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PDX (Portland) to MDW (Chicago) Flights $263.6

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Cheap PDX to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.



Local Weather Chicago
June 84° 57°
July 85° 67°
August 83° 64°

Interesting Facts About Flights from Portland to Chicago (PDX to MDW)

Question : Best case scenario, how quickly can someone get from PDX to MDW?
Answer : Southwest Airlines can get you there in three hours and 50 minutes. For example, if you were to leave Portland at 3:10 PM PDT, you would arrive in Chicago at 9:00 PM CDT (remember, there is a two-hour time change).

Question : What are the chances this flight will be delayed?
Answer : This particular route gets passengers to Chicago Midway International Airport on time 84% of the time, which puts it in the top 50% of the world. When there is a delay, it averages less than 15 minutes.

Question : If your plans are flexible, have you considered changing your departure day?
Answer : The cheapest day to fly in July is Wednesday. Being flexible with your travel days garners even more savings during booking.

Question : Who's offering the cheapest round-trip flight to Chicago Midway International Airport (MDW) over the coming months?
Answer : Delta Air Lines is your best bet for finding that coveted low fare. They're offering fares as low as $297, while prices for other flights are as high as $835.

Question : Do travelers from Portland typically stay in Chicago for very long?
Answer : Passengers from PDX to MDW stay six days on average.

Question : How much should a trip from Portland (PDX) to Chicago (MDW) cost?
Answer : Flight prices are fluctuating less for this route than the majority of routes in the United States, as they're ranging from $297 to $835. Prices tend to be lower the further out you book.

Question : Which airline is struggling to get to Chicago on time?
Answer : If you decide to book your flight with NetJets Aviation, keep an eye on your departure time. 100% of flights from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) are late.