$56 Cheap Flights from Portland to Chicago

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Portland Intl. to O'Hare Intl.

Amazing PDX to ORD Flight Deals

The cheapest flights to O'Hare Intl. found within the past 7 days were $111 round trip and $56 one way. Prices and availability subject to change. Additional terms may apply.

Best O'Hare Intl. Flight and Hotel Packages

O'Hare Intl. flight + hotel packages - economy flights

Swissotel - Chicago
Sheraton Grand Chicago
Residence Inn Chicago Downtown/Loop
Hotel Lincoln, part of JdV by Hyatt
Hyatt Centric Chicago Magnificent Mile
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FAQs about flights from Portland Intl. Airport (PDX) to O'Hare Intl. Airport (ORD)

Can I catch a flight from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.) right now?

For any present Chicago, IL Airport (ORD-O'Hare Intl.) travel advice and quarantine requirements, go to the Covid-19 Travel Advisor. Look before you arrange your flight, so you don't get caught out.

Are there direct flights from Portland Intl. Airport (PDX) to ORD?

Some trips are all about the journey; other times, the magic is in the destination. But if you just want to get to where you're going fast, multiple airlines provide direct flights from Portland, OR Airport (PDX-Portland Intl.) to ORD, including United Airlines and American Airlines.

If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to ORD, please visit our Customer Service Portal.

How long is the flight from PDX to ORD?

The flight between PDX and O'Hare Airport is typically around 3 hours and 58 minutes. Make your journey comfortable by saving a few podcasts on your laptop or tablet and enjoying them with your seat fully reclined.

What is the flight distance from Portland Intl. Airport (PDX) to Chicago, IL Airport (ORD-O'Hare Intl.)?

You'll have to travel around 1,740 mi from Portland Airport to ORD before you can officially kick off your vacation. Get a beverage when the drink cart rolls by and watch some of your favorite movies. You'll have more than enough time!

What airlines fly from Portland, OR Airport (PDX-Portland Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.)?

There are a few airlines advertising direct flights from PDX Airport to O'Hare Airport. United Airlines (UA) is one of the most reliable, and operates at least 95 flights every month. Another possibility is American Airlines (AA), which has 102 flights each month. The more airlines you consider, the more likely you are to sniff out a great deal.

What airlines have practices regarding COVID-19 in place and use social distancing?

From the moment you enter the departure terminal to when you leave the arrivals terminal, if you're flying with United Airlines, American Airlines or Delta you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.

What is the best day to buy a plane ticket?

This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2020. Wednesday and Friday prices are also good, but you may want to prepare your budget if booking on a Sunday, as data shows the end of the week is when prices are generally at their highest.

What are the cheapest days to fly?

Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2020, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.

How far in advance can you book a flight?

Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2020 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2 weeks to 2 months prior to their travel dates.

How can I save money on airline tickets?

We'll let you in on a secret...You can save big on flights if you mix and match your airlines and fare types. In fact, travelers who booked flights on Travelocity in 2020 saved nearly 40% when their return flights consisted of two different airlines or fare types.

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

Portland Intl. to O'Hare Intl. Flight FAQ

Traveling From Portland Intl.
Traveling To O'Hare Intl.
Shortest Flight Time 7 hours 55 mins
Earliest Departure Time 6:30AM CDT
Latest Departure Time 11:45PM CDT
Lowest Flight Price $111

Route Info

Flight path for flights from Portland International Airport to O'Hare International Airport

1,744.00 miles

Airlines & Aircraft Used on PDX to ORD Flight Routes

Airline Carrier
Alaska Airlines
Airbus A319
Alaska Airlines
Airbus A320-100/200
Alaska Airlines
Airbus A321-100/200
Alaska Airlines
Boeing 737-600 pax
Alaska Airlines
Boeing 737-800 (winglets) pax
American Airlines
Airbus A320-100/200
Delta Air Lines
Boeing 737-600 pax
Delta Air Lines
Boeing 737-700 (winglets) pax
Jet Airways (India)
Fokker 50

Discover our best flights from Portland PDX to Chicago ORD. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 


Find our best return flights from Portland PDX to Chicago ORD at the right price  

Airfares to Chicago ORD from Portland PDX currently cost between $111 and $144. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 


Book one-way flights from Portland PDX to Chicago ORD 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Portland PDX to Chicago ORD on Travelocity starting at $56. Prices and availability subject to change. Additional terms may apply. 


Get to Chicago ORD from Portland PDX quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to ORD from PDX to take around 7 hour(s) 55 min(s).  


Find our cheapest airfares for flights from Portland PDX to Chicago ORD

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to ORD from PDX. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  


Get our best airfare deals for your flight from Portland PDX to Chicago ORD today 

If you’re flexible about when you travel, November is usually the cheapest month to fly from Portland PDX to Chicago ORD. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 


Book flexible airline tickets for flights to Chicago ORD from Portland PDX 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to ORD from PDX have this option.  


Travel with confidence when you book flights to Chicago ORD from Portland PDX with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.