Flights from Portland Airport PDX to Chicago Airport MDW

Southwest Airlines is the only airliner who offers flights between Portland International and Midway. The flight time is approximately 4 Hours 7 Minutes.

The exact cost of the flight we vary quite significantly base on the dates you travel, the time of day you will depart and how long in advance you pre book the flights. The cheapest flights available will generally be mid week or late in the evening, so if you are on a budget then these are the flight times you should consider. Alternatively, you could book well in advance and you flight could be up to 50% cheaper, especially with budget airliners. The ticket prices for most airliners will increase the closer you get the departure date, so as soon as you know the date you will travel you should book your flights.

The time zone at Midway is different from Portland International, so please be aware of this when making travel arrangements.

For a full summary of all the airliners that fly from Portland International to Midway, please see the table below.

Flights Chart
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines333332205:3020:55VIEW FLIGHTS

Most people choose to fly with Southwest Airlines. They offer the largest number of flights so they have times which are most likely to suite you. The flights they offer will go by the flight numbers WN1489, WN2426, WN2658 and WN2995 with times between 05:30 and 20:55.

If you would like more information on this flight the please visit the website for Southwest Airlines at www.southwest.com/?ref=southwestairlines.com. You will be able to find the latest availability, prices and make your booking online.

Flight times for the route are summarised in the table below. These time were correct at the time of writing, but please be aware that times may vary from time to time so please check their website for exact times and the dates you wish to fly.

Flights Time In WeekDays
DayFlight TimesFlights
Monday
12:00
AirlineFlight  No
Southwest AirlinesWN1489
13:45
AirlineFlight  No
Southwest AirlinesWN2658
15:00
AirlineFlight  No
Southwest AirlinesWN967
VIEW FLIGHTS
Tuesday
06:15
AirlineFlight  No
Southwest AirlinesWN835
16:35
AirlineFlight  No
Southwest AirlinesWN2995
20:55
AirlineFlight  No
Southwest AirlinesWN2426
VIEW FLIGHTS
Wednesday
12:15
AirlineFlight  No
Southwest AirlinesWN835
16:35
AirlineFlight  No
Southwest AirlinesWN2995
20:55
AirlineFlight  No
Southwest AirlinesWN2426
VIEW FLIGHTS
Thursday
06:00
AirlineFlight  No
Southwest AirlinesWN1489
15:00
AirlineFlight  No
Southwest AirlinesWN967
19:35
AirlineFlight  No
Southwest AirlinesWN2658
VIEW FLIGHTS
Friday
09:05
AirlineFlight  No
Southwest AirlinesWN967
12:00
AirlineFlight  No
Southwest AirlinesWN1489
19:35
AirlineFlight  No
Southwest AirlinesWN2658
VIEW FLIGHTS
Saturday
10:00
AirlineFlight  No
Southwest AirlinesWN2995
11:50
AirlineFlight  No
Southwest AirlinesWN2014
VIEW FLIGHTS
Sunday
05:30
AirlineFlight  No
Southwest AirlinesWN3981
13:35
AirlineFlight  No
Southwest AirlinesWN2426
VIEW FLIGHTS

If you are flexible on the airport you depart from, then there are other airports that offer direct flights to Midway. You can see full details of these below.

Alternative Direct Routes
RouteStopsDistanceFlying Time
Seattle Boeing Field King County to Chicago Midway04 Hours 5 Minutes
Hillsboro to Chicago Midway04 Hours 9 Minutes
Seattle to Chicago Midway04 Hours 5 Minutes

Please remember to leave plenty of time to get though customers when you are departing form the airports. Flights regulations are getting very strict these days so getting through customs can take in excess of 1 hour in some cases.

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Flight Price FAQ - Portland (PDX) to Chicago (MDW)

1+ STOP(S)
What is the cheapest flight one way from Portland PDX to Chicago MDW?
The cheapest flight one way from Portland PDX to Chicago MDW is £41.15 ($54 €49.17)
£41.15
$54 | €49.17
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1+ STOP(S)
What is the cheapest return flight from Portland PDX to Chicago MDW?
The cheapest return flight from Portland PDX to Chicago MDW is £82.31 ($108 €98.34)
£82.31
$108 | €98.34
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Flight Info FAQ - Portland (PDX) to Chicago (MDW)

Who flies from Portland to Chicago?
The following airlines fly from Portland (PDX) to Chicago (MDW): Southwest Airlines.
How far is the flight from Portland to Chicago?
The flight from Portland to Chicago is 2,811KM or 1,747 miles.
How long does the flight from Portland to Chicago to take?
The flight from Portland to Chicago takes 4 Hours 7 Minutes.

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