￥23,070 Cheap Flights from Portland (PWM) to Chicago (ORD)

View ￥23,070 flight on Fri, Jun 12, 2026Opens in a new window

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

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Cheap Flights from Portland to Chicago (PWM-ORD)

Prices were available within the past 7 days and start at ￥23,070 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Find the cheapest month to fly from Portland (PWM) to Chicago (ORD)

October is typically the cheapest month to fly

From ￥23,263 - ￥60,226 per traveler.

Frequently asked questions

How much is a flight from Portland Intl. Jetport to ORD?
If you're traveling between PWM and ORD, round-trip flights start from . This figure is based on fares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang around. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from PWM to O'Hare Airport?
Every air carrier has its own set of terms and conditions. If you do decide to cancel, follow the easy instructions on our Customer Service Portal.
How do I find cheap flights from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Portland Intl. Jetport to O'Hare Intl. Airport (ORD) flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD)?
It only takes about 2 hours and 48 minutes to journey from PWM to O'Hare Intl. Airport (ORD) — just enough time for a power nap. You'll be landing in Chicago by the time you wake up.
How far is the flight from PWM to ORD?
A flight distance of just 1,450 kilometers separates Portland and Chicago. Once you're up in the skies, you won't have time to do much more than read the magazine in your seat pocket.
Which airlines fly direct from PWM to ORD?
United Airlines (UA) is one of the preferred choices for many travelers flying between PWM and ORD. Select from the 60 flights it offers on this route each month. You could also have a look at the fares available with American Airlines (AA). It operates 52 flights every month between Portland and Chicago.
Are Portland Intl. Jetport to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Flight prices are constantly going up and down, so not always. While last-minute deals between Portland Intl. Jetport and ORD are possible, it also makes sense to keep a close eye on prices well before you fly. In fact, some airlines publish their prices up to 12 months before the departure date. Expedia is continuously updating the biggest bargains around, so keep checking back and be ready to book when the price is low.

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

Portland to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Portland to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with PWM to ORD flights that won’t make your bank account wince. Ready to temporarily leave behind Portland for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to ORD with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Portland to Chicago Flights
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