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

View $81 flight on Mon, Aug 18, 2025Opens 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 $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
Fri, Aug 15 - Tue, Aug 19
PDX
Portland
ORD
Chicago
$162 Roundtrip, found 9 hours ago
$162
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Fri, Aug 15 from Portland to Chicago, returning Tue, Aug 19, priced at $162 found 9 hours ago
Spirit Airlines
Sat, Aug 16 - Tue, Aug 19
PDX
Portland
ORD
Chicago
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Portland to Chicago, returning Tue, Aug 19, priced at $169 found 1 hour ago
Spirit Airlines
Thu, Aug 14 - Tue, Aug 19
PDX
Portland
ORD
Chicago
$170 Roundtrip, found 5 hours ago
$170
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Thu, Aug 14 from Portland to Chicago, returning Tue, Aug 19, priced at $170 found 5 hours ago
Spirit Airlines
Wed, Aug 20 - Tue, Aug 26
PDX
Portland
ORD
Chicago
$174 Roundtrip, found 9 hours ago
$174
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, Aug 20 from Portland to Chicago, returning Tue, Aug 26, priced at $174 found 9 hours ago
Spirit Airlines
Mon, Aug 18 - Tue, Aug 19
PDX
Portland
ORD
Chicago
$176 Roundtrip, found 1 hour ago
$176
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Mon, Aug 18 from Portland to Chicago, returning Tue, Aug 19, priced at $176 found 1 hour ago
United
Sat, Aug 30 - Sun, Aug 31
PDX
Portland
ORD
Chicago
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Aug 30 from Portland to Chicago, returning Sun, Aug 31, priced at $179 found 6 hours ago
American Airlines
Sat, Aug 30 - Sun, Aug 31
PDX
Portland
ORD
Chicago
$182 Roundtrip, found 6 hours ago
$182
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Portland to Chicago, returning Sun, Aug 31, priced at $182 found 6 hours ago
Alaska Airlines
Sat, Aug 30 - Sat, Sep 6
PDX
Portland
ORD
Chicago
$183 Roundtrip, found 1 hour ago
$183
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Sat, Aug 30 from Portland to Chicago, returning Sat, Sep 6, priced at $183 found 1 hour ago
Spirit Airlines
Wed, Aug 20 - Sat, Aug 30
PDX
Portland
ORD
Chicago
$184 Roundtrip, just found
$184
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Aug 20 from Portland to Chicago, returning Sat, Aug 30, priced at $184 just found
Southwest Airlines
Sat, Aug 30 - Sun, Aug 31
PDX
Portland
ORD
Chicago
$190 Roundtrip, found 6 hours ago
$190
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Portland to Chicago, returning Sun, Aug 31, priced at $190 found 6 hours ago

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

August is typically the cheapest month to fly

From $88 - $192 per traveler.

Graph displaying average flight prices per month

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. Cheapest and Closest option available. Average driving time to city center is 16 minutes. Flights from $352
MDW
Midway Intl.
CheapestClosest
Average driving time to city center16 min
Flights from $352
Flights from Portland (PDX) to Chicago (ORD)
Origin airport
Portland Intl.
Destination airport
O'Hare 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
6 hours 3 mins

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 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 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.

 

Frequently asked questions

How much does a flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) cost?
You can find affordable return tickets from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) starting from $181. Snag a seat and get ready for takeoff. 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 American Airlines and Southwest Airlines flight leaving PDX on August 12 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from PDX to ORD?
The cheapest flights from PDX to ORD 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 Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Jump on a direct flight with United Airlines and journey straight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from PDX to ORD?
Book a flight from PDX to ORD with Alaska Airlines. This airline currently offers the lowest one-way fare for this route, starting at $90. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from PDX on August 31 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Every day on average, 3 nonstop flights take off from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD). Choose the departure that best fits your itinerary.
What are the most popular departure times for flights from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
The 7 AM departures from PDX to ORD are the most sought after. Greater demand means you'll likely pay more for these departures. If you're hoping to save money, pick a less crowded time to fly.
What day of the week has the most flights from PDX to ORD?
If you travel on a Thursday, you'll get the widest range of choices for flights from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
The first flight of the day departing from Portland Intl. Airport (PDX) is at around 7:00AM UTC-8. Catch this flight and you'll land at O'Hare Intl. Airport (ORD) at approximately 1:01PM UTC-6. The entire trip takes 4h 1m.
How long does it take to fly from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Flights from PDX to ORD have an average travel time of 4 hours and 1 minute. The total distance between these two airports is 1,750 mi.
What airline has the least delays from PDX to ORD?
Consider booking with American Airlines if you'd like to fly straight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) without any holdups. This airline has the best track record for punctuality, with an on-time performance of 89%. Want to be updated if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
Book a flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of cancellations. Later departures are on average 22% more likely to be canceled.**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 Chicago from Portland Intl. Airport (PDX)?
Board a direct flight from Portland Intl. Airport (PDX) to Chicago and land at O'Hare Intl. Airport (ORD). An alternative point of entry into this city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until just before your trip to book a flight from PDX to ORD generally means paying more. While it's possible to find some last-minute offers, there's no guarantee. Keep your travel plans flexible for a better chance of landing a bargain.
Is it cheaper to book a PDX to ORD flight and hotel package?
You can save money by booking a PDX to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've chosen your preferred accommodations and flights, consider adding extras including tours, activities and car rentals.
Can I cancel or change the date of my flight from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)?
If you reserved your PDX to ORD 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, go to our Customer Service portal if you want more information.

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