฿3,335 Cheap Flights from Portland (PDX) to Chicago (ORD)

View ฿3,335 flight on Wed, 7 May 2025Opens in a new window

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

Prices were available within the past 7 days and start at ฿3,335 for one-way flights and ฿6,665 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 7 May - Sat, 10 May
PDX
Portland
ORD
Chicago
฿6,665 Return, found 1 day ago
฿6,665
Return
found 1 day ago
Select Delta flight, departing Wed, 7 May from Portland to Chicago, returning Sat, 10 May, priced at ฿6,665 found 1 day ago
Delta
Wed, 7 May - Sat, 10 May
PDX
Portland
ORD
Chicago
฿7,510 Return, found 1 day ago
฿7,510
Return
found 1 day ago
Select Delta flight, departing Wed, 7 May from Portland to Chicago, returning Sat, 10 May, priced at ฿7,510 found 1 day ago
United
Wed, 7 May - Sat, 10 May
PDX
Portland
ORD
Chicago
฿7,855 Return, found 1 day ago
฿7,855
Return
found 1 day ago
Select United flight, departing Wed, 7 May from Portland to Chicago, returning Sat, 10 May, priced at ฿7,855 found 1 day ago
Delta
Tue, 2 Sep - Wed, 10 Sep
PDX
Portland
ORD
Chicago
฿8,350 Return, found 22 hours ago
฿8,350
Return
found 22 hours ago
Select Delta flight, departing Tue, 2 Sep from Portland to Chicago, returning Wed, 10 Sep, priced at ฿8,350 found 22 hours ago
Delta
Wed, 14 May - Sat, 17 May
PDX
Portland
ORD
Chicago
฿8,555 Return, found 1 day ago
฿8,555
Return
found 1 day ago
Select Delta flight, departing Wed, 14 May from Portland to Chicago, returning Sat, 17 May, priced at ฿8,555 found 1 day ago
Delta
Wed, 7 May - Sat, 10 May
PDX
Portland
ORD
Chicago
฿8,700 Return, found 1 day ago
฿8,700
Return
found 1 day ago
Select Delta flight, departing Wed, 7 May from Portland to Chicago, returning Sat, 10 May, priced at ฿8,700 found 1 day ago
Delta
Sat, 30 Aug - Thu, 11 Sep
PDX
Portland
ORD
Chicago
฿8,725 Return, found 22 hours ago
฿8,725
Return
found 22 hours ago
Select Delta flight, departing Sat, 30 Aug from Portland to Chicago, returning Thu, 11 Sep, priced at ฿8,725 found 22 hours ago
Delta
Wed, 7 May - Sat, 10 May
PDX
Portland
ORD
Chicago
฿8,900 Return, found 1 day ago
฿8,900
Return
found 1 day ago
Select Delta flight, departing Wed, 7 May from Portland to Chicago, returning Sat, 10 May, priced at ฿8,900 found 1 day ago
American Airlines
Wed, 7 May - Sat, 10 May
PDX
Portland
ORD
Chicago
฿9,035 Return, found 1 day ago
฿9,035
Return
found 1 day ago
Select American Airlines flight, departing Wed, 7 May from Portland to Chicago, returning Sat, 10 May, priced at ฿9,035 found 1 day ago
Hawaiian Airlines
Sat, 30 Aug - Sun, 7 Sep
PDX
Portland
ORD
Chicago
฿11,075 Return, found 22 hours ago
฿11,075
Return
found 22 hours ago
Select Hawaiian Airlines flight, departing Sat, 30 Aug from Portland to Chicago, returning Sun, 7 Sep, priced at ฿11,075 found 22 hours ago
Flight from Portland to Chicago route information
Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Hawaiian Airlines, United
Return price
฿6,665
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 ฿3,335 and roundtrip prices from ฿6,665. 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 ฿6,665. 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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