$65 Cheap Flights from Chicago (ORD) to Portland (PDX)

View $65 flight on Thu, Dec 4, 2025Opens in a new window

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

Today's featured flight deals from Chicago O'Hare Intl. Airport (ORD) to Portland International Airport (PDX)

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Chicago to Portland (ORD-PDX)

Prices were available within the past 7 days and start at $65 for one-way flights and $150 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at $150 just found
Frontier Airlines
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
$160 Roundtrip, just found
$160
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at $160 just found
Frontier Airlines
Thu, Dec 11 - Tue, Dec 16
ORD
Chicago
PDX
Portland
$174 Roundtrip, found 1 hour ago
$174
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Dec 11 from Chicago to Portland, returning Tue, Dec 16, priced at $174 found 1 hour ago
Frontier Airlines
Thu, Nov 13 - Sat, Nov 15
ORD
Chicago
PDX
Portland
$176 Roundtrip, found 8 hours ago
$176
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Chicago to Portland, returning Sat, Nov 15, priced at $176 found 8 hours ago
Frontier Airlines
Thu, Dec 4 - Wed, Dec 10
ORD
Chicago
PDX
Portland
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Wed, Dec 10, priced at $179 just found
Frontier Airlines
Thu, Dec 4 - Sat, Dec 6
ORD
Chicago
PDX
Portland
$181 Roundtrip, found 8 hours ago
$181
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Sat, Dec 6, priced at $181 found 8 hours ago
Delta
Tue, Dec 2 - Thu, Dec 11
ORD
Chicago
PDX
Portland
$204 Roundtrip, found 17 hours ago
$204
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Dec 2 from Chicago to Portland, returning Thu, Dec 11, priced at $204 found 17 hours ago
United
Tue, Dec 9 - Thu, Dec 11
ORD
Chicago
PDX
Portland
$206 Roundtrip, found 8 hours ago
$206
Roundtrip
found 8 hours ago
Select United flight, departing Tue, Dec 9 from Chicago to Portland, returning Thu, Dec 11, priced at $206 found 8 hours ago
Southwest Airlines
Sat, Dec 6 - Thu, Dec 11
ORD
Chicago
PDX
Portland
$208 Roundtrip, found 1 hour ago
$208
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Chicago to Portland, returning Thu, Dec 11, priced at $208 found 1 hour ago
American Airlines
Tue, Jan 27 - Wed, Jan 28
ORD
Chicago
PDX
Portland
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jan 27 from Chicago to Portland, returning Wed, Jan 28, priced at $217 found 1 hour ago

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

August is typically the cheapest month to fly

From $105 - $258 per traveler.

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 $305
PDX
Portland Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $305
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, Sun Country Airlines, United
Roundtrip price
$134
Distance
1734 mi
Average flight time
3 hours 12 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 December. 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 $65 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?
Lock in a cheap one-way flight from $65 or cheap return flight from $150 from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
December is the cheapest month to fly from ORD to PDX. Timing your trip outside of the busy season is often the key to scoring lower fares.
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 O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX)?
Alaska Airlines and United Airlines are popular airlines offering competitive fares. Remember that flight prices from O'Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX) can change based on departure dates, demand and how early you book. With Expedia's search tool, you can easily find a ORD to PDX flight that suits your plans and budget.
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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*Available to One Key members.