$88 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 $176 round trip and $88 one way. Prices and availability subject to change. Additional terms may apply.

Flight Schedule for PDX to ORD

CarrierFlightDepart PDXArrive ORDSun
UA191506:45 am00:41 pmCheck FareCheck FareCheck Fare
0 Stops
AS68607:00 am01:01 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops
AA184811:50 am05:47 pmCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops
UA217702:13 pm08:04 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops
UA149011:59 pm05:42 amCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops
UA169306:45 am00:41 pm
Check FareCheck FareCheck FareCheck Fare
0 Stops
UA215108:55 am06:28 pm
Check Fare
1 Stops

Best O'Hare Intl. Flight and Hotel Packages

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

Fairmont Chicago at Millennium Park
Claridge House
InterContinental Chicago Magnificent Mile, an IHG Hotel
Kimpton Gray Hotel, an IHG Hotel
Thompson Chicago
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Frequently asked questions

Can I catch a flight from PDX Airport to O'Hare Intl. Airport (ORD) right now?
It’s wise to know about any travel advice reports and quarantine requirements in effect in your destination. Be sure to go to our Covid-19 Travel Advisor for up-to-date info on catching a flight to O’Hare Intl. Airport (ORD) from Portland Airport.
Are there direct flights from Portland Intl. Airport (PDX) to O'Hare Airport?
Multiple airlines offer passengers direct flights from PDX Airport to O’Hare Airport. Among these are United Airlines and American Airlines — start with them if you’d like to land at Chicago sooner rather than later.
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 O'Hare Intl. Airport (ORD)?
The flight time between Portland Intl. Airport (PDX) and O’Hare Airport is approximately 4 hours. Make your journey more comfortable by saving a few podcasts on your tablet or laptop and enjoying them with your seat fully reclined.
What is the flight distance from PDX Airport to ORD?
Traveling 1,750 mi between PDX Airport and PDX Airport calls for a glass of Champagne and a movie-watching session. Adjust your seat, get cozy and enjoy the ride.
What airlines fly from PDX to O'Hare Intl. Airport (ORD)?
If you need to get to Chicago from Portland, you’ll find a few airlines offering direct flights. One of the most well-known is United Airlines (UA), which offers 152 flights every month. You should also browse the deals available through American Airlines (AA). Another well-known airline, it operates 52 flights monthly on the Portland to Chicago route. Be sure to compare the two airlines to walk away with the best fare.
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 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that 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 2021, 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 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.


Traveling From Portland Intl.
Traveling To O'Hare Intl.
Shortest Flight Time 7 hours 43 mins
Earliest Departure Time 6:45AM CST
Latest Departure Time 11:59PM CST
Lowest Flight Price $176

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 3 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 $176 and $238. 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 $88. 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) 43 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, February 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.