Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap Flight Deals From Chicago (CHI) to Portland (PDX) Starting at $75

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This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $75 One Way, $101 Round Trip from Chicago to Portland

Prices starting at $101 for return flights and $75 for one-way flights to Portland were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Portland from Chicago

Fly from Chicago to Portland

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Vacation in Portland

Trying to find discount airfare on domestic and international flights can be a time-consuming task for travelers. When searching for flights to Portland, check out Orbitz.com, which will compare the rates of several airlines at once, so you get the best deal available.

Portland Airport Information

The Port of Portland Airport provides the majority of air service to Portland. Several airlines service the airport, including Air Canada, Alaska, American, Delta, Frontier, Hawaiian, JetBlue, Sea Port, Southwest, Spirit, United, US Airways, and Virgin America. On Orbitz.com, you can search the fares of most of these airlines to ensure you receive the best discount available.

Transportation From the Airport

Getting to your hotel or destination from the airport is simple when you take a taxi, rental car, bus, or shuttle. Some hotels offer a free shuttle service if you have a room booked with them. The taxi fare from the airport to downtown Portland is around $30. Car rentals can be purchased at the same time you book your airline tickets on Orbitz.com, and it's another way to save money.

Portland Weather Information

The weather in Portland is typically very pleasant. The average high temperature during the summer is 80 degrees, and in the winter, it's in the upper 30s. Portland receives an abundant amount of precipitation, sometimes unexpected; however, it rarely falls below freezing. Having an umbrella handy is recommended.

Portland Attraction Information

Portland offers many activities and attractions for families to enjoy all year long. The Oregon Zoo, Museum of Science and Industry, and city tours are among a long list of things to do while in Portland. When you search for flights to Portland on Orbitz.com, check out the offers on the many attractions to explore.

Flights from Chicago to Portland - Frequently Asked Questions

Am I able to catch a flight from Chicago to Portland now?

Check out our Covid-19 Travel Advisor for the most comprehensive information on travel restrictions and quarantine requirements when catching a flight from Chicago to Portland.

Are there non-stop flights from Chicago to Portland?

You'll find 3 airlines offering direct services from Chicago, IL Airport (ORD-O'Hare Intl.) to Portland, OR Airport (PDX-Portland Intl.), so get ready to hit that "book" button. One of these carriers will have your ideal flight:

  • United Airlines
  • American Airlines
  • Alaska Airlines
What is the shortest flight from Chicago to Portland?

Traveling from Chicago, IL Airport (MDW-Midway Intl.) to Portland Intl. Airport (PDX) takes at least 4 hours and 56 minutes. Enjoy a wine and read a few magazines — this is the perfect opportunity to simply relax.

What airlines fly from Chicago to Portland most frequently?

The carriers that fly frequently between O'Hare Intl. Airport (ORD) and PDX include United Airlines (UA). This well-known option offers 69 flights on the route every month. American Airlines (AA) also flies from Chicago to Portland. It's another excellent option and offers 56 flights every month.

If I am not able to travel due to COVID-19, can I cancel my flight to Portland?

We get that traveling right now has its challenges, so it's good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Portland have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you'll quickly see what options are available. Our Customer Service Portal is the place to go for more information.

Are there flights to Portland with flexible change policies?

In most cases you'll have the option to reschedule your flight to Portland without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the "no change fees" filter and book with confidence.

What is the cheapest day of the week to fly?

Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.

What is the cheapest month to fly?

We won't keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.

How can I save money on flights?

To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you'll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

*According to flight demand on Orbitz.com from January to December 2020. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.