Cheap Flights from Portland (PWM) to Chicago (ORD)

Popular airlines from Portland Intl. Jetport Airport (PWM) to Chicago O'Hare Intl. Airport (ORD)

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Frequently asked questions

How long does it take to fly from Portland Intl. Jetport Airport (PWM) to ORD?
With United Airlines, a direct flight takes roughly 2 hours and 59 minutes. Secure a seat on the 9:12AM flight from Portland Intl. Jetport and reach O'Hare Airport at 11:11AM. Pick up an epic deal on this route when you use Expedia to arrange your trip.
Is it cheaper to buy a plane ticket from PWM to ORD last minute?
When it's time to book your flights, it's better to be prepared. While you may be able to score a deal on a Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) flight at the last minute, fares usually don't get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to book a domestic flight is between 28 – 35 days ahead. For international journeys it's between three and four months.
What airline has the least delays from Portland Intl. Jetport to O'Hare Intl. Airport (ORD)?
If you'd rather not be waiting around for hours — or worse, your vacation plans left in tatters because of a flight delay — fly with United Airlines. Around 100% of its PWM to ORD services are on time. You can check your flight status before you leave for the airport through the free Expedia App. It'll also give you real-time alerts about any gate changes, luggage carousel numbers and how to get to your hotel. Think of it as a handy travel companion in your pocket!
What airports do you fly into for Chicago from Portland?
From Portland, you can fly into Chicago through O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT). Do some research into which airport is the most convenient for you before making your decision. If you settle on O'Hare Intl. Airport (ORD), it's approximately 26 kilometers northwest of the center of the city. Use the dollars you save when booking your airfare with Expedia to uncover the city's top sights, such as Wrigley Field and Millennium Park.
What are the most popular departure times for flights from Portland Intl. Jetport to ORD?
The most popular departure times for journeys from PWM to ORD fall between 4:00 PM - 5:00 PM on United Airlines. Our advice is to zoom off in the morning. The earlier you do, the better your chances of arriving on time with lighter air traffic in the sky.
Can I change the date of my flight from Portland Intl. Jetport Airport (PWM) to O'Hare Airport?
Quickly and easily make changes to your Portland Intl. Jetport Airport (PWM) to ORD flight through the Expedia Trips portal. Before you amend times or dates, read the ticket rules in your itinerary to see what you can do and if charges apply. Some airlines have a change fee per person, plus any difference in prices. But if you booked in the last 24 hours, you may be able to cancel for free and organize new flights. You can also check out our Customer Service portal for more information and to chat with our Virtual Agent.

Travel information

Travel information

Origin airport
Portland Intl. Jetport
Destination airport
O'Hare Intl.
Distance
1435 km
Average flight time
2 hours 7 mins

Book with confidence

Book with confidence

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 to 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 flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Chicago is now!

Portland to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia