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

Finding cheap one-way United Airlines flights from PWM to ORD from $90 on Expedia is easy — just filter by “Price (lowest to highest).” Or check out our affordable round-trip fares from $189 for your next exciting vacation.**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 often more affordable in the low-season months of January and February. Whether you’re searching for a one-way or a return ticket, you could land a better deal then.

Search for cheap United Airlines flights from Portland Intl. Jetport Airport (PWM) to O’Hare Intl. Airport (ORD) one to three months ahead of your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare type and journey, the ideal day to book a domestic flight is usually Sunday and the most expensive tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**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.

Easily travel from Portland Intl. Jetport Airport (PWM) to O’Hare Intl. Airport (ORD) on any of United Airlines’s 7 weekly direct flights. Use Expedia’s “Nonstop” and “Airline” filters to find the United Airlines flight that’ll take you to ORD at a time that suits you.

Depart Portland Intl. Jetport Airport (PWM) for O’Hare Intl. Airport (ORD) on a direct United Airlines flight, and you’ll be airborne for approximately 3h 14m.

The earliest flight from PWM to ORD with United Airlines departs at 4:10PM UTC-5. You’ll land at 6:24PM UTC-6. The final United Airlines flight of the day takes off at 4:10PM UTC-5 and arrives at 6:24PM UTC-6. With around 20% fewer cancellations for early and mid-morning flights, heading out early is often the wisest option.**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.

O’Hare Intl. Airport (ORD) is the primary Chicago hub for United Airlines flights from Portland Intl. Jetport Airport (PWM).

A rewarding loyalty program and the chance to rack up points through United Mileage Plus are the start of the reasons to travel from PWM to ORD with United Airlines. Plus, when you sign up to our One Key™ program, you can receive OneKeyCash™* in addition to any airline loyalty program earnings. It’s yours to spend on your next adventure.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Most likely, you’ll catch an Embraer 175 for your United Airlines flight from Portland Intl. Jetport Airport (PWM) to O’Hare Intl. Airport (ORD). However, you could be switched to an alternative aircraft if there’s an operational need.

You can usually change or cancel your flight, although there may be a charge if you made your booking more than 24 hours ago. Want to keep your options open? Use our “No cancel fee” or “Changes included” filter to find flights that won’t charge you extra if you need to alter your plans. To make modifications, visit “Trips,” select your flight and click on “Manage Booking” for further information.