PDX to MDW (Portland to Chicago) Flights

Last Minute Flights from PDX to MDW

Best airfare and ticket deals for PDX to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
PDXChicagoApril 27 to May 4$218
*Prices include taxes and fees

Cheapest PDX to MDW Flights

Best airfare and ticket deals for PDX to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
PDXChicagoMay 18 to May 20$133
PDXChicagoMay 18 to May 21$138
PDXChicagoMay 17 to May 21$148
PDXChicagoOctober 18 to November 2$227
*Prices include taxes and fees
PDX to MDW Flight Details
Origin airport
Portland Intl.
Origin airport IATA code
PDX
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
1746 mi

Frequently asked questions

Which airlines with flights from PDX Airport to Chicago Airport allow free cancellation due to COVID-19?
To find all the airlines that offer flexible COVID-19 related changes, simply use our handy filter function. Start by typing in your dates. Then, once all the available flights appear, check the “No change fee” box under the “Flexible change policies” subheading on the left. Read through the carrier’s cancellation policies before reserving your PDX to MDW fare.
What airlines fly direct from PDX Airport to Chicago, IL Airport (MDW-Midway Intl.)?
Southwest Airlines (WN) does. Jump on one of the 43 flights per month that leave from PDX Airport and enjoy a straight run to MDW. Avoiding a tiresome stopover is the ideal way to kick off your Chicago adventure.
How many flights are there from PDX to MDW?
No less than 23 services operate every day between Portland, OR Airport (PDX-Portland Intl.) and Chicago, IL Airport (MDW-Midway Intl.). Buckle up because your plane to Chicago is ready to depart.
How long does it take to fly from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
This flight from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (MDW-Midway Intl.) will take some 5 hours and 40 minutes. Use the time to read the novel that’s been gathering dust beside your bed for months or simply get some sleep.
What is the flight distance from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (MDW-Midway Intl.)?
Covering a distance of 1750 miles (2800 km), you’ll be flying for some time during this medium-haul flight. Need leg space? Reserve an aisle seat. Otherwise, sidle up to a window and peer down at the landscapes between Portland and Chicago.
How many morning flights are there from PDX to MDW?
Those who prefer to rise early can decide between 83 morning flights from PDX to MDW each week.
  • You can fly off as early as 5:30AM if you choose to travel with Southwest Airlines (WN). This carrier offers 62 weekly services that depart in the morning.
  • Delta (DL) is another good option. It lists 21 morning flights weekly, with the earliest departure being 12:20AM.
How many afternoon flights are there from PDX to MDW?
Every week, you can choose between 84 afternoon and evening flights from PDX to MDW.
  • Southwest Airlines (WN) operates 57 flights each week departing after midday. The earliest is scheduled for 12:10PM.
  • Many travelers also fly with Delta (DL). You can hop on one of its 22 weekly afternoon and evening flights that fly to MDW from 12:19PM.
What is the earliest departure time out of Portland to Chicago?
12:20AM is the first flight from PDX, arriving at MDW at 5:07PM. Save time in the morning by having your bags zipped up and ready to be tossed in the boot.
What is the latest departure time out of Portland to Chicago?
Reserve a seat on the 10:38PM flight from PDX, arriving at MDW at 10:50AM, and give yourself time to finish up any last-minute vacation preparations. This is the latest flight you can get on this route.
What is the average price from Portland to Chicago?
You can find a return airfare from PDX to MDW beginning from around $133. The best fares sell out quickly, so book as soon as you know your travel dates. 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.

Portland to Chicago Flights

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

We present you with some of the hottest deals on airfare so stop that Google flights search. We want you to spend less on your flight from Portland to Chicago, 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.