Flights from Chicago Airport (MDW) to Portland International Airport Airport (PDX)

We've found the cheapest flights to Portland

Returns from £238.80

One-way from £84.81

As flights from Midway to Portland International are in low demand, many airliners do not offer a direct flight. There is in fact only one airliner who you can fly with which is Southwest Airlines. The flight time is approximately 4 Hours 7 Minutes.

The most expensive flight prices are typically at weekends and daytime 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. We advise all our viewers to book well in advance. This way you will get the low priced tickets available.

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

The table below displays the numbers of daily flights from Midway (MDW) to Portland International (PDX) and the relevant airlines that fly.

Flights Chart
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines333333207:5022:25VIEW 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 WN1656, WN2121, WN3698 and WN3874 with times between 07:50 and 22:25.

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
09:10
AirlineFlight  No
Southwest AirlinesWN3874
15:55
AirlineFlight  No
Southwest AirlinesWN3698
22:05
AirlineFlight  No
Southwest AirlinesWN1656
VIEW FLIGHTS
Tuesday
07:50
AirlineFlight  No
Southwest AirlinesWN2121
16:05
AirlineFlight  No
Southwest AirlinesWN1656
21:30
AirlineFlight  No
Southwest AirlinesWN3874
VIEW FLIGHTS
Wednesday
07:50
AirlineFlight  No
Southwest AirlinesWN2121
16:05
AirlineFlight  No
Southwest AirlinesWN1656
21:30
AirlineFlight  No
Southwest AirlinesWN3874
VIEW FLIGHTS
Thursday
09:10
AirlineFlight  No
Southwest AirlinesWN3874
15:55
AirlineFlight  No
Southwest AirlinesWN3698
22:05
AirlineFlight  No
Southwest AirlinesWN1656
VIEW FLIGHTS
Friday
09:10
AirlineFlight  No
Southwest AirlinesWN3874
15:55
AirlineFlight  No
Southwest AirlinesWN3698
22:05
AirlineFlight  No
Southwest AirlinesWN1656
VIEW FLIGHTS
Saturday
07:45
AirlineFlight  No
Southwest AirlinesWN2121
16:00
AirlineFlight  No
Southwest AirlinesWN3698
21:10
AirlineFlight  No
Southwest AirlinesWN1656
VIEW FLIGHTS
Sunday
08:15
AirlineFlight  No
Southwest AirlinesWN2121
22:25
AirlineFlight  No
Southwest AirlinesWN1656
VIEW FLIGHTS

Instead of flying from Midway you could consider a few airports that are close by. Please see that table below of alternative routes.

Alternative Direct Routes
RouteStopsDistanceFlying Time
Appleton to Portland 03 Hours 57 Minutes
Grand Rapids Gerald R Ford to Portland 04 Hours 16 Minutes
Madison Dane County Regional to Portland 03 Hours 55 Minutes
Chicago O'Hare to Portland 04 Hours 6 Minutes

Before you book your flights make sure you your passport is valid and preferably has at least 6 months or more left before it expires. To renew your passport it can take several weeks to renew and with many airliners flights are not refundable.

Don't forget to book a rental car!

Find the cheapest hire vehicles in Portland Oregon, United States

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

DIRECT Southwest Airlines
What is the cheapest direct flight one way from Chicago MDW to Portland PDX?
The cheapest direct flight one way from Chicago MDW to Portland PDX is £84.81 ($114 €99.18)
£84.81
$114 | €99.18
Check Latest Price
DIRECT Southwest Airlines
What is the cheapest direct return flight from Chicago MDW to Portland PDX?
The cheapest direct return flight from Chicago MDW to Portland PDX is £238.80 ($321 €279.28)
£238.80
$321 | €279.28
Check Latest Price
1+ STOP(S)
What is the cheapest flight one way from Chicago MDW to Portland PDX?
The cheapest flight one way from Chicago MDW to Portland PDX is £67.70 ($91 €79.17)
£67.70
$91 | €79.17
Check Latest Price
1+ STOP(S)
What is the cheapest return flight from Chicago MDW to Portland PDX?
The cheapest return flight from Chicago MDW to Portland PDX is £135.39 ($182 €158.34)
£135.39
$182 | €158.34
Check Latest Price
Important Note: Prices shown are taken from searches performed for flights operating during the current month. Please use the "Latest Price" buttons to get the most up to date airfares.

Compare Flight Prices from MDW to PDX

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

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

Other Airports Connecting To Portland International Airport in united states

Don't forget to book a hire car!

Search for the cheapest rental car at Portland International Airport

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