
Popular airlines from Portland International Airport (PDX) to Chicago
- Alaska Airlines
Alaska Airlines
- Delta
Delta
- Southwest Airlines
Southwest Airlines
- American Airlines
American Airlines
- United
United
- Frontier Airlines
Frontier Airlines
- Sun Country Airlines
Sun Country Airlines
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Today's featured flight deals from Portland International Airport (PDX) to Chicago
- Portland (PDX) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Sun, Nov 23 at 11:00pm from Portland, arriving on Mon, Nov 24 at 5:01am in Chicago.Returning on Fri, Nov 28 at 7:00am from Chicago, arriving at 9:39am in Portland.Select Alaska Airlines flight departing on Sun, Nov 23 at 11:00pm from Portland, returning on Fri, Nov 28 at 7:00am from Chicago priced at $25735% less than typical$257
- Portland (PDX) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Fri, Nov 21 at 11:00pm from Portland, arriving on Sat, Nov 22 at 5:01am in Chicago.Returning on Wed, Nov 26 at 7:05pm from Chicago, arriving on Thu, Nov 27 at 12:30am in Portland.Select Alaska Airlines flight departing on Fri, Nov 21 at 11:00pm from Portland, returning on Wed, Nov 26 at 7:05pm from Chicago priced at $25735% less than typical$257
- Portland (PDX) to Chicago (ORD).American Airlines, nonstop.Departing on Wed, Nov 19 at 11:43am from Portland, arriving at 5:55pm in Chicago.Returning on Sun, Nov 23 at 4:25pm from Chicago, arriving at 11:35pm in Portland.Select American Airlines flight departing on Wed, Nov 19 at 11:43am from Portland, returning on Sun, Nov 23 at 4:25pm from Chicago priced at $35825% less than typical$358
- Portland (PDX) to Chicago (ORD).Alaska Airlines, nonstop.Departing on Mon, Nov 24 at 11:00pm from Portland, arriving on Tue, Nov 25 at 5:01am in Chicago.Returning on Fri, Nov 28 at 7:00am from Chicago, arriving at 9:39am in Portland.Select Alaska Airlines flight departing on Mon, Nov 24 at 11:00pm from Portland, returning on Fri, Nov 28 at 7:00am from Chicago priced at $24735% less than typical$247
- Portland (PDX) to Chicago (ORD).American Airlines, nonstop.Departing on Wed, Dec 10 at 11:37am from Portland, arriving at 5:52pm in Chicago.Returning on Wed, Dec 17 at 8:10am from Chicago, arriving at 10:47am in Portland.Select American Airlines flight departing on Wed, Dec 10 at 11:37am from Portland, returning on Wed, Dec 17 at 8:10am from Chicago priced at $21735% less than typical$217
- Portland (PDX) to Chicago (ORD).American Airlines, nonstop.Departing on Mon, Dec 8 at 1:28pm from Portland, arriving at 7:46pm in Chicago.Returning on Fri, Dec 12 at 9:57am from Chicago, arriving at 12:38pm in Portland.Select American Airlines flight departing on Mon, Dec 8 at 1:28pm from Portland, returning on Fri, Dec 12 at 9:57am from Chicago priced at $23735% less than typical$237
Cheap Flights from Portland to Chicago (PDX-CHI)
Prices were available within the past 7 days and start at $65 for one-way flights and $134 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.










Find the cheapest month to fly from Portland (PDX) to Chicago (CHI)
August is typically the cheapest month to fly
Alternative airports near Chicago
Prices were available within the past 7 days. Prices and availability are subject to change.
Travel information
Origin airport | Portland Intl. |
|---|---|
Destination airport | O'Hare Intl. |
Roundtrip price | $134 |
Distance | 1734 mi |
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 December. 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 $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 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.
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