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

View AU$252 flight on Sun, 8 Nov 2026Opens in a new window

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

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

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 12 Sept - Thu, 17 Sept
ORD
Chicago
PDX
Portland
AU$505 Return, found 2 days ago
AU$505
Return
found 2 days ago
Select American Airlines flight, departing Sat, 12 Sept from Chicago to Portland, returning Thu, 17 Sept, priced at AU$505 found 2 days ago
American Airlines
Wed, 30 Sept - Wed, 7 Oct
ORD
Chicago
PDX
Portland
AU$507 Return, found 3 days ago
AU$507
Return
found 3 days ago
Select American Airlines flight, departing Wed, 30 Sept from Chicago to Portland, returning Wed, 7 Oct, priced at AU$507 found 3 days ago
American Airlines
Sat, 12 Sept - Thu, 17 Sept
ORD
Chicago
PDX
Portland
AU$519 Return, found 2 days ago
AU$519
Return
found 2 days ago
Select American Airlines flight, departing Sat, 12 Sept from Chicago to Portland, returning Thu, 17 Sept, priced at AU$519 found 2 days ago
American Airlines
Wed, 30 Sept - Wed, 7 Oct
ORD
Chicago
PDX
Portland
AU$521 Return, found 3 days ago
AU$521
Return
found 3 days ago
Select American Airlines flight, departing Wed, 30 Sept from Chicago to Portland, returning Wed, 7 Oct, priced at AU$521 found 3 days ago
American Airlines
Wed, 30 Sept - Wed, 7 Oct
ORD
Chicago
PDX
Portland
AU$529 Return, found 3 days ago
AU$529
Return
found 3 days ago
Select American Airlines flight, departing Wed, 30 Sept from Chicago to Portland, returning Wed, 7 Oct, priced at AU$529 found 3 days ago
Delta
Sat, 12 Sept - Thu, 17 Sept
ORD
Chicago
PDX
Portland
AU$532 Return, found 2 days ago
AU$532
Return
found 2 days ago
Select Delta flight, departing Sat, 12 Sept from Chicago to Portland, returning Thu, 17 Sept, priced at AU$532 found 2 days ago
American Airlines
Sat, 12 Sept - Thu, 17 Sept
ORD
Chicago
PDX
Portland
AU$533 Return, found 2 days ago
AU$533
Return
found 2 days ago
Select American Airlines flight, departing Sat, 12 Sept from Chicago to Portland, returning Thu, 17 Sept, priced at AU$533 found 2 days ago
American Airlines
Wed, 30 Sept - Wed, 7 Oct
ORD
Chicago
PDX
Portland
AU$543 Return, found 3 days ago
AU$543
Return
found 3 days ago
Select American Airlines flight, departing Wed, 30 Sept from Chicago to Portland, returning Wed, 7 Oct, priced at AU$543 found 3 days ago
Alaska Airlines
Wed, 9 Sept - Sat, 12 Sept
ORD
Chicago
PDX
Portland
AU$571 Return, found 5 days ago
AU$571
Return
found 5 days ago
Select Alaska Airlines flight, departing Wed, 9 Sept from Chicago to Portland, returning Sat, 12 Sept, priced at AU$571 found 5 days ago
United
Sat, 12 Sept - Thu, 17 Sept
ORD
Chicago
PDX
Portland
AU$646 Return, found 2 days ago
AU$646
Return
found 2 days ago
Select United flight, departing Sat, 12 Sept from Chicago to Portland, returning Thu, 17 Sept, priced at AU$646 found 2 days ago

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

September is typically the cheapest month to fly

From AU$323 - AU$426 per traveller.

