Origin Airport

Portland

Destination Airport

Chicago

Number Of Airlines Serving

Distance

1734 mi

Shortest Flight Departure Time

7:00AM CDT

Shortest Flight Departure Date

Oct 8

Flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) - Frequently Asked Questions

Are there non-stop flights from PDX Airport to Chicago, IL (ORD-O'Hare Intl.)?

Yes, if you're flying from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.), you'll only have one flight number to keep in mind. And even better — there are 3 airlines that offer direct services for you to pick from. Reputable ones include:

United Airlines
Alaska Airlines
American Airlines

What is the shortest flight from PDX Airport to Chicago, IL (ORD-O'Hare Intl.)?

Use the opportunity to sit back and relax on your way from Portland to Chicago. The shortest flight time from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) is 3 hours and 44 minutes, which gives you lots of time to enjoy a drink or lose yourself in a gripping novel.

How many hours flight from PDX Airport to Chicago, IL (ORD-O'Hare Intl.)?

Make yourself nice and comfortable, because the average flight time from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) is 4 hours and 27 minutes. Enjoy some wine with your meal, finally finish that book ... You'll have enough time to kick back and enjoy the ride.

If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL (ORD-O'Hare Intl.)?

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, IL (ORD-O'Hare Intl.) 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, IL (ORD-O'Hare Intl.) with flexible change policies?

In most cases you'll have the option to reschedule your flight to Chicago, IL (ORD-O'Hare Intl.) 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 airlines have the most flights from PDX Airport to Chicago, IL (ORD-O'Hare Intl.)?

While there are numerous airlines that fly from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.), there are a couple that stand out in the popularity stakes. American Airlines (AA) is one of the finest and has 83 flights every month. Alaska Airlines (AS) will also take you to your destination in comfort. Offering 95 flights per month between Portland and Chicago, it's another traveler favorite.

Mar 6, 2020

The flight was canceled. Not very satisfied with how Alaska Airlines decided to make it up to me.

Nov 16, 2019

This flight was delayed so long because they didn't have a flight crew. Because of the delay I would miss my connection, and therefore had to find a new flight.

Sep 17, 2019

A true disappointment

Aug 13, 2019

Ran into every delay/obstacle possible

Jan 15, 2019

Let’s start with you selling me a ticket with no carry on allowed! Then can not pick seats! Terrible flight attendants had to beg for water no drink service, then plane was in the 80’s and would not cool it down. United sucks

Sep 1, 2018

Almost didn’t get on the flight stressful we left late made my connecting flight too tight

Aug 4, 2018

Our flight was delayed 1 hour and 20 minutes. We lost our connecting flight and were left with few options other than to fly to Chicago not knowing how we will get to Indianspolis since the soonest flight we could get wasn't until 6:30. In flight crew did not apologize for the delay nor did the people at the gate. Instead a man in a yellow vest lectured us about how it was OUR job to get the plane to leave quickly unaware of the irony of what he was saying. He works for United and it was their job to get to Indianapolis on time and they failed. He should have reframed his words -- something like I know you're upset with the delay and need to make connections and this will make things go faster. Customer service at O'Hare was not helpful and would not pay for a rental car. The majority of United employees we dealt with seemed to really lack empathy for employees. I almost took Delta because of the longer lay over (3 hours as opposed to 1) and I really regret taking United. If it wasn't for the fact that my boyfriend has family in Indiana we would be stranded at O'Hare right now. Another United flight leaving PDX also got delayed.

Jul 8, 2018

Had I known about all their fees for picking a seat and bringing a carry on, I would have picked a different airline and saved money. They’re not cheap, and their ticket prices are a lie.

Jun 29, 2018

My flight was cancelled, and I was offered to rebook 3 days later. I had to book another flight the next day with United and get a hotel room. Spirit offered no assistance nor apology.

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PDX to ORD Route Info

Flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) - Frequently Asked Questions