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

We've found the cheapest flights to Chicago

Returns from £244.68

One-way from £115.14

Flights from Portland International to Midway are operated by 2 airliners including Delta Air Lines and Southwest Airlines. The official airport code for Portland International is PDX and for Midway it is MDW.

The cost of flights varies on the time and day you fly. If you know the dates you wish to travel then book you flights as soon as you can. The earlier you book your lights the cheaper they will be. You can get saving of up to 50% of you book 2 or 3 months in advance! If it is possible, you should book your flights 2 or more months in advance as ticket prices will be substantially lower.

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

Below you will see all the airlines that fly from Portland International (PDX) to Midway (MDW) and the number of flights they operate each day.

Flights Chart
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines333332205:1023:30VIEW FLIGHTS
Delta Air Lines010000011:0011:00VIEW 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 WN1148, WN130, WN3202 and WN3203 with times between 05:10 and 23:30.

If you would like to find out more information on availably, flight times or if you would like to book your flight, you can visit Southwest Airlines direct at www.southwest.com/?ref=southwestairlines.com.

The flight time for the selected route vary based on the month you will travel, but below we has summarised the most common times they will fly. We recommend you only take these times as guidance and check with appropriate airline for the exact times for the date you depart.

Flights Time In WeekDays
DayFlight TimesFlights
Monday
06:00
AirlineFlight  No
Southwest AirlinesWN1148
11:50
AirlineFlight  No
Southwest AirlinesWN3202
23:30
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS
Tuesday
06:00
AirlineFlight  No
Southwest AirlinesWN3669
11:00
AirlineFlight  No
Delta Air LinesDL8962
11:15
AirlineFlight  No
Southwest AirlinesWN3202
23:30
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS
Wednesday
06:00
AirlineFlight  No
Southwest AirlinesWN3669
11:15
AirlineFlight  No
Southwest AirlinesWN3202
23:30
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS
Thursday
06:00
AirlineFlight  No
Southwest AirlinesWN1148
11:50
AirlineFlight  No
Southwest AirlinesWN3202
23:30
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS
Friday
06:00
AirlineFlight  No
Southwest AirlinesWN1148
11:50
AirlineFlight  No
Southwest AirlinesWN3202
23:30
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS
Saturday
06:05
AirlineFlight  No
Southwest AirlinesWN3325
23:30
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS
Sunday
05:10
AirlineFlight  No
Southwest AirlinesWN130
05:20
AirlineFlight  No
Southwest AirlinesWN3203
VIEW FLIGHTS

Other routes are also possible. Flying from a different airport may offer more convenient flight times, so below we have we have put a list of other routes that may well be suitable.

Alternative Direct Routes
RouteStopsDistanceFlying Time
Seattle Boeing Field King County to Chicago Midway04 Hours 5 Minutes
Seattle to Chicago Midway04 Hours 5 Minutes
Salem Mcnary Field to Chicago Midway04 Hours 10 Minutes

Over the past 10 years flight regulations have become very strict so we advise you to leave plenty of time to check in and get through customs.

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

DIRECT Southwest Airlines
What is the cheapest direct flight one way from Portland PDX to Chicago MDW?
The cheapest direct flight one way from Portland PDX to Chicago MDW is £115.14 ($152 €133.41)
£115.14
$152 | €133.41
Check Latest Price
DIRECT Southwest Airlines
What is the cheapest direct return flight from Portland PDX to Chicago MDW?
The cheapest direct return flight from Portland PDX to Chicago MDW is £244.68 ($323 €283.50)
£244.68
$323 | €283.50
Check Latest Price
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 £106.05 ($140 €122.88)
£106.05
$140 | €122.88
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 PDX to MDW

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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): Delta Air Lines, 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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