago , USA
PDX
Portland
USAPortland , USA
Chicago Midway
USAChicago , USA
MDW
Flight time 3h 45min to 4h 0min
Updated Oct 12, 2026
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Airlines with non-stop routes:

Southwest Airlines Low-cost carrier

Departure times vary between 05:15 and 23:50
S
M
T
W
T
F
S
Sun
Mon
Tue
Wed
Thu
Fri
Sat
13 flights/week
13 flights/week
Weekday-labels: HAS FLIGHTS UPCOMING NO FLIGHTS
View all flight dates
Flight schedule from Portland to Chicago with Southwest Airlines

This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.

 
Flight
Mon
Nov 9
Tue
Nov 10
Wed
Nov 11
Thu
Nov 12
Fri
Nov 13
Sat
Nov 14
Sun
Nov 15
WN507
----
06:00
06:00
----
----
08:30
----
WN3350
23:30
----
----
23:30
23:30
----
23:30

The timetable & schedule information was updated at 2026-10-12

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Portland to Chicago scheduled departures

Select a date to see every published non-stop departure between PDX and MDW.

Tuesday
Tue
Nov 10
1 flights(1)
Wednesday
Wed
Nov 11
1 flights(1)
Thursday
Thu
Nov 12
1 flights(1)
Friday
Fri
Nov 13
1 flights(1)
Saturday
Sat
Nov 14
1 flights(1)
Sunday
Sun
Nov 15
1 flights(1)
Monday
Mon
Nov 16
2 flights(2)
Time
Airline
Flight
06:00
Southwest Airlines Southwest Airlines
WN507
06:00
Southwest Airlines Southwest Airlines
WN507
23:30
Southwest Airlines Southwest Airlines
WN3350
23:30
Southwest Airlines Southwest Airlines
WN3350
08:30
Southwest Airlines Southwest Airlines
WN507
23:30
Southwest Airlines Southwest Airlines
WN3350
06:00
Southwest Airlines Southwest Airlines
WN507
11:20
Southwest Airlines Southwest Airlines
WN696
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PDX-MDW flight route
Route map from Portland, PDX to Chicago, MDW. The distance is 1756 miles or 2825 km.
Portland - Chicago direct flight map
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PDX - MDW route facts

  • Distance
    1756 miles (2825 km)
  • Flight time
    3 hours and 45 minutes to 4 hours
  • Airline
    Southwest Southwest
  • Airline alliances
    Low-cost carrier
  • Cabins
    Economy
  • Aircraft
    Boeing 737MAX 8 Passenger, Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737-700 Passenger (Scimitar Winglets)

Route FAQ

Southwest Airlines operates non-stop flights from PDX to MDW with 13 weekly departures.

Scheduled flight time from PDX to MDW ranges from 3 hours and 45 minutes to 4 hours. The route covers 1756 miles (2825 km).

13 weekly departures are currently scheduled on this route, with published departure times ranging from 05:15 to 23:50 depending on the schedule period.

Economy are currently scheduled on non-stop flights for this route.
Direct flights from Portland to IL, USA
From Portland to Chicago

ORD Chicago O Hare International
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