S$160 Cheap Flights from Chicago to Portland

View S$160 flight on Wed, 5 Nov, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Portland (ORD-PDX)

Prices were available within the past 7 days and start at S$160 for one-way flights and S$357 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$357 Return, found 2 days ago
S$357
Return
found 2 days ago
Select Delta flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$357 found 2 days ago
United
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$378 Return, found 2 days ago
S$378
Return
found 2 days ago
Select United flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$378 found 2 days ago
Delta
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$397 Return, found 2 days ago
S$397
Return
found 2 days ago
Select Delta flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$397 found 2 days ago
Delta
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$403 Return, found 2 days ago
S$403
Return
found 2 days ago
Select Delta flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$403 found 2 days ago
Delta
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$415 Return, found 2 days ago
S$415
Return
found 2 days ago
Select Delta flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$415 found 2 days ago
United
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$418 Return, found 2 days ago
S$418
Return
found 2 days ago
Select United flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$418 found 2 days ago
United
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$423 Return, found 2 days ago
S$423
Return
found 2 days ago
Select United flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$423 found 2 days ago
United
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$434 Return, found 2 days ago
S$434
Return
found 2 days ago
Select United flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$434 found 2 days ago
United
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$435 Return, found 2 days ago
S$435
Return
found 2 days ago
Select United flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$435 found 2 days ago
American Airlines
Mon, 6 Oct - Sat, 11 Oct
ORD
Chicago
PDX
Portland
S$461 Return, found 2 days ago
S$461
Return
found 2 days ago
Select American Airlines flight, departing Mon, 6 Oct from Chicago to Portland, returning Sat, 11 Oct, priced at S$461 found 2 days ago

Find the cheapest month to fly from Chicago (ORD) to Portland (PDX)

September is typically the cheapest month to fly

From S$134 - S$238 per traveller.

Graph displaying average flight prices per month

Chicago to Portland route information
Origin airport
O'Hare Intl.
Destination airport
Portland Intl.
Return price
S$357
Distance
2774 km
Average flight time
2 hours 27 mins

Flights from Chicago to Portland

There are several airlines that operate frequent flights from Chicago (ORD) to Portland (PDX) including

The earliest flight leaves O'Hare Intl. Airport at 08:55 and arrives at Portland Intl. Airport at 01:06. The last flight of the day departs Chicago at 23:40 and arrives at Portland at 23:14.

The flight distance from Chicago to Portland is about 2806 km, the shortest flight is 04 hours 17 minutes with United Airlines.

Expedia lets you search across the largest number of airlines and Portland flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Portland flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Portland trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Portland flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Portland with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

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$357. 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.

Explore a world of travel with Expedia

Chicago Airports

Chicago

*Available to Expedia members.