$81 Cheap Flights from Chicago (ORD) to Portland (PDX)

View $81 flight on Tue, Aug 19, 2025Opens in a new window

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

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Cheap Flights from Chicago to Portland (ORD-PDX)

Prices were available within the past 7 days and start at $81 for one-way flights and $162 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Aug 19 - Wed, Aug 20
ORD
Chicago
PDX
Portland
$162 Roundtrip, found 4 hours ago
$162
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Portland, returning Wed, Aug 20, priced at $162 found 4 hours ago
Spirit Airlines
Tue, Aug 12 - Wed, Aug 20
ORD
Chicago
PDX
Portland
$167 Roundtrip, found 5 hours ago
$167
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, Aug 12 from Chicago to Portland, returning Wed, Aug 20, priced at $167 found 5 hours ago
Spirit Airlines
Tue, Aug 19 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$171 Roundtrip, found 21 hours ago
$171
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Portland, returning Sun, Aug 31, priced at $171 found 21 hours ago
Spirit Airlines
Tue, Aug 12 - Sat, Aug 16
ORD
Chicago
PDX
Portland
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 12 from Chicago to Portland, returning Sat, Aug 16, priced at $174 found 1 hour ago
Spirit Airlines
Tue, Aug 12 - Thu, Aug 14
ORD
Chicago
PDX
Portland
$175 Roundtrip, found 2 hours ago
$175
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Aug 12 from Chicago to Portland, returning Thu, Aug 14, priced at $175 found 2 hours ago
Spirit Airlines
Tue, Aug 19 - Wed, Aug 20
ORD
Chicago
PDX
Portland
$176 Roundtrip, found 4 hours ago
$176
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Portland, returning Wed, Aug 20, priced at $176 found 4 hours ago
United
Sat, Aug 30 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$179 Roundtrip, found 4 hours ago
$179
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Aug 30 from Chicago to Portland, returning Sun, Aug 31, priced at $179 found 4 hours ago
Alaska Airlines
Wed, Aug 27 - Sat, Aug 30
ORD
Chicago
PDX
Portland
$191 Roundtrip, just found
$191
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, Aug 27 from Chicago to Portland, returning Sat, Aug 30, priced at $191 just found
Southwest Airlines
Sat, Aug 30 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$199 Roundtrip, found 4 hours ago
$199
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Chicago to Portland, returning Sun, Aug 31, priced at $199 found 4 hours ago
Delta
Tue, Oct 21 - Fri, Oct 31
ORD
Chicago
PDX
Portland
$223 Roundtrip, found 10 hours ago
$223
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Oct 21 from Chicago to Portland, returning Fri, Oct 31, priced at $223 found 10 hours ago

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

August is typically the cheapest month to fly

From $90 - $196 per traveler.

Graph displaying average flight prices per month

Alternative airports near Portland

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

Select flight to Portland Intl. PDX. Cheapest and Closest option available. Average driving time to city center is 17 minutes. Flights from $181
PDX
Portland Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $181
Flights from Chicago (ORD) to Portland (PDX)
Origin airport
O'Hare Intl.
Destination airport
Portland Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$162
Distance
1734 mi
Average flight time
2 hours 30 mins

Chicago to Portland Flights

The cheapest times to fly from Chicago to Portland

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 Chicago to Portland are during the month of August. You can find some of the cheapest flights from Chicago to Portland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Portland

Sunday is one of the best days to book for cheap flights from Chicago to Portland: 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 Chicago to Portland

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 Chicago to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $81 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 Chicago to Portland 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 Chicago to Portland 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.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX) cost?
You can book cheap return fares starting at $179 from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Alaska Airlines flight leaving ORD on August 16 2025 and touching down at PDX. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from ORD to PDX?
The cheapest flights from ORD to PDX are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
You can fly nonstop from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX) on a United Airlines flight.
What is the cheapest airline that flies from ORD to PDX?
Currently, the cheapest airline operating one-way flights from ORD to PDX is Alaska Airlines. You can take off on this route from $90. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on August 30 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
Each day, an average of 3 nonstop flights operate from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). Select the departure time that best fits your itinerary.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
More passengers fly between ORD and PDX at 4 PM than at any other point in the day. Rather skip the crowds? Pick a flight outside the busiest times and you could save on your ticket as well.
What day of the week has the most flights from ORD to PDX?
If you jet off on a Sunday, you'll get the widest range of choices for flights from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
The earliest flight jetting off from O'Hare Intl. Airport (ORD) is at around 8:56AM UTC-6. Board this plane and you'll arrive at Portland Intl. Airport (PDX) at approximately 11:39AM UTC-8. The overall travel time is 4h 43m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
The average flight duration from ORD to PDX is 4 hours and 42 minutes, covering a distance of 1,750 mi.
What airline has the least delays from ORD to PDX?
With 83% of journeys generally arriving as scheduled, United Airlines has the best on-time performance for nonstop flights from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). To monitor your flight status and get notified if anything changes, head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
To arrive at Portland Intl. Airport (PDX) without delays, pick a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Portland from O'Hare Intl. Airport (ORD)?
Portland Intl. Airport (PDX) is the only airport in Portland with direct flights from O'Hare Intl. Airport (ORD). Browse your options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX) last-minute?
Booking your plane ticket from ORD to PDX just before your getaway is typically more expensive. But if you're flexible with your schedule, you could land a cheap last-minute fare.
Is it cheaper to book an ORD to PDX flight and hotel package?
Booking an ORD to PDX flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Select from our impressive range of accommodations and then add activities, flights and car rentals to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
Typically, you can cancel or reschedule your ORD to PDX flight. However, additional charges may apply, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's fees and rules on flight changes, or if you'd like more details, visit our Customer Service portal.

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