How much is a plane ticket to Chicago (ORD) from Portland (PDX)?

Cost can range from $95 to $805, prices for PDX to ORD do fluctuate more than most routes in US. Remember, the sooner you book, the more you'll be able to save. Book now.

How long is the flight from PDX to ORD?

If you're able to take the direct flight (which is offered by United Airlines), you will be able to leave PDX at 11:24 PM PDT and get to ORD at 5:04 AM CDT (three hours and 40 minutes). Remember, there is a time change of two hours.

What is the cheapest day to fly to Chicago?

If you are wanting to save some cash, look at Oct 29th. As of Oct 18th, it's showing the cheapest ticket at $95. That is 58% below the average for this route, so you can spend your savings on an adventure rather than the flight.

What is the cheapest airline flying from Portland to Chicago?

Spirit Airlines strives to keep costs low for their passengers over the next three months. Fares are being booked at just $95, which is quite a deal when compared to the more expensive bookings of $805.

How long do most people stay in Chicago?

Of course, you're not most people, but if you were, you'd stay around five days.

Can I change the date of my flight?

Yes, you can change your departure date. If you would like to save a little cash in doing so, the lowest-cost day to fly in November is Thursday. If you like to go with the flow, you may just find that you can pocket some extra money that you can use for future trips.

Which airline has the least delays from Portland to Chicago?

PDX to ORD currently has 4 stars out of 5, earning it one of the best performances in the world. You can fly worry-free on this route. The best measurement of overall promptness combines both on-time percentage and total delay minutes.

How many flights are there per day from Portland to Chicago?

The number of flight times varies by day, but on average, PDX to ORD sees 17 different options. You’ll have more choices on this route than most other routes departing US.

What day has the most flight time options?

When you’re flying from PDX to ORD, the day with the most flight times is Thursday, with 20 different options. However, with 12 flight times, Saturday doesn't offer quite as many options when finding that perfect departure time.

What is the cheapest day to fly?

The cheapest day to fly from Portland to Chicago is on Thursday. So, if you would like to save a little money on your next holiday look for flights on that day.

How long does it take to fly from Portland to Chicago?

This flight takes around three hours and 40 minutes via United Airlines (remember, there is a time change of two hours).

$64 Cheap flights from Portland (PDX) to Chicago (ORD) (2021)

Cheap Flights from Portland Intl. to O'Hare Intl.

Prices were available within the past 7 days and starts at $64 for one-way flights and $111 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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Flights from Portland to Chicago: Reviews from verified customers

Mar 7, 2020

I had to pay for a backpack which was annoying and inconvenient. It was not the correct side according to the agent

A verified traveler

Portland to Chicago · United

Feb 22, 2020

Need more leg room

A verified traveler

Portland to Chicago · United

Feb 19, 2020

Wish there were power/usb outlets in all seats

A verified traveler

Portland to Chicago · United

Feb 19, 2020

Even though the plane was delayed, our steward was wonderful. When some tempers were running short, he was able to reframe the situation and regain control so that we had a good, safe trip and deboarding.

A verified traveler

Portland to Chicago · United

Feb 16, 2020

Staff was so warm and welcoming and wanted to be there! Such a different experience than united airlines. Seats were comfortable even in row 30. United has jammed in more seats which makes it a uncomfortable tight miserable experience.

A verified traveler

Portland to Chicago · Alaska Airlines

Jan 30, 2020

Did not appreciate 30.00 fee for my carry on device .

A verified traveler

Portland to Chicago · United

Jan 9, 2020

Alaska Airlines is an amazing company!

A verified traveler

Portland to Chicago · Alaska Airlines

Jan 1, 2020

I was really neither happy or sad about my flight. You need to give a neutral option.

A verified traveler

Portland to Chicago · United

Dec 29, 2019

Flight attendants Eileen and Fran (flight 690) were an example of what great employees should be like, from when we boarded to when we exited, we wanted for nothing. Just great overall

A verified traveler

Portland to Chicago · Alaska Airlines

Dec 4, 2019

Need more space bigger restrooms and better seating options

A verified traveler

Portland to Chicago · United

Flight from Portland to Chicago route information
Origin Airport	Portland Intl.
Destination Airport	O'Hare Intl.
Airlines Serving	Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Spirit Airlines, Sun Country Airlines, United
Flight Price	$111
Distance	1734 mi

Frequently asked questions

Policies will vary from partner to partner, but many of them cover travel to highly impacted areas. The dates and destinations change frequently as more is learned about the situation, so it’s important for travelers to check in with the airline if they have an upcoming trip. Please visit our Customer Support Portal to learn more about what policies are available for your flight from Portland to Chicago

Portland to Chicago Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Portland to Chicago offer the perfect respite. Not only does exploring Chicago provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Portland to Chicago may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from PDX to ORD today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Chicago are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Chicago more flexbily many prefers to purchase one-way tickets with options to take different airlines. One way ticket to Chicago is $64 now!