S$237 Cheap Flights from Chicago to Portland

View S$237 flight on Fri, 22 May, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Portland International Airport (PDX)

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Cheap Flights from Chicago to Portland (ORD-PDX)

Prices were available within the past 7 days and start at S$237 for one-way flights and S$459 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$459 Return, found 4 days ago
S$459
Return
found 4 days ago
Select Delta flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$459 found 4 days ago
American Airlines
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$493 Return, found 4 days ago
S$493
Return
found 4 days ago
Select American Airlines flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$493 found 4 days ago
Delta
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$507 Return, found 4 days ago
S$507
Return
found 4 days ago
Select Delta flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$507 found 4 days ago
United
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$512 Return, found 4 days ago
S$512
Return
found 4 days ago
Select United flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$512 found 4 days ago
American Airlines
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$519 Return, found 4 days ago
S$519
Return
found 4 days ago
Select American Airlines flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$519 found 4 days ago
American Airlines
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$524 Return, found 4 days ago
S$524
Return
found 4 days ago
Select American Airlines flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$524 found 4 days ago
Delta
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$526 Return, found 4 days ago
S$526
Return
found 4 days ago
Select Delta flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$526 found 4 days ago
American Airlines
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$538 Return, found 4 days ago
S$538
Return
found 4 days ago
Select American Airlines flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$538 found 4 days ago
Delta
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$540 Return, found 4 days ago
S$540
Return
found 4 days ago
Select Delta flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$540 found 4 days ago
Delta
Fri, 22 May - Fri, 29 May
ORD
Chicago
PDX
Portland
S$543 Return, found 4 days ago
S$543
Return
found 4 days ago
Select Delta flight, departing Fri, 22 May from Chicago to Portland, returning Fri, 29 May, priced at S$543 found 4 days ago

Frequently asked questions

How much is a flight from ORD to PDX?
If you're travelling from O'Hare Intl. Airport (ORD) to PDX, round-trip flights start from S$459. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year, so don't let a good deal slip through your fingers. Book today and save yourself both money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from O'Hare Intl. Airport (ORD) to PDX Airport?
Each air carrier has its own terms and conditions. If you do decide to cancel, follow the instructions on our Customer Service Portal.
How do I find cheap flights from O'Hare Intl. Airport (ORD) to PDX that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for ORD to Portland Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to Portland Intl. Airport (PDX)?
You'll be in the air for a while, as the flight distance from O'Hare Intl. Airport (ORD) to Portland Airport is 2,800 kilometres. Create a playlist of your favourite songs before you leave home to keep yourself entertained during your flight.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to PDX?
United Airlines (UA) is a top choice. It offers 86 flights from O'Hare Airport to Portland Intl. Airport (PDX) each month. If you want more options, check out the ticket prices from Alaska Airlines (AS). This airlines operates 30 flights every month between these airports.
Are O'Hare Intl. Airport (ORD) to PDX Airport flight tickets cheaper when they're purchased at the last minute?
Airline tickets from ORD to Portland Airport are available up to a year prior to departure on Expedia. And although you may nab a fantastic last-minute deal, it's not something you should bank on. Also, booking your flights in advance means you'll have more options — and you can avoid ending up with the dreaded middle seat! We regularly update our fares to bring you the best bargains, so keep checking in for all the latest specials.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Portland Intl.
Return price
S$459
Distance
2774 km
Average flight time
2 hours 33 mins

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