£118 Cheap Flights from Portland (PDX) to Chicago (ORD)

You can find cheap one-way flights from £118 and cheap return flights £221 PDX to ORD with Expedia. One-way flights typically cost between £129 and £461. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when PDX to ORD ticket fares go up or down.

September is typically the cheapest month to fly from Portland International Airport (PDX) to O'Hare International Airport (ORD), with average return fares around £213. September often sees lower prices as the peak summer travel season winds down, and before the holiday rush begins, leading to reduced demand and more competitive airline pricing. February and August are also good months to find deals on this route.

There are 3 airlines offering direct flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.). Here are the top carriers:
* United operates 46 direct flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
* American Airlines operates 29 direct flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.
* Qatar Airways operates 7 direct flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) every week.

Sun Country Airlines is one of the cheapest airlines offering connecting return flights on this route, with prices starting from around £192. American Airlines is one of the cheapest airlines offering nonstop return flights from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.), with prices starting from around £223 for flights that can be booked for departure within the next year. These prices are per adult for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from Portland, OR (PDX) to Chicago, IL (ORD), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

The earliest flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 12:05 AM local time. This service is usually operated by American Airlines. This is a seasonal service, active in June and July. An early departure like this can be really handy if you want to maximise your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

A non-stop flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically takes around 4 hours 18 minutes. This route covers a distance of approximately 2,791 kilometers. If you opt for a flight with one stop, your journey will usually be longer, taking about 8 hours. Flights with two or more stops will extend your travel time even further, to around 15 hours 30 minutes. Keep in mind that actual flight times can vary due to factors like wind patterns and air traffic.

Select the "Business class" and "First class" filters when looking for Portland, OR (PDX) to Chicago, IL (ORD) flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

It's easy to earn miles on a Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

If you're planning to travel to Chicago from Portland Intl. (PDX), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like San Francisco Intl. (SFO), Sky Harbor Intl. (PHX), or Sacramento Intl. (SMF) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Portland, OR (PDX-Portland Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Portland, OR (PDX) to Chicago, IL (ORD) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.