£113 Cheap Flights from Portland (PDX) to Chicago (ORD)

View £113 flight on Wed, 27 May 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 £113 for one-way flights and £259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Wed, 20 May - Wed, 27 May
PDX
Portland
ORD
Chicago
£259 Return, found 3 hours ago
£259
Return
found 3 hours ago
Select Alaska Airlines flight, departing Wed, 20 May from Portland to Chicago, returning Wed, 27 May, priced at £259 found 3 hours ago
Alaska Airlines
Wed, 20 May - Wed, 27 May
PDX
Portland
ORD
Chicago
£260 Return, found 3 hours ago
£260
Return
found 3 hours ago
Select Alaska Airlines flight, departing Wed, 20 May from Portland to Chicago, returning Wed, 27 May, priced at £260 found 3 hours ago
Alaska Airlines
Wed, 29 Jul - Tue, 4 Aug
PDX
Portland
ORD
Chicago
£266 Return, found 2 days ago
£266
Return
found 2 days ago
Select Alaska Airlines flight, departing Wed, 29 Jul from Portland to Chicago, returning Tue, 4 Aug, priced at £266 found 2 days ago
Alaska Airlines
Wed, 29 Jul - Tue, 4 Aug
PDX
Portland
ORD
Chicago
£266 Return, found 2 days ago
£266
Return
found 2 days ago
Select Alaska Airlines flight, departing Wed, 29 Jul from Portland to Chicago, returning Tue, 4 Aug, priced at £266 found 2 days ago
Alaska Airlines
Tue, 28 Jul - Mon, 3 Aug
PDX
Portland
ORD
Chicago
£274 Return, found 5 days ago
£274
Return
found 5 days ago
Select Alaska Airlines flight, departing Tue, 28 Jul from Portland to Chicago, returning Mon, 3 Aug, priced at £274 found 5 days ago
Alaska Airlines
Wed, 20 May - Wed, 27 May
PDX
Portland
ORD
Chicago
£293 Return, found 3 hours ago
£293
Return
found 3 hours ago
Select Alaska Airlines flight, departing Wed, 20 May from Portland to Chicago, returning Wed, 27 May, priced at £293 found 3 hours ago
Alaska Airlines
Wed, 20 May - Wed, 27 May
PDX
Portland
ORD
Chicago
£297 Return, found 3 hours ago
£297
Return
found 3 hours ago
Select Alaska Airlines flight, departing Wed, 20 May from Portland to Chicago, returning Wed, 27 May, priced at £297 found 3 hours ago
Alaska Airlines
Sun, 17 May - Sun, 24 May
PDX
Portland
ORD
Chicago
£300 Return, found 3 hours ago
£300
Return
found 3 hours ago
Select Alaska Airlines flight, departing Sun, 17 May from Portland to Chicago, returning Sun, 24 May, priced at £300 found 3 hours ago
Alaska Airlines
Sun, 17 May - Sun, 24 May
PDX
Portland
ORD
Chicago
£304 Return, found 3 hours ago
£304
Return
found 3 hours ago
Select Alaska Airlines flight, departing Sun, 17 May from Portland to Chicago, returning Sun, 24 May, priced at £304 found 3 hours ago
Alaska Airlines
Wed, 29 Jul - Tue, 4 Aug
PDX
Portland
ORD
Chicago
£311 Return, found 2 days ago
£311
Return
found 2 days ago
Select Alaska Airlines flight, departing Wed, 29 Jul from Portland to Chicago, returning Tue, 4 Aug, priced at £311 found 2 days ago

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

May is typically the cheapest month to fly

From £152 - £218 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 £259. 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.

Frequently asked questions

What is the cheapest month to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is typically the cheapest month to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.), with average return fares of approximately £213. This is about 19% lower than the average price throughout the year. September often sees lower prices as the summer travel rush ends and before the holiday season begins, leading to reduced demand. Other cheap months to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) include February and August.
Which airlines fly direct from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter PDX to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best airline to fly with from Portland, OR (PDX-Portland Intl.) (PDX) to Chicago, IL (ORD-O'Hare Intl.) (ORD) will differ from traveller to traveller. If you like to fly early, AS offers early morning flights. If price is the most important factor, UA typically offers the lowest fares. AS offers the most daily flights from Portland, OR (PDX-Portland Intl.) (PDX) to Chicago, IL (ORD-O'Hare Intl.) (ORD), which is brilliant if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The best time to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) is typically September. This month offers a great balance, as it's one of the cheapest times to fly with average return fares around £213, and it's also a popular month for travel, meaning you'll have plenty of flight options to choose from. This information is based on booking data from the past year.
How many flights per day from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 10 nonstop flights per day from Portland International (PDX) to O'Hare International (ORD). For even more choice, look at flights that include layovers, as there are around 84 connecting flights per day. Some common connection points include Seattle - Tacoma International (SEA), San Francisco International (SFO), and Denver International (DEN).
What is the earliest flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs at approximately 12:05 AM local time, operated by AA. This is a seasonal service active in June and July. An early departure like this can help maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll typically find the most flights from Portland International Airport (PDX) to O'Hare International Airport (ORD) on a Friday, with around 67 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include Alaska Airlines, United Airlines, and Delta Air Lines. Fridays also offer notably more flight options compared to other days of the week.
What are the most popular departure times for flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Portland Intl. (PDX) to O'Hare Intl. (ORD) are in the early morning, from 6am to 9am. About 29% of passengers prefer this time window. Many major carriers, including Alaska Airlines, United Airlines and American Airlines, offer flights during this window. This timing works well because it allows you to get an early start on your travel day, arriving in Chicago with plenty of time for business or leisure activities.
How long does it take to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Direct flights from PDX to ORD usually take about 4 hours, traveling roughly 1,734 miles. If you opt for a connecting flight, expect to add around 4 hours to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Select the "Business class" and "First class" filters when looking for PDX to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Portland Intl. (PDX)?
From Portland Intl. (PDX), you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Sky Harbor Intl. (PHX), McCarran Intl. (LAS), San Francisco Intl. (SFO) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Portland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines
Return price
£259
Distance
2774 km
Average flight time
6 hours 4 mins

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