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Fares from $64 One Way, $170 Round Trip from Portland to Chicago

Prices starting at $170 for return flights and $64 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Chicago from Portland

Flights from Portland to Chicago - Frequently Asked Questions

Are there non-stop flights from Portland to Chicago?

You betcha. As a matter of fact, there are 3 airlines that fly direct from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.). Book a ticket with one of these carriers:

  • United Airlines
  • Alaska Airlines
  • American Airlines
What is the shortest flight from Portland to Chicago?

From Portland, the distinctive sights and sounds of Chicago are at least 3 hours and 56 minutes away. Choose your favorite seat, or perhaps even upgrade to one with a bit more legroom, and travel to your destination in total comfort.

What airlines fly from Portland to Chicago most frequently?

United Airlines (UA) is one of the carriers with the most flights from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.). It offers 52 services on this route every month. Taking a vacation is one of life's biggest pleasures, and this carrier will get you to your destination quickly and safely. If you'd like more options, take a look at the fares with Alaska Airlines (AS), which has 50 flights from Portland to Chicago each month.

Route Information for Flights from Portland to Chicago

Origin Airport IATA CodePDX
Destination Airport IATA CodeCHI
Distance1734 mi
Direct Flight AirlinesAmerican Airlines, Qatar Airways, Alaska Airlines, British Airways, Gulf Air
Earliest Flight Arrival10:21PM UTC
Latest Flight Arrival11:02PM UTC

Flights Review

Feb 24, 2020

I will definitely use Alaska Air again!

Feb 23, 2020

Portland Airport is Great! Easy TSA process, keep shoes and belts on.

Jan 25, 2020

Seats were small. I felt cramped. I would fly JetBlue if I could. Landing was HARD

Jan 13, 2020

loved it, very comfy flight.

Jan 12, 2020

Handles on my walker got broken by baggage handlers.

Dec 27, 2019

Too cramped! Not enough space between rows seats are too small.

Dec 22, 2019

Check in agent was super helpful and she even got me a better seat at the gate! Thanks!!!

Dec 4, 2019

Acceptable experience on flight. Nothing great

Nov 29, 2019

and it arrived early! good job team

Nov 26, 2019

I have an ESA, and the agent made my flight easy and stress-free. Thank you!

Heading to Chicago from Portland

If you’re ready to book flights from Portland to Chicago, use to make sure that you’re getting the best deals on fares. Portland is an artsy, beautiful city known for its quirky sensibilities, and Chicago has a fast-paced, big-city energy that manages to remain decidedly mid-Western, making it a perfect vacation destination.

Leaving Portland’s Airport

Flights out of Portland leave from Portland International Airport. Located seven miles northeast of town, a taxi service like Radio Cab will cost you about $35 from the center of the city and will take about twenty minutes. Public transportation is available via the MAX Red Line, which travels from the airport into downtown Portland every fifteen minutes. The fare is $2.05, and you can purchase tickets from the automated machines in the airport lobby. If you’re driving yourself to the airport, parking at the terminal is $3 per hour and $18 per day.

Arriving in Chicago

Your flight to Chicago will arrive at O’Hare International Airport, one of the busiest airports in the world. There are many ways to get from the airport into town. There are plenty of taxis at the airport, and the average fare is around $40 to the center of town. The trip will take anywhere from thirty minutes to over an hour, depending on traffic. The Blue Line train runs from the airport to town and costs $2. There are hundreds of things to do in Chicago, but you can start off slowly by catching one of the thrilling performances at the Lookingglass Theater Company. If you’re a baseball fan, check out a Cubs game at Wrigley Field, a stadium so revered it’s worth the visit even if there isn’t a scheduled game. Chicago summers are hot and humid, with temperatures frequently reaching around 90°F. Winter temperatures frequently dip below 30°F, and the infamous Chicago wind often makes it feel much colder. Spring and summer are the best times to go, thanks to the sheer number of festivals and events that take place at those times. If you can handle the cold, you can score great deals on hotels during the winter.

Off to Chicago

Book your flights from Portland to Chicago through so that you can rest comfortably knowing that you’re getting the best deals on flights and hotels. Chicago has tons of activities for the adventure-bound and those who prefer to watch the action, so your only focus should be fitting it all in.

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.