Skip to main content
Beginning of main content

MDW (Chicago) to PDX (Portland) Flights $199.6

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap MDW to PDX Flights

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 PDX)

Question : How many days should you spend in Portland?
Answer : Passengers from MDW to PDX stay about one week on average.

Question : Over the coming months, which airline is getting their passengers to Portland International Airport (PDX) round-trip the cheapest?
Answer : Delta Air Lines is the leader in keeping costs down for their passengers over the next three months. Bookings are being made at just $254 and, when compared to the high-end bookings of $776, it's quite a deal.

Question : What is the fastest flight from MDW to PDX?
Answer : If you're able to take the quickest direct flight (which is offered by Southwest Airlines), you will be able to leave MDW at 8:50 AM CDT and get to PDX at 11:25 AM PDT (four hours and 35 minutes). Remember, there is a two-hour time difference.

Question : What is the cheapest day to fly in the next four weeks?
Answer : As of Jul 24th, the best day for booking to Portland (PDX) is Jul 28th. It costs $254, which is 51% below this route's average price.

Question : Is this route your best bet for getting to Portland with minimal delays?
Answer : MDW to PDX currently scores 2 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 2 stars, you should feel rather worried about getting to Portland on time.

Question : How long will the flight typically be from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)?
Answer : The average flight duration between MDW and PDX is four hours and 37 minutes.

Question : How often are flights late from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)?
Answer : Passengers are currently getting to their destination on schedule 73% of the time, which ranks in the 44th percentile worldwide. When a flight is late, it's a 24-minute delay on average.