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Cheap Flights from Chicago to Portland $249.35

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Cheapest Flights from Chicago to Portland (MDW to PWM)

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 PWM)

Question : Looking for the cheapest flight over the next 30 days?
Answer : As of Mar 27th, the best day for deals to Portland (PWM) is Apr 8th. It costs $260, which is 37% below the average price to book the same route.

Question : Over the coming months, which airline is getting their passengers to Portland International Jetport (PWM) round-trip the cheapest?
Answer : Delta Air Lines is the leader in keeping costs down for their passengers over the next three months. Fares are being booked at just $260, which is quite a deal when compared to the more expensive bookings of $675.

Question : What is the likelihood your flight will be delayed for this route?
Answer : Passengers on the Chicago to Portland route have been getting to their destination on time an incredible 100% of the time. When there is a delay, it averages less than 15 minutes.

Question : Is there another way to get to Portland International Jetport (PWM) besides Chicago Midway International Airport (MDW)?
Answer : Lucky for you, there is another airport near Chicago. O'Hare International Airport (ORD) is 16 miles away, and over the upcoming two months, flights are being booked 19% cheaper than flights from Chicago Midway International Airport.

Question : How does Chicago to Portland stack up against the rest of the world in overall promptness?
Answer : MDW to PWM currently scores 4 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 4 stars, you should feel confident in getting to Portland on time.

Question : Which airline has been the most dependable in getting passengers to their destination on time?
Answer : The current leader is Southwest Airlines with a 100% on-time rate. Don't spend more time waiting in an airport than you have to and stick with Southwest Airlines on this route. Perfection is hard to come by, so hopefully it continues.

Question : Will you do what it takes to get the absolute lowest-cost flight?
Answer : For the month of April, the cheapest day to fly is Saturday. Being flexible with your travel days garners even more savings during booking.