S$187 Cheap Flights from Portland to Chicago

View S$187 flight on Fri, 27 Mar, 2026Opens in a new window

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

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Cheap Flights from Portland to Chicago (PDX-ORD)

Prices were available within the past 7 days and start at S$187 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 (ORD)

August is typically the cheapest month to fly

From S$136 - S$348 per traveller.

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 . 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.

Travel information

Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Distance
2774 km
Average flight time
6 hours 7 mins

Book with confidence

Flights from Portland to Chicago

There are several airlines that operate frequent flights from Portland (PDX) to Chicago (ORD) including

The earliest flight leaves Portland Intl. Airport at 00:34 and arrives at O'Hare Intl. Airport at 04:59. The last flight of the day departs Portland at 23:59 and arrives at Chicago at 20:36.

The flight distance from Portland to Chicago is about 2806 km, the shortest flight is 03 hours 47 minutes with United Airlines.

Expedia lets you search across the largest number of airlines and Chicago flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Portland Chicago flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Portland to Chicago trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Portland to Chicago with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

Flights from Portland to Chicago

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