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Cheap PDX to MDW Flights

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

Chicago

$169.58

Cheap PDX to MDW Flights

Question : How long do most people stay in Chicago?
Answer : Of course you're not most people, but if you were, you'd stay roughly one week.

Question : From Portland to Chicago, which day of the week is going to have the most flight times?
Answer : With six total flight time options, Saturday provides the most flexibility from PDX to MDW. The day with the fewest number of options is Sunday with three different times.

Question : If you’re booking PDX to MDW, how many different options of departure times do you have?
Answer : Depending on the day of the week, the number of flight times will change, but on average there are four. You won't have as many choices on this route as most other routes departing the United States.

Question : How often is the Portland International Airport (PDX) to Chicago Midway International Airport (MDW) route delayed?
Answer : Passengers are currently getting to their destination on schedule 84% of the time, which ranks in the top half of the world. When there is a delay, it averages less than half an hour.

Question : Is this route your best bet for getting to Chicago with minimal delays?
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 at ease about getting to Chicago on time.

Question : If speed is all that matters, how can you get from PDX to MDW as quickly as possible?
Answer : Southwest Airlines can get you there in three hours and 50 minutes. For example, if you were to leave Portland at 3:10 PM PST, you would arrive in Chicago at 9:00 PM CST (remember, there is a time change of two hours).

Question : What's the expected flight time for PDX to MDW?
Answer : On average, the flight time from PDX to MDW is three hours and 55 minutes.

Portland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Portland to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with PDX to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Portland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.