Cheap Flight Deals From Portland (PDX) to Chicago (CHI) Starting at $40

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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 $40 One Way, $79 Round Trip from Portland to Chicago

Prices starting at $79 for return flights and $40 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

Swissotel - Chicago
Fairmont Chicago at Millennium Park
Hotel Lincoln, part of JdV by Hyatt
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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, Air Canada, LOT - Polish Airlines, Aer Lingus, SWISS, United Airlines, Alaska Airlines, Finnair, SAS, Iberia, Malaysia Airlines, Lufthansa, Gulf Air, British Airways
Earliest Flight Arrival 7:34PM UTC
Latest Flight Arrival 1:05PM 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

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.