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Cheap Flights from Portland to Chicago $186.82

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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 : Which airline is offering the cheapest round-trip flight from PWM to ORD?
Answer : JetBlue Airways has been booking passengers at the cheapest fare for flights scheduled throughout the next three months.

Question : Which airline is least likely to get you to ORD on time?
Answer : If you decide to book your flight with SkyWest Airlines, keep an eye on your departure time. Over the past month, SkyWest Airlines flights from Portland International Jetport (PWM) to O'Hare International Airport (ORD) are delayed 100% of the time.

Question : Which airline has been on time to O'Hare International Airport (ORD) from Portland International Jetport (PWM) the most?
Answer : NetJets Aviation leads the way with a 100% on-time rate. Stick to NetJets Aviation and you won't spend more time in airports than you have to. Perfection is hard to come by, so hopefully it continues.

Question : Looking for the cheapest flight over the next 30 days?
Answer : February 11th offers bookings (as of January 16th) that are 21% below the average price for this route. Saving on flight fares means you'll have more money to spend on your trip.

Question : How long do most people stay in Chicago when they fly in from Portland?
Answer : Of course you're not most people, but if you were, you'd stay roughly five days.

Question : Will you do what it takes to get the absolute lowest-cost flight?
Answer : In February, Wednesday is your cheapest day to fly. Flexibility is paramount when booking travel plans in order to keep costs down.