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 $345 round trip and CA $167 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 16 - Sat, Jan 24
ORD
Chicago
PDX
Portland
CA $345 Roundtrip, found 4 days ago
CA $345
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Jan 16 from Chicago to Portland, returning Sat, Jan 24, priced at CA $345 found 4 days ago
Wed, Dec 31 - Wed, Jan 7
ORD
Chicago
PDX
Portland
CA $350 Roundtrip, found 6 days ago
CA $350
Roundtrip
found 6 days ago
Select Sun Country Airlines flight, departing Wed, Dec 31 from Chicago to Portland, returning Wed, Jan 7, priced at CA $350 found 6 days ago
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
CA $364 Roundtrip, found 3 days ago
CA $364
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at CA $364 found 3 days ago
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
CA $365 Roundtrip, found 3 days ago
CA $365
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at CA $365 found 3 days ago
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
CA $373 Roundtrip, found 3 days ago
CA $373
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at CA $373 found 3 days ago
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
CA $379 Roundtrip, found 3 days ago
CA $379
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at CA $379 found 3 days ago
Fri, Jan 16 - Sat, Jan 24
ORD
Chicago
PDX
Portland
CA $381 Roundtrip, found 4 days ago
CA $381
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Jan 16 from Chicago to Portland, returning Sat, Jan 24, priced at CA $381 found 4 days ago
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
CA $387 Roundtrip, found 3 days ago
CA $387
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at CA $387 found 3 days ago
Thu, Dec 4 - Thu, Dec 11
ORD
Chicago
PDX
Portland
CA $402 Roundtrip, found 3 days ago
CA $402
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 4 from Chicago to Portland, returning Thu, Dec 11, priced at CA $402 found 3 days ago
Wed, Dec 31 - Wed, Jan 7
ORD
Chicago
PDX
Portland
CA $404 Roundtrip, found 6 days ago
CA $404
Roundtrip
found 6 days ago
Select Sun Country Airlines flight, departing Wed, Dec 31 from Chicago to Portland, returning Wed, Jan 7, priced at CA $404 found 6 days 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.