Frequently asked questions

How much does a flight from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) cost?
You can find one-way and return flights from ORD to PDX with Expedia. 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 our cheapest fares first, and use the Price Tracking tool to receive alerts when ORD to PDX ticket fares go up or down.
What is the cheapest month to fly from Chicago, IL (ORD) to Portland, OR (PDX)?
The cheapest months to fly from Chicago, IL (ORD) to Portland, OR (PDX) are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
Two airlines offer direct flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.). Here are the carriers:
  • United operates 55 direct flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) every week.
  • American Airlines operates 24 direct flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) every week.
How do I find cheap flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
To find a cheap flight from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland 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 Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
The best airline to fly with from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) will differ from traveler to traveler. If you like to fly early, Alaska Airlines offers early morning flights. If price is the most important factor, United typically offers the lowest fares. United offers the most daily flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.), 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 Chicago, IL (ORD) to Portland, OR (PDX)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
You'll find approximately 11 nonstop flights per day from Chicago O'Hare International (ORD) to Portland International (PDX). For even more choices, look at flights that include layovers, as there are around 124 connecting flights per day. Some common connection points include Seattle - Tacoma International (SEA), Denver International (DEN), and Minneapolis - St. Paul International (MSP).
What is the earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
The earliest flight from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) typically departs around 12:00 AM local time. This flight is operated by American Airlines. This is a seasonal service active in December. An early departure like this can help you make the most of 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 Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
You'll generally find the most flights from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) on a Thursday, with around 75 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United, American Airlines, and Delta.
What are the most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
The most popular departure times for flights from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) are in the morning, from 6am to 9am. Many major carriers, including Alaska Airlines, American Airlines and Delta, offer flights during this window. Many travellers prefer these early morning flights as they allow you to arrive at your destination with plenty of time to start your day.
How long does it take to fly from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
A nonstop flight from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.) typically takes around 4 hours 30 minutes. This route covers a distance of approximately 2790 kilometres. If you opt for a one-stop flight, your travel time will be longer, usually around 8 hours 30 minutes, while flights with two or more stops can take about 10 hours 30 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic, so it's always a good idea to allow for some extra time when planning your trip.
Can you fly business or first class from Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
Yes, you can fly business class or first class between ORD and PDX. Airlines that offer business class service on this route include:
  • Frontier Airlines
  • Delta
First class cabins are available on:
  • Alaska Airlines
  • Delta
  • United
  • American Airlines
How do I earn miles on a Chicago, IL (ORD) to Portland, OR (PDX) flight with Expedia?
It's easy to earn miles on a Chicago, IL (ORD) to Portland, OR (PDX) 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 Portland, OR (PDX) from Chicago, IL (ORD)?
If you're planning to travel to Portland from O'Hare Intl. (ORD), you can fly directly into Portland Intl. (PDX). Some flights may connect through major hubs like Harry Reid International Airport (LAS), Denver Intl. (DEN), or Sky Harbor Intl. (PHX) before reaching Portland. 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 Chicago, IL (ORD) to Portland, OR (PDX) at the last minute?
Typically, booking a last minute flight from Chicago, IL (ORD) to Portland, OR (PDX) 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 Chicago, IL (ORD) to Portland, OR (PDX) flight and hotel package?
Securing a Chicago, IL (ORD) to Portland, OR (PDX) 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 Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland Intl.)?
If you booked your Chicago, IL (ORD-O'Hare Intl.) to Portland, OR (PDX-Portland 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
O'Hare Intl.
Destination airport
Portland Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Roundtrip price
AU$505
Distance
2774 km
Average flight time
2 hours 32 mins

Book with confidence

Your quick guide to flights from Chicago to Portland

Pick up great flights from Chicago to Portland

With Expedia, you have your pick of flights a day with 20 airlines covering flights from Chicago to Portland. Whether you’re on a business trip, a family holiday or a luxury break, just enter your travel dates, hit search then check out your choice of flights. Select from return, one way or multi-city flights, and use the advance search tool if you want a direct or refundable flight. You can narrow your search to show you just your preferred cabin class and airline, too. It’s all easy. You can book direct flights from Chicago to Portland that take around hours.

Find cheap flights from Chicago to Portland

From the great flight deals with prices currently ranging from AU$505 to AU$646, you can choose to see the cheapest flights first. Generally, you can book the cheapest flights from Chicago to Portland around 4 to 6 weeks in advance. If your travel dates are flexible, try to avoid weekends and peak seasons – when you are more likely to grab the lowest prices. Even last minute, there are some impressive deals. The cheapest time to fly to Portland is normally in September.

Reasons to book your flight from Chicago to Portland with Expedia

Expedia makes it easy to find, book, and travel, with everything you need all in one place. When you enter your travel details, find fantastic deals just for you on flight tickets from Chicago to Portland across all the main airline carriers, so you can save time, dollars, and hassle finding the perfect flight. If you think your plans could change, choose refundable flights so any changes won’t cost you more. Book your flight to Portland right now and, if you join Expedia Rewards, you earn points this time and every time you travel with Expedia.

Your quick guide to flights from Chicago to Portland

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*Available to Expedia members.