Cheap Flights From O'Hare Intl. (ORD) To Portland Intl. (PDX)

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Cheapest Flights from Chicago (ORD) to Portland (PDX)

The cheapest flights to Portland Intl. found within the past 7 days were CA $302 round trip and CA $142 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 23 - Fri, Jan 30
ORD
Chicago
PDX
Portland
CA $302 Roundtrip, found 8 hours ago
CA $302
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Fri, Jan 23 from Chicago to Portland, returning Fri, Jan 30, priced at CA $302 found 8 hours ago
Fri, Jan 23 - Fri, Jan 30
ORD
Chicago
PDX
Portland
CA $316 Roundtrip, found 8 hours ago
CA $316
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Fri, Jan 23 from Chicago to Portland, returning Fri, Jan 30, priced at CA $316 found 8 hours ago
Fri, Jan 23 - Fri, Jan 30
ORD
Chicago
PDX
Portland
CA $330 Roundtrip, found 8 hours ago
CA $330
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Fri, Jan 23 from Chicago to Portland, returning Fri, Jan 30, priced at CA $330 found 8 hours ago
Wed, Nov 19 - Sat, Nov 22
ORD
Chicago
PDX
Portland
CA $330 Roundtrip, found 6 days ago
CA $330
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Wed, Nov 19 from Chicago to Portland, returning Sat, Nov 22, priced at CA $330 found 6 days ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
PDX
Portland
CA $340 Roundtrip, found 4 days ago
CA $340
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Nov 7 from Chicago to Portland, returning Tue, Nov 11, priced at CA $340 found 4 days ago
Wed, Nov 19 - Sat, Nov 22
ORD
Chicago
PDX
Portland
CA $344 Roundtrip, found 6 days ago
CA $344
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Wed, Nov 19 from Chicago to Portland, returning Sat, Nov 22, priced at CA $344 found 6 days ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
PDX
Portland
CA $354 Roundtrip, found 4 days ago
CA $354
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Nov 7 from Chicago to Portland, returning Tue, Nov 11, priced at CA $354 found 4 days ago
Fri, Jan 2 - Wed, Jan 7
ORD
Chicago
PDX
Portland
CA $366 Roundtrip, found 8 hours ago
CA $366
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Fri, Jan 2 from Chicago to Portland, returning Wed, Jan 7, priced at CA $366 found 8 hours ago
Fri, Nov 7 - Tue, Nov 11
ORD
Chicago
PDX
Portland
CA $367 Roundtrip, found 4 days ago
CA $367
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Nov 7 from Chicago to Portland, returning Tue, Nov 11, priced at CA $367 found 4 days ago
Fri, Jan 2 - Wed, Jan 7
ORD
Chicago
PDX
Portland
CA $399 Roundtrip, found 8 hours ago
CA $399
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Fri, Jan 2 from Chicago to Portland, returning Wed, Jan 7, priced at CA $399 found 8 hours ago

Frequently asked questions

Are there direct flights from ORD to PDX?
United Airlines and American Airlines are among the airlines that have direct flights from ORD to PDX. If you want to get to your destination without a stopover, be sure to check out their fares.
What airlines fly from O'Hare Intl. Airport (ORD) to PDX?
If you need to get to Portland from Chicago, you'll find a few airlines that have direct flights. One of the most reputable carriers is United Airlines (UA), which operates 152 flights on this route each month. An alternative is American Airlines (AA), which has 52 flights each month. The more airlines you weigh up, the more likely you are to pick up a wonderful deal.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca 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 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago (ORD) today with the cheap prices from Travelocity!

Popular Flight Routes from Portland (PDX)

Travelers at PDX love to visit these top cities. Roam to the top destinations from Portland(PDX) today with the cheap prices from Travelocity!

*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.