Cheap flights from Chicago (CHI) to Portland (PDX)

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Lowest round trip fares by airline from Chicago and Portland

Cheapest prices ($84 One Way, $168 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Portland

Ramada by Wyndham Portland Airport

Ramada by Wyndham Portland Airport

2.5 out of 5
6221 NE 82nd Ave, Portland, OR, 97220
Stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms and the overall ...
3.2/5 (1,000 reviews)
"I little outdated but fits the purpose."

Reviewed on Sep 11, 2022

Howard Johnson by Wyndham Portland Airport

Howard Johnson by Wyndham Portland Airport

2 out of 5
8247 Ne Sandy Blvd, Portland, OR, 97220
The price is $84 per night from Oct 9 to Oct 10
Stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms and the family amenities ...
2.8/5 (1,000 reviews)
"Older hotel, but in reasonable condition. Staff was very friendly. Only minus for us was that there was no ice available due to someone stealing copper from ice machine apparently. Not functioning."

Reviewed on Sep 1, 2022

Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

3 out of 5
7101 NE 82nd Ave, Portland, OR, 97220
The price is $104 per night from Nov 6 to Nov 7
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, a free airport shuttle, and a fitness center. Our guests praise the helpful staff and ...
3.5/5 Good! (1,600 reviews)
"Having the shuttle to the airport was fantastic!"

Reviewed on Oct 5, 2022

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Portland

Origin Chicago
Destination Portland
Number of Daily Flights 20
Earliest Flight Departure Date Oct 14
Latest Flight Departure Date Oct 15
Popular Airlines United Airlines

Cheap flights from Chicago to Portland

Chicago O’Hare International Airport (ORD) is on the far northwest side of the city of Chicago. When coming from The Loop or downtown Chicago, take the CTA or the Metra Rail. However, if coming from the suburbs, consider the Pace Suburban Bus.

Typical flight times are a little over four hours long to Portland International Airport (PDX). The TriMet connects you to the city center of Portland and places like Beaverton.

Attractions and Tips

Portland is an outdoor lover’s dream. The Columbia River Gorge National Scenic Area offers various trails throughout and opportunities to check out the Multnomah Falls; plan for the area to be incredibly windy. The International Rose Test Garden is free to tour and displays over 8,000 types of roses.

When it comes time to head inside, take the MAX train to the Lloyd Center. Shop at the Made in Oregon store or take a break and enjoy the indoor ice skating rink.

When compared to other larger cities in the region, Portland has the warmest temperatures on average as well as the most sunshine and the least amount of rain. This makes for a great destination if enjoying the outdoors is your goal. While summers are warm and winters are cold, it’s fall and spring that tend to be more unpredictable with warm and cool changes, so consider packing a range of clothing for the trip just in case.

*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.