￥18,230 Cheap Flights from Portland (PDX) to Chicago (MDW)

View ￥18,230 flight on Sat, Sep 27, 2025Opens in a new window

Popular airlines from Portland International Airport (PDX) to Chicago Midway Airport (MDW)

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Cheap Flights from Portland to Chicago (PDX-MDW)

Prices were available within the past 7 days and start at ￥18,230 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Portland (PDX) to Chicago (MDW)

September is typically the cheapest month to fly

From ￥17,433 - ￥62,599 per traveler.

Graph displaying average flight prices per month

Flights from Portland (PDX) to Chicago (MDW)
Origin airport
Portland Intl.
Destination airport
Midway Intl.
Distance
2794 km
Average flight time
5 hours 58 mins

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 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.

Frequently asked questions

How much is a flight from Portland Airport to MDW?
Start packing your suitcase, because round-trip flights from PDX to MDW start from . That's based on fares advertised within the last 7 days on Expedia for flights departing within the next year. Prices can move quickly, so book now to secure the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Portland Intl. Airport (PDX) to Chicago Airport?
This can vary from airline to airline, as each has its own set of terms and conditions. Visit the Customer Service Portal, where you'll find simple instructions on how to cancel your flight online.
How do I find cheap flights from PDX Airport to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for PDX Airport to MDW flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from PDX Airport to Midway Airport?
The average flight between Portland Intl. Airport (PDX) and Midway Airport is 5 hours and 56 minutes. If you're traveling with kids, it's always a good idea to pack a few healthy snacks in your carry-on baggage.
How far is the flight from PDX Airport to Midway Airport?
The flying distance between Portland Airport and Midway Intl. Airport (MDW) is 2,800 kilometers. Listen to your favorite tunes or make a start on the latest bestseller and the journey will fly by.
Which airlines fly direct from PDX to Midway Intl. Airport (MDW)?
At present, no airlines offer direct flights from Portland Airport to Midway Intl. Airport (MDW). You'll have to book a flight with at least one stop. To get the best price and connections, lock in your fare well ahead of time.
Are Portland Airport to MDW flight tickets cheaper when they're purchased at the last minute?
It is possible to nab amazing last-minute deals from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW), but it's also possible to miss out altogether! As many airlines advertise prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals regularly, so you can rest easy knowing you're always seeing the latest offers.

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