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Cheap Flights from Portland to Chicago $238.6

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Cheapest Flights from Portland to Chicago (PWM 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 (PWM to MDW)

Question : Should you take that vacation to Chicago in the next 30 days?
Answer : As of Mar 27th, the best day for booking to Chicago (MDW) is Mar 29th. It costs $260, which is 42% below the average price to book the same route.

Question : Is price more important than specific travel days for you?
Answer : For the month of April, Friday is your cheapest day to fly. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : How many days should you spend in Chicago?
Answer : The average time spent in Chicago by passengers from Portland is three days.

Question : What is the likelihood your flight will be delayed for this route?
Answer : Passengers on the Portland to Chicago 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 : What's the likelihood of you being delayed on this route?
Answer : Using the combined on-time percentage and average delay breakdown, Portland to Chicago currently has a 4 out of a possible 5 star rating. A 4-star rating means you should feel confident in getting to Chicago on time.

Question : Over the coming months, which airline is getting their passengers to Chicago Midway International Airport (MDW) round-trip the cheapest?
Answer : Delta Air Lines is offering the best deal at $260. Better take a look quickly because prices range all the way up to $687 over the next three months.

Question : What price range should you expect when booking from Portland (PWM) to Chicago (MDW)?
Answer : Ranging from $260 to $687, prices for PWM to MDW do change more than the majority of routes in the United States. Prices tend to be lower the further out you book.