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Cheap Flights from Portland to Chicago $256.6

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Cheapest Flights from Portland to Chicago (PWM to ORD)

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

Interesting Facts About Flights from Portland to Chicago (PWM to ORD)

Question : Who struggles with getting their passengers to O'Hare International Airport (ORD) on time?
Answer : If you decide to book your flight with SkyWest Airlines, keep an eye on your departure time. 100% of flights from Portland International Jetport (PWM) to O'Hare International Airport (ORD) are late.

Question : Is price more important than specific travel days for you?
Answer : Sunday is your lowest-cost day to fly in the month of May. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Question : If you’re booking PWM to ORD, how many different choices of departure times do you have?
Answer : Each day is different, but on average, you can expect to see only one available departure time. You won't have as many options on this route as most others departing the United States.

Question : What is the shortest flight from PWM to ORD?
Answer : United Airlines can get you there in three hours and four minutes. For example, if you were to leave Portland at 4:25 PM EDT, you would arrive in Chicago at 6:29 PM CDT (remember, there is a time change of one hour).

Question : Which airline has been on time to O'Hare International Airport (ORD) from Portland International Jetport (PWM) the most?
Answer : The current leader is NetJets Aviation with a 100% on-time rate. Life has too much to offer to spend it waiting in an airport, so check out NetJets Aviation to get in and out of airports as quickly as possible. Perfection is hard to come by, so hopefully it continues.

Question : How often are flights late from Portland International Jetport (PWM) to O'Hare International Airport (ORD)?
Answer : This particular route gets passengers to O'Hare International Airport on time 75% of the time, which puts it in the bottom 50% of the world. When there is a delay, it averages 40 minutes.

Question : Should you take that vacation to Chicago in the next 30 days?
Answer : Since low prices are preferred, look at May 5th. As of Apr 17th, it's showing the cheapest ticket sales at $199. That is 40% below the average price for this route, so you can spend that extra money on a fun experience in Chicago.