$90 Cheap United flights Portland (PDX) to Chicago (ORD)

Scoring cheap one-way United Airlines flights from PDX to ORD from $90 on Expedia couldn’t be easier — just filter by “Price (lowest to highest).” Alternatively, check out our affordable return fares from $179 for your next adventure.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

United Airlines flights to Chicago are usually cheaper in the off-peak months of January and February. Whether you’re in search of a round-trip or one-way ticket, you could land a better deal then.

To find cheap United Airlines fares from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD), start searching one to three months before your planned departure. Reserving domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also affect the overall cost. Sunday is generally the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking on a Sunday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

United Airlines offers direct flights from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD), with 17 departures every week. Just apply the “Nonstop” and “Airline” filters while searching on Expedia to see all direct United Airlines flights to ORD.

On average, it takes 4h 1m to fly nonstop from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD) with United Airlines.

If you’re looking for flexibility, Sunday offers the most choice for United Airlines flights from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD). You can pick from 3 different departures.

The earliest United Airlines flight from PDX to ORD departs at 7:00AM UTC-8, arriving at 1:01PM UTC-6. If you’d like to set off later, the last United Airlines flight leaves PDX at 11:59PM UTC-8 and lands at ORD at 6:00AM UTC-6. Flying before noon is often a smart choice as morning and mid-morning flights are least likely to face cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

United Airlines flights from Portland Intl. Airport (PDX) to Chicago arrive at O’Hare Intl. Airport (ORD) and Midway Intl. Airport (MDW). The primary Chicago gateway serviced by this airline is ORD. It’s always worth considering flights arriving at nearby airports on Expedia as they may offer cheaper prices.

Journey from PDX to ORD with United Airlines and you’ll enjoy a host of benefits starting with a rewarding loyalty program. When booking through Expedia as a United Mileage Plus and One Key™ member, you may also earn OneKeyCash™* to redeem on select future travel purchases.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

You’ll likely be on a Boeing 737-900 or a Boeing 737-800 when flying United Airlines from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD). However, keep in mind that a different plane may be assigned due to operational factors.

It’s generally possible to modify or cancel your flight, although there may be additional fees if your booking was made over 24 hours ago. Need flexible options? Make use of Expedia’s “Changes included” and “No cancel fee” filters to find flights that won’t penalize you if you need to revise your plans. To update your booking, go to “Trips,” select your flight and click on “Manage Booking” for more details.