Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap Flight Deals From Portland (PDX) to Chicago (CHI) Starting at $104

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This Weekend's Flight Deals from Portland to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $104 One Way, $185 Round Trip from Portland to Chicago

Prices starting at $185 for return flights and $104 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.

Chicago economy flight packages

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Residence Inn Chicago Downtown/Loop
W Chicago - City Center
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More About Flying To Chicago from Portland

Route Information for Flights from Portland to Chicago

Origin Airport IATA Code PDX
Destination Airport IATA Code CHI
Distance 1734 mi
Direct Flight Airlines American Airlines, Qatar Airways, Alaska Airlines, Air Canada, LOT - Polish Airlines, Aer Lingus, Finnair, SAS, SWISS, Lufthansa, United Airlines, British Airways
Earliest Flight Arrival 7:43PM UTC
Latest Flight Arrival 1:15PM UTC

Heading to Chicago from Portland

If you’re ready to book flights from Portland to Chicago, use Orbitz.com 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 Orbitz.com 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.

Flights from Portland to Chicago - Frequently Asked Questions

Am I able to catch a flight from Portland to Chicago now?

Our Covid-19 Travel Advisor will help you with questions about quarantine requirements and travel restrictions when taking a flight from Portland to Chicago.

Are there non-stop flights from Portland to Chicago?

You'll find 3 airlines that fly nonstop from Portland Intl. Airport (PDX) to O'Hare Airport, so get ready to hit that beautiful "book" button. One of these carriers will have your perfect flight:

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

From Portland, the distinctive sights and sounds of Chicago are at least 4 hours and 50 minutes away. Choose your favorite seat, or perhaps even upgrade to one with more legroom, and fly to your destination in total comfort.

What airlines fly from Portland to Chicago most frequently?

The carriers that fly the most frequently between Portland Airport and O'Hare Airport include United Airlines (UA). This well-known option operates 69 flights on the route each month. If you need some more options, check out the fares with American Airlines (AA), which has 60 flights from Portland to Chicago each month.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Chicago with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.