$87 Cheap flight deals from Portland (PDX) to Chicago (CHI)

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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 $87 One Way, $148 Round Trip from Portland to Chicago

Prices starting at $148 for return flights and $87 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.

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
Qatar Airways, Alaska Airlines, Air Canada, SAS, Iberia, Brussels Airlines, Swiss, Lufthansa, United Airlines
Earliest Flight Arrival
8:06PM UTC
Latest Flight Arrival
12:57PM 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.

Frequently asked questions

Are there non-stop flights from Portland to Chicago?
Buckle up and enjoy a worry-free flight on board one of the 3 airlines that fly straight from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD). We’ve put together a list of reliable carriers to book with:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from Portland to Chicago?
The shortest flight time from Portland to Chicago is 4 hours and 35 minutes, which gives you ample time to enjoy a red wine or get absorbed in a good movie.
What airlines fly from Portland to Chicago most frequently?
Consider booking a flight with United Airlines (UA), which flies frequently along this route. This airline offers 152 flights each month between Portland, OR (PDX-Portland Intl.) and O’Hare Airport. Also check out the great fares from American Airlines (AA). Offering 52 flights every month between Portland and Chicago, they make the journey just as delightful as the destination.
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 2021 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 from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. 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.