Cheap Flights from Portland (PDX) to Chicago (ORD)

View AU$151 flight on Sat, 27 Sept 2025Opens in a new window

Popular airlines from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)

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Cheap Flights from Portland (PDX) to Chicago (ORD)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$301 Return, found 5 days ago
AU$301
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$301 found 5 days ago
American Airlines
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$302 Return, found 5 days ago
AU$302
Return
found 5 days ago
Select American Airlines flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$302 found 5 days ago
Alaska Airlines
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$316 Return, found 5 days ago
AU$316
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$316 found 5 days ago
Alaska Airlines
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$317 Return, found 5 days ago
AU$317
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$317 found 5 days ago
American Airlines
Sat, 6 Dec - Thu, 11 Dec
PDX
Portland
ORD
Chicago
AU$318 Return, found 1 day ago
AU$318
Return
found 1 day ago
Select American Airlines flight, departing Sat, 6 Dec from Portland to Chicago, returning Thu, 11 Dec, priced at AU$318 found 1 day ago
Delta
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$332 Return, found 5 days ago
AU$332
Return
found 5 days ago
Select Delta flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$332 found 5 days ago
American Airlines
Sat, 25 Oct - Fri, 31 Oct
PDX
Portland
ORD
Chicago
AU$335 Return, found 6 days ago
AU$335
Return
found 6 days ago
Select American Airlines flight, departing Sat, 25 Oct from Portland to Chicago, returning Fri, 31 Oct, priced at AU$335 found 6 days ago
Alaska Airlines
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$347 Return, found 5 days ago
AU$347
Return
found 5 days ago
Select Alaska Airlines flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$347 found 5 days ago
Alaska Airlines
Sat, 25 Oct - Fri, 31 Oct
PDX
Portland
ORD
Chicago
AU$349 Return, found 6 days ago
AU$349
Return
found 6 days ago
Select Alaska Airlines flight, departing Sat, 25 Oct from Portland to Chicago, returning Fri, 31 Oct, priced at AU$349 found 6 days ago
United
Sat, 27 Sept - Sat, 4 Oct
PDX
Portland
ORD
Chicago
AU$386 Return, found 5 days ago
AU$386
Return
found 5 days ago
Select United flight, departing Sat, 27 Sept from Portland to Chicago, returning Sat, 4 Oct, priced at AU$386 found 5 days ago

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

August is typically the cheapest month to fly

From AU$160 - AU$306 per traveller.
Flight from Portland to Chicago route information
Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Return price
AU$301
Distance
2774 km
Average flight time
6 hours 9 mins

Your quick guide to flights from Portland to Chicago

Pick up great flights from Portland to Chicago

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Portland to Chicago. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Portland to Chicago that take around hours.

Find cheap flights from Portland to Chicago

From the great flight deals with prices currently ranging from AU$301 to AU$386, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Portland to Chicago around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Chicago is normally in September.

Reasons to book your flight from Portland to Chicago with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Portland to Chicago across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Chicago right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Frequently asked questions

How much is a flight from PDX Airport to ORD?
Within the past 7 days on Expedia, for flights departing within the next year, the lowest price listed for a round-trip journey between PDX Airport and ORD was AU$301. Fares this cheap don't wait forever, so book yours today. 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 Airport to ORD?
Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from PDX to O'Hare Intl. Airport (ORD) 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 Portland Airport to ORD flights, you'll see a "no change fees" filter for you to select.
How far is the flight from PDX to O'Hare Intl. Airport (ORD)?
The flying distance from Portland Intl. Airport (PDX) to ORD is 2 800 kilometres. Sneak in a nap or make a start on the latest bestseller and the trip will whiz by.
Which airlines fly direct from Portland Airport to O'Hare Airport?
A popular airline that flies from Portland Airport to O'Hare Intl. Airport (ORD) is United Airlines (UA). It offers 86 flights a month. Another airline servicing this route is Alaska Airlines (AS). You'll have 30 flights every month to take your pick of.
Are Portland Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute?
It is possible to pick up a great last-minute deal from PDX Airport to O'Hare Intl. Airport (ORD), but it's also possible to miss out entirely! As many airlines publish prices up to 12 months in advance, it's worthwhile keeping an eye on fares early and being ready to pounce when you spot a bargain. Expedia compares air carrier prices and updates flight deals all the time, so you can rest easy knowing you're always getting the latest offers.

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