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Cheap Flights from Chicago to Portland $252.45

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Cheapest Flights from Chicago to Portland (MDW to PDX)

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

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

Question : When traveling to Portland from Chicago, how long will you be in the air?
Answer : Flying from MDW to PDX typically takes about four hours and 37 minutes.

Question : How does Chicago to Portland stack up against the rest of the world in overall promptness?
Answer : MDW to PDX currently scores 3 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 3 stars, you should feel slightly worried about getting to Portland on time.

Question : Is there an alternative to Chicago Midway International Airport (MDW) for getting you to Portland?
Answer : Lucky for you, there is another airport near Chicago. O'Hare International Airport (ORD) is 16 miles away, and over the next few months, flights are being booked 48% cheaper than flights from Chicago Midway International Airport.

Question : How often are flights late from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)?
Answer : Flights from MDW to PDX are on time 76% of the time, ranking in the top 50% of the world. If a flight is delayed, though, expect an average of 23 minutes added to your flight time.

Question : What is the shortest flight from MDW to PDX?
Answer : Southwest Airlines can get you there in four hours and 35 minutes. So, if you were to leave Chicago at 8:50 AM CDT, you would arrive in Portland at 11:25 AM PDT (remember, there is a time change of two hours).

Question : What price range should you expect when booking from Chicago (MDW) to Portland (PDX)?
Answer : Ranging from $264 to $851, prices for MDW to PDX do fluctuate more than most routes in the United States. However, the sooner you book, the better price you tend to get.

Question : Who struggles with getting their passengers to Portland International Airport (PDX) on time?
Answer : If you're flying NetJets Aviation to Portland from Chicago, you may be tardy as they're late 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.