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Selected fares from Portland to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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.


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.

*Savings based on all holiday package bookings with Flight + Hotel on from January through December 2017, 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Dec 23, 2018

Cranky staff, talk to us like children, really awkward to listen to

Dec 21, 2018

The desk staff at gate F20 (female) and my gate F22 (male) were some of the nicest people I've ever encountered! I just enjoyed listening to them go above and beyond over and over! Seriously hard workers. Every person the woman helped she treated like a dear family member. I wish I knew her name!

Dec 17, 2018

Service was a little slow and only came by once on a 3+ hour flight. Would've also liked a small snack, but only got drink service.

Nov 27, 2018

just good all around -- and we usually fly American!

Nov 22, 2018

Not sure why the 2 1/2 hour delay. But, everything else was good

Nov 6, 2018

I upgraded and paid $72 for an exit row. After every one seated a man asked to sit in exit row and so his was free.

Oct 24, 2018

Service wasn’t bad. The flight attendants were just there. They didn’t go out of their way to be personable. It could be because it was a red eye flight. The only real complaint is you could not hear anything the flight attendant said on the loudspeaker. She was very soft spoken and did not speak clearly.

Oct 9, 2018

Would like my $50 refund for being charged for my carry-on! Could not believe it and was NOT happy about it. Everyone else had a carry on, and mine was even smaller in size. Also, while waiting to board it was announced if anyone wanted to "check" their baggage they would do it for free!!! Unbelievable!!!

Oct 3, 2018

I asked for help at check in, refused to, I had to use.kiosk....told me I had to pay for a.checked bag, I couldn't take my carryon....all incorrect info. She just walked away from me, and I said so you are refusing to help me and she said yes. I found another agent to help althought she too was rude and told me I shouldn't ever buy an economy plus ticket if I wanted any service from them in the future.

Oct 3, 2018

The service staff offered only beverages on a four-hour flight. I wanted to buy food.