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Cheap Flights from Portland to Chicago $251.46

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Cheapest Flights from Portland to Chicago (PDX to MDW)

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

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

Question : Are you paying the cheapest or highest price for your ticket to Chicago?
Answer : Flight prices are fluctuating more for this route than most routes in the United States, as they're ranging from $264 to $1,023. However, the sooner you book, the better price you tend to get.

Question : What is the cheapest day to fly in the next four weeks?
Answer : As of Mar 27th, the best day for deals to Chicago (MDW) is Apr 22nd. It costs $264, which is 50% below the average price to book the same route.

Question : Which airline is struggling to get to Chicago on time?
Answer : If you're flying NetJets Aviation to Chicago from Portland, you may be tardy as they're delayed 100% of the time. If you’re on NetJets Aviation, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Question : How many departure times are there on a given day?
Answer : The number of flight times varies by day, but on average, PDX to MDW sees two different options. That is lower than the national average of five.

Question : If traveling from PDX to MDW, how long can you expect to be in the air?
Answer : Flying from PDX to MDW typically takes about three hours and 53 minutes.

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

Question : If speed is all that matters, how can you get from PDX to MDW as quickly as possible?
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).