MDW to PDX (Chicago to Portland) Flights

Last Minute Flights from MDW to PDX

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWPortlandMay 2 to May 5$268
*Prices include taxes and fees

Cheapest MDW to PDX Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
MDWPortlandMay 5 to May 24$198
MDWPortlandMay 24 to May 30$199
MDWPortlandMay 24 to July 26$213
MDWPortlandMay 24 to May 31$218
*Prices include taxes and fees
MDW to PDX Flight Details
Origin airport
Midway Intl.
Origin airport IATA code
MDW
Destination airport
Portland Intl.
Destination airport IATA code
PDX
Distance
1746 mi

Frequently asked questions

What airlines fly direct from MDW to PDX Airport?
To journey from Midway Airport to Portland Intl. Airport (PDX), you’ll have to book a flight with at least one stop in between. At the moment, there are no nonstop services on this particular route.
How many flights are there from MDW to PDX?
There are no less than 11 flights per day from Chicago, IL (MDW-Midway Intl.) to Portland, OR (PDX-Portland Intl.), so you have no shortage of ways to get to Portland. Just decide on a time and date that matches your plans and lock in your airfare.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Portland, OR (PDX-Portland Intl.)?
Roughly 6 hours and 39 minutes. Booked on a day flight? Grab a seat next to the window and enjoy the changing views. Alternatively, if you’re traveling from Chicago, IL (MDW-Midway Intl.) to Portland, OR (PDX-Portland Intl.) in the evening, close your eyes and touch down in Portland well rested.
What is the flight distance from Chicago, IL (MDW-Midway Intl.) to Portland, OR (PDX-Portland Intl.)?
At 1,750 miles (2,800 1), this medium-haul flight is no ultramarathon, but it’s no cakewalk either. Get to Portland feeling rested by enjoying a nap along the way.
How many morning flights are there from MDW to PDX?
Early risers can choose from 41 morning flights from MDW to PDX a week.

  • You can depart as early as 6:00AM if you travel with Delta Air Lines (DL). This airline lists 27 weekly flights that depart before midday.
  • Frontier Airlines (F9) offers 14 morning flights each week. The earliest time you can get up and away with this airline is 5:01AM.

How many afternoon flights are there from MDW to PDX?
With 38 weekly afternoon and evening flights from MDW to PDX, there’s no need to order that hotel wake-up call. Compare the offers from Delta Air Lines (DL) and select from 26 flights a week that leave after midday. The first departs at 12:00PM.
What is the earliest departure time out of Chicago to Portland?
5:01AM is the earliest scheduled flight out of MDW, landing at PDX at 7:05PM. Save valuable minutes in the morning by having your suitcase zipped up and ready to be tossed in the boot.
What is the latest departure time out of Chicago to Portland?
From MDW, the latest flight you can catch jets out at 10:59PM and comes in at PDX at 9:10AM. If you’re not a big fan of early starts, this is the flight to catch.
What is the average price from Chicago to Portland?
Flights from MDW to PDX start at around $198. You’ll want to move fast, because deals this good don’t hang around forever! This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Chicago to Portland Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from Chicago to Portland to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from MDW to PDX, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from Chicago to Portland, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.