€110 Cheap Flights Portland to Chicago (PDX-ORD)

View €110 flight on Sat, 28 Jun 2025Opens in a new window

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Cheap flights from Portland to Chicago (PDX-ORD)

Prices were available within the past 7 days and start at €110 for one-way flights and €169 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 12 Apr - Sat, 19 Apr
PDX
Portland
ORD
Chicago
€169 Return, found 23 hours ago
€169
Return
found 23 hours ago
Select American Airlines flight, departing Sat, 12 Apr from Portland to Chicago, returning Sat, 19 Apr, priced at €169 found 23 hours ago
Delta
Sat, 12 Apr - Sat, 19 Apr
PDX
Portland
ORD
Chicago
€188 Return, found 23 hours ago
€188
Return
found 23 hours ago
Select Delta flight, departing Sat, 12 Apr from Portland to Chicago, returning Sat, 19 Apr, priced at €188 found 23 hours ago
American Airlines
Sat, 12 Apr - Sat, 19 Apr
PDX
Portland
ORD
Chicago
€193 Return, found 23 hours ago
€193
Return
found 23 hours ago
Select American Airlines flight, departing Sat, 12 Apr from Portland to Chicago, returning Sat, 19 Apr, priced at €193 found 23 hours ago
American Airlines
Sat, 12 Apr - Sat, 19 Apr
PDX
Portland
ORD
Chicago
€202 Return, found 23 hours ago
€202
Return
found 23 hours ago
Select American Airlines flight, departing Sat, 12 Apr from Portland to Chicago, returning Sat, 19 Apr, priced at €202 found 23 hours ago
Delta
Sat, 12 Apr - Sat, 19 Apr
PDX
Portland
ORD
Chicago
€212 Return, found 23 hours ago
€212
Return
found 23 hours ago
Select Delta flight, departing Sat, 12 Apr from Portland to Chicago, returning Sat, 19 Apr, priced at €212 found 23 hours ago
American Airlines
Sat, 5 Apr - Sat, 12 Apr
PDX
Portland
ORD
Chicago
€218 Return, found 2 days ago
€218
Return
found 2 days ago
Select American Airlines flight, departing Sat, 5 Apr from Portland to Chicago, returning Sat, 12 Apr, priced at €218 found 2 days ago
American Airlines
Sat, 12 Apr - Sat, 19 Apr
PDX
Portland
ORD
Chicago
€227 Return, found 23 hours ago
€227
Return
found 23 hours ago
Select American Airlines flight, departing Sat, 12 Apr from Portland to Chicago, returning Sat, 19 Apr, priced at €227 found 23 hours ago
Delta
Sat, 5 Apr - Sat, 12 Apr
PDX
Portland
ORD
Chicago
€228 Return, found 2 days ago
€228
Return
found 2 days ago
Select Delta flight, departing Sat, 5 Apr from Portland to Chicago, returning Sat, 12 Apr, priced at €228 found 2 days ago
United
Sat, 5 Apr - Sat, 12 Apr
PDX
Portland
ORD
Chicago
€267 Return, found 2 days ago
€267
Return
found 2 days ago
Select United flight, departing Sat, 5 Apr from Portland to Chicago, returning Sat, 12 Apr, priced at €267 found 2 days ago
Hawaiian Airlines
Sat, 5 Apr - Sat, 12 Apr
PDX
Portland
ORD
Chicago
€281 Return, found 2 days ago
€281
Return
found 2 days ago
Select Hawaiian Airlines flight, departing Sat, 5 Apr from Portland to Chicago, returning Sat, 12 Apr, priced at €281 found 2 days ago
Portland to Chicago route information
Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Hawaiian Airlines, United
Return price
€169
Distance
2774 km

Perfect flights from Portland to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Portland to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of Chicago, surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Portland Intl. to O'Hare Intl. ticket options cater to your travel preferences, with incredible one-way fares from €110 and roundtrip prices from €169. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at O'Hare Intl. and explore Chicago and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your PDX to ORD travel arrangements today and embark on the journey of a lifetime in Chicago.

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 €169. 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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