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 Airlines111111106:3013:20VIEW FLIGHTS

Flights from Portland International to Midway are very limited. Only Southwest Airlines operate flights, of which there is only 1 per week. The time of the departure for this flight is 06:30

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
06:30
AirlineFlight  No
Southwest AirlinesWN5919
VIEW FLIGHTS
Tuesday
06:50
AirlineFlight  No
Southwest AirlinesWN5919
VIEW FLIGHTS
Wednesday
06:50
AirlineFlight  No
Southwest AirlinesWN5919
VIEW FLIGHTS
Thursday
12:30
AirlineFlight  No
Southwest AirlinesWN5919
VIEW FLIGHTS
Friday
06:30
AirlineFlight  No
Southwest AirlinesWN5919
VIEW FLIGHTS
Saturday
06:45
AirlineFlight  No
Southwest AirlinesWN5919
VIEW FLIGHTS
Sunday
13:20
AirlineFlight  No
Southwest AirlinesWN5919
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
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 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.

Alternative Airports in United States with Connections from Portland International Airport

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