$119 Cheap Flights from Portland (PDX) to Chicago (ORD)

View $119 flight on Mon, Aug 10, 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 $119 for one-way flights and $238 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Aug 10 - Thu, Aug 13
PDX
Portland
ORD
Chicago
$238 Roundtrip, found 14 hours ago
$238
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Portland to Chicago, returning Thu, Aug 13, priced at $238 found 14 hours ago
Frontier Airlines
Mon, Aug 3 - Thu, Aug 13
PDX
Portland
ORD
Chicago
$244 Roundtrip, found 6 hours ago
$244
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Aug 3 from Portland to Chicago, returning Thu, Aug 13, priced at $244 found 6 hours ago
Frontier Airlines
Thu, Jul 30 - Sun, Aug 2
PDX
Portland
ORD
Chicago
$250 Roundtrip, found 3 hours ago
$250
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jul 30 from Portland to Chicago, returning Sun, Aug 2, priced at $250 found 3 hours ago
Frontier Airlines
Mon, Aug 3 - Thu, Aug 13
PDX
Portland
ORD
Chicago
$254 Roundtrip, found 6 hours ago
$254
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Aug 3 from Portland to Chicago, returning Thu, Aug 13, priced at $254 found 6 hours ago
Frontier Airlines
Sun, Sep 27 - Mon, Sep 28
PDX
Portland
ORD
Chicago
$260 Roundtrip, just found
$260
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Sep 27 from Portland to Chicago, returning Mon, Sep 28, priced at $260 just found
Frontier Airlines
Thu, Sep 10 - Mon, Sep 14
PDX
Portland
ORD
Chicago
$264 Roundtrip, found 7 hours ago
$264
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Portland to Chicago, returning Mon, Sep 14, priced at $264 found 7 hours ago
American Airlines
Sat, Sep 5 - Sat, Sep 12
PDX
Portland
ORD
Chicago
$282 Roundtrip, found 8 hours ago
$282
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Sep 5 from Portland to Chicago, returning Sat, Sep 12, priced at $282 found 8 hours ago
Alaska Airlines
Wed, Aug 5 - Thu, Aug 13
PDX
Portland
ORD
Chicago
$282 Roundtrip, found 9 hours ago
$282
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Wed, Aug 5 from Portland to Chicago, returning Thu, Aug 13, priced at $282 found 9 hours ago
Delta
Tue, Aug 4 - Thu, Aug 13
PDX
Portland
ORD
Chicago
$287 Roundtrip, found 1 day ago
$287
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 4 from Portland to Chicago, returning Thu, Aug 13, priced at $287 found 1 day ago
United
Sun, Jun 14 - Fri, Jun 19
PDX
Portland
ORD
Chicago
$294 Roundtrip, found 15 hours ago
$294
Roundtrip
found 15 hours ago
Select United flight, departing Sun, Jun 14 from Portland to Chicago, returning Fri, Jun 19, priced at $294 found 15 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $516
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $516

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

May is typically the cheapest month to fly

From $201 - $287 per traveler.

Frequently asked questions

How much does a flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $119 and cheap return flights from $238 Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights typically cost between $127 and $766, and return flights often range between $256 and $2452. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
September is the cheapest month to fly from Portland (PDX) to Chicago (ORD), with average round-trip fares around $285. This price is about 19% lower than the average throughout the year, as September often has less travel activity after the summer peak. Other economical months for this route include February and August.*Averages based on flights available on Expedia in the last year.
Which airlines fly direct from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Choose from 2 airlines operating direct flights from PDX to ORD:

  • United operates around 42 direct flights from PDX to ORD every week
  • American Airlines operates around 20 direct flights from PDX to ORD every week

What is the cheapest airline that flies from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
American Airlines is one of the cheapest airlines offering nonstop flights from Portland Intl. (PDX) to O'Hare Intl. (ORD), with round-trip tickets starting from around $195. This direct flight option is ideal for travelers looking for a quick journey. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
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) to Chicago, IL (ORD) will differ from traveler to traveler. If you like to fly early, United offers early morning flights. If price is the most important factor, United typically offers the lowest fares. Alaska Airlines offers the most daily flights from PDX to ORD, which is great 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.)?
For flights from Portland (PDX) to Chicago (ORD), the best months to fly are August and September. You can find return flights for about $285 during these months, which are both affordable and popular. August offers summer vibes, while September brings milder weather, making your trip enjoyable.*Prices based on flights available on Expedia in the last year.
How many flights per day from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 9 nonstop flights per day from Portland Intl. (PDX) to O'Hare Intl. (ORD). For more options, look at flights that include layovers.
What is the earliest flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Portland (PDX) to Chicago (ORD) typically departs at 12:05 AM, operated by American Airlines. This seasonal service is active in June and July, giving you an early start to your travels in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
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 (PDX) to Chicago (ORD) are in the early morning, from 6am to 9am. About 27% of passengers prefer this time window. Many major carriers, including United, Alaska Airlines, and Delta Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago with a full day ahead of you.
How long does it take to fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying nonstop from PDX to ORD takes around 4 hours, with the route covering approximately 1,734 miles. Flights with a layover typically take 4 hours 30 minutes longer than direct options. 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.)?
Business class seats are offered on the PDX to ORD route with American Airlines.First class cabins are available on:

  • Delta Air Lines
  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Hawaiian Airlines

How much is a business class flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
A direct, return business class ticket from Portland International Airport (PDX) to O'Hare International Airport (ORD) typically costs between $1,159 - $1,676. A non-stop, one-way business class flight is usually around $631 - $1,001. Prices often fluctuate based on seasonality and how early you book. You may also be able to find a cheaper business class journey between Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) if you opt for a connecting flight.*Prices based on flights available on Expedia in the last year.
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)?
When traveling from Portland Intl. (PDX) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Denver Intl. (DEN), Harry Reid Intl. (LAS), Oakland Intl. (OAK) 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.) Chicago Vacation Packages 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, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Sun Country Airlines, United
Roundtrip price
$238
Distance
1734 mi
Average flight time
6 hours 8 mins

Book with confidence

Portland to Chicago Flights

The cheapest times to fly from Portland to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Chicago are during the month of August. You can find some of the cheapest flights from Portland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Chicago

Sunday is one of the best days to book for cheap flights from Portland to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $119 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Portland to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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