£61 Cheap Flights from Portland (PDX) to Chicago (ORD)

View £61 flight on Tue, 6 Jan 2026Opens 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 and start at £61 for one-way flights and £145 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Thu, 23 Oct - Wed, 29 Oct
PDX
Portland
ORD
Chicago
£145 Return, found 4 days ago
£145
Return
found 4 days ago
Select Alaska Airlines flight, departing Thu, 23 Oct from Portland to Chicago, returning Wed, 29 Oct, priced at £145 found 4 days ago
Alaska Airlines
Fri, 31 Oct - Sat, 8 Nov
PDX
Portland
ORD
Chicago
£155 Return, just found
£155
Return
just found
Select Alaska Airlines flight, departing Fri, 31 Oct from Portland to Chicago, returning Sat, 8 Nov, priced at £155 just found
Alaska Airlines
Thu, 16 Oct - Fri, 24 Oct
PDX
Portland
ORD
Chicago
£162 Return, found 5 days ago
£162
Return
found 5 days ago
Select Alaska Airlines flight, departing Thu, 16 Oct from Portland to Chicago, returning Fri, 24 Oct, priced at £162 found 5 days ago
Alaska Airlines
Fri, 31 Oct - Sat, 8 Nov
PDX
Portland
ORD
Chicago
£163 Return, just found
£163
Return
just found
Select Alaska Airlines flight, departing Fri, 31 Oct from Portland to Chicago, returning Sat, 8 Nov, priced at £163 just found
Alaska Airlines
Thu, 23 Oct - Wed, 29 Oct
PDX
Portland
ORD
Chicago
£165 Return, found 4 days ago
£165
Return
found 4 days ago
Select Alaska Airlines flight, departing Thu, 23 Oct from Portland to Chicago, returning Wed, 29 Oct, priced at £165 found 4 days ago
Alaska Airlines
Thu, 16 Oct - Fri, 24 Oct
PDX
Portland
ORD
Chicago
£169 Return, found 5 days ago
£169
Return
found 5 days ago
Select Alaska Airlines flight, departing Thu, 16 Oct from Portland to Chicago, returning Fri, 24 Oct, priced at £169 found 5 days ago
Alaska Airlines
Tue, 28 Oct - Tue, 4 Nov
PDX
Portland
ORD
Chicago
£170 Return, found 20 hours ago
£170
Return
found 20 hours ago
Select Alaska Airlines flight, departing Tue, 28 Oct from Portland to Chicago, returning Tue, 4 Nov, priced at £170 found 20 hours ago
Alaska Airlines
Fri, 12 Dec - Sun, 14 Dec
PDX
Portland
ORD
Chicago
£174 Return, found 2 days ago
£174
Return
found 2 days ago
Select Alaska Airlines flight, departing Fri, 12 Dec from Portland to Chicago, returning Sun, 14 Dec, priced at £174 found 2 days ago
Alaska Airlines
Fri, 3 Oct - Tue, 7 Oct
PDX
Portland
ORD
Chicago
£176 Return, found 5 days ago
£176
Return
found 5 days ago
Select Alaska Airlines flight, departing Fri, 3 Oct from Portland to Chicago, returning Tue, 7 Oct, priced at £176 found 5 days ago
Alaska Airlines
Tue, 28 Oct - Tue, 4 Nov
PDX
Portland
ORD
Chicago
£177 Return, found 20 hours ago
£177
Return
found 20 hours ago
Select Alaska Airlines flight, departing Tue, 28 Oct from Portland to Chicago, returning Tue, 4 Nov, priced at £177 found 20 hours ago

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

August is typically the cheapest month to fly

From £77 - £150 per traveller.
Flight from Portland to Chicago route information
Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines
Return price
£145
Distance
2774 km
Average flight time
6 hours 9 mins

Compare flights from Portland to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Portland to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Portland Intl. to O'Hare Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Portland Intl. (PDX) to O'Hare Intl. (ORD)

The easiest way to view the best deals on flights from Portland to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Portland Intl. to O'Hare Intl. start at just £145 and range up to £177.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Portland and Chicago
  • booking your flight during October, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Portland to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Portland Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

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 £145. 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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