PDX to MDW (Portland to Chicago) Flights

Last Minute Flights from PDX to MDW

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

OriginDestinationTravel DatesFlights From*
PDXChicagoMarch 20 to March 23$697
*Prices include taxes and fees

Cheapest PDX to MDW Flights

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

OriginDestinationTravel DatesFlights From*
PDXChicagoMay 6 to May 9$207
PDXChicagoMay 9 to May 12$213
PDXChicagoApril 22 to April 28$291
PDXChicagoMarch 27 to March 30$509
*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

What airlines fly direct from PDX to Chicago Airport?
At the moment, no airlines fly straight from PDX to Chicago Airport. If you want to travel to Chicago, book a flight with one or more stops.
How many flights are there from PDX to MDW?
Around 9 per day. If you're in a big hurry to visit Chicago, see if you can get your hands on an epic last-minute deal from Portland, OR (PDX-Portland Intl.) to Chicago, IL (MDW-Midway Intl.) and then lock it in straight away!
How long does it take to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (MDW-Midway Intl.)?
Portland, OR (PDX-Portland Intl.) to Chicago, IL (MDW-Midway Intl.) takes about 5 hours and 56 minutes. That's an ideal amount of time to get stuck into a gripping TV series, get absorbed in a podcast or settle back and have a snooze.
What is the flight distance from Portland, OR (PDX-Portland Intl.) to Chicago, IL (MDW-Midway Intl.)?
At a distance of 1,750 miles (2,800 1), you'll be in your seat for a while during this medium-haul flight. Need more legroom? Pick an aisle seat. Otherwise, sit at the window and gaze out at the views between Portland and Chicago.
How many morning flights are there from PDX to MDW?
The PDX to MDW air corridor is well taken care of, with 39 morning flights available per week.

  • Buckle up and take off with Delta Air Lines (DL). It has 22 weekly flights that depart before midday. The first one leaves at 12:40AM.
  • Alternatively, pick up a ticket with Frontier Airlines (F9) and leave the runway as early as 12:49AM. This airline offers 16 morning flights each week between PDX and MDW.

How many afternoon flights are there from PDX to MDW?
Say nope to the dreaded crack-of-dawn check in and select one of the 29 weekly afternoon and evening flights from PDX to MDW. Afternoon and evening services listed by Delta Air Lines (DL) jet off from 12:56PM. Overall, this popular airline operates 18 weekly flights departing after midday.
What is the earliest departure time out of Portland to Chicago?
12:40AM is the first flight taking off from PDX, arriving at MDW at 6:07PM. Save precious minutes in the morning by having your bags zipped up and ready to be tossed into your rideshare.
What is the latest departure time out of Portland to Chicago?
The latest flight leaves the runway at PDX at 11:50PM and comes in at MDW at 1:00PM. You'll have ample time to get ready for this flight.
What is the average price from Portland to Chicago?
Round-trip tickets from PDX to MDW start from around $207. Book today and score a fantastic deal. 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 simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from PDX to MDW, 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 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.

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