￥14,730 Cheap Flights from Portland (PDX) to Chicago (MDW)

View ￥14,730 flight on Wed, Dec 24, 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 ￥14,730 for one-way flights and ￥44,500 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥44,500 Roundtrip, found 2 days ago
￥44,500
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥44,500 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥47,730 Roundtrip, found 2 days ago
￥47,730
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥47,730 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥55,680 Roundtrip, found 2 days ago
￥55,680
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥55,680 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥57,940 Roundtrip, found 2 days ago
￥57,940
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥57,940 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥58,910 Roundtrip, found 2 days ago
￥58,910
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥58,910 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥60,950 Roundtrip, found 2 days ago
￥60,950
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥60,950 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥87,610 Roundtrip, found 2 days ago
￥87,610
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥87,610 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥93,090 Roundtrip, found 2 days ago
￥93,090
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥93,090 found 2 days ago
Delta
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥101,050 Roundtrip, found 2 days ago
￥101,050
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥101,050 found 2 days ago
United
Mon, Oct 27 - Sat, Nov 1
PDX
Portland
MDW
Chicago
￥161,380 Roundtrip, found 2 days ago
￥161,380
Roundtrip
found 2 days ago
Select United flight, departing Mon, Oct 27 from Portland to Chicago, returning Sat, Nov 1, priced at ￥161,380 found 2 days ago

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

October is typically the cheapest month to fly

From ￥17,380 - ￥66,005 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from ￥65,560
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from ￥65,560

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 ￥44,500. 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.

Travel information

Travel information

Origin airport
Portland Intl.
Destination airport
Midway Intl.
Roundtrip price
￥44,500
Distance
2794 km
Average flight time
6 hours 29 mins

Book with confidence

Book with confidence

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.

Portland to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Chicago nearby Airports

Chicago

Portland to O'Hare Intl.
￥30,490
*Available to Expedia members.