Cheap Flight Deals From Portland (PDX) to Chicago (CHI) Starting at $54

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Portland to Chicago

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.

Fri, Sep 29 - Tue, Oct 3
PDX
Portland Intl.
MDW
Midway Intl.
$168 Roundtrip, found 4 days ago
$168
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Sep 29 from Portland Intl. to Midway Intl., returning Tue, Oct 3, priced at $168 found 4 days ago
Fri, Sep 29 - Sun, Oct 1
PDX
Portland Intl.
ORD
O'Hare Intl.
$326 Roundtrip, found 3 hours ago
$326
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Fri, Sep 29 from Portland Intl. to O'Hare Intl., returning Sun, Oct 1, priced at $326 found 3 hours ago

Airfares from $54 One Way, $123 Round Trip from Portland to Chicago

Prices starting at $123 for return flights and $54 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Nov 1 - Sat, Nov 4
PDX
Portland
ORD
Chicago
$123 Roundtrip, found 2 days ago
$123
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Nov 1 from Portland to Chicago, returning Sat, Nov 4, priced at $123 found 2 days ago
Tue, Oct 24 - Tue, Oct 31
PDX
Portland
ORD
Chicago
$126 Roundtrip, found 5 hours ago
$126
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Tue, Oct 24 from Portland to Chicago, returning Tue, Oct 31, priced at $126 found 5 hours ago
Tue, Oct 31 - Sat, Nov 4
PDX
Portland
ORD
Chicago
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Oct 31 from Portland to Chicago, returning Sat, Nov 4, priced at $138 found 2 days ago
Tue, Oct 31 - Wed, Nov 1
PDX
Portland
ORD
Chicago
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select United flight, departing Tue, Oct 31 from Portland to Chicago, returning Wed, Nov 1, priced at $138 found 6 days ago
Tue, Oct 31 - Wed, Nov 1
PDX
Portland
ORD
Chicago
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Oct 31 from Portland to Chicago, returning Wed, Nov 1, priced at $158 found 6 days ago

More About Flying To Chicago from Portland

Route Information for Flights from Portland to Chicago

Origin Airport IATA Code
PDX
Destination Airport IATA Code
CHI
Distance
1734 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, Aer Lingus, SWISS, United Airlines, Alaska Airlines, Finnair, SAS, Brussels Airlines, Malaysia Airlines, Lufthansa, British Airways
Earliest Flight Arrival
7:58PM UTC
Latest Flight Arrival
12:52PM UTC

Plan Your Trip from Portland to Chicago

Portland International Airport

Flights from Portland depart from the Portland International Airport, located at 7000 NE Airport Way. The airport is approximately 22 miles south of downtown Portland and is serviced by 13 airlines, including Delta, Air Canada, Frontier and United. Orbitz.com makes it easy to book domestic and international flights from Portland. You don't have to scour the Internet to find cheap airline tickets. Orbitz.com searches all of the flights available to get you a ticket with a low fare.

Parking and Transportation

The Portland International Airport offers long-term parking for $19 per day. If you plan to leave your car at the airport for more than 90 days, you need to make prior arrangements with the airport's parking office. You can take a taxi from downtown Portland to the airport for approximately $32, so if you plan to leave your vehicle for more than two days, taking a taxi to the airport is a cheaper option. Streetcars also run from the downtown area to the airport, and streetcar tickets cost $2.40. If you need transportation when you arrive at your destination, Orbitz.com can reserve a rental car for you.

Dining at the Airport

If you want to grab a quick meal before your flight, the Portland International Airport has a variety of restaurant choices. You can stop in Starbucks or Coffee People for a quick snack. If you want a meal, you can eat at Wendy's, Sandoval's or Pizza Schmizza. Orbitz.com does more than book flights from Portland. The website has all of the tools you need to make sure your trip goes smoothly, giving you plenty of time to eat before your flight.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Am I able to catch a flight from Portland to Chicago now?
Head to our Covid-19 Travel Advisor for the most up-to-date info on travel restrictions and quarantine requirements when getting a flight from Portland to Chicago.
Are there non-stop flights from Portland to Chicago?
Buckle up and enjoy a worry-free flight on board one of the 3 airlines that fly straight from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD). We’ve put together a list of reliable carriers to book with:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from Portland to Chicago?
The shortest flight time from Portland to Chicago is 4 hours and 35 minutes, which gives you ample time to enjoy a red wine or get absorbed in a good movie.
What airlines fly from Portland to Chicago most frequently?
Consider booking a flight with United Airlines (UA), which flies frequently along this route. This airline offers 152 flights each month between Portland, OR (PDX-Portland Intl.) and O’Hare Airport. Also check out the great fares from American Airlines (AA). Offering 52 flights every month between Portland and Chicago, they make the journey just as delightful as the destination.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?
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 Chicago 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 Chicago with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago 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 2021 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 from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. 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.