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Lowest round trip fares by airline from Chicago and Portland

Cheapest prices ($55 One Way, $109 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
Stay at this hotel in Portland. Enjoy free WiFi, a 24-hour front desk, and a 24-hour business center. Popular attractions Moda Center and Lloyd Center are located ...
6.4/10 (1,000 reviews)
"The hotel was closed although we booked it through Expedia. Was unable to stay there"

Reviewed on Sep 18, 2022

Ramada by Wyndham Portland Airport
Quality Inn Portland Airport PDX

Quality Inn Portland Airport PDX

2 out of 5
8247 Ne Sandy Blvd, Portland, OR
The price is $75 per night from Apr 21 to Apr 22
$75
per night
Apr 21 - Apr 22
Stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
6.4/10 (124 reviews)
"I like not domuch noisy"

Reviewed on Mar 22, 2024

Quality Inn Portland Airport PDX
Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

3 out of 5
7101 NE 82nd Ave, Portland, OR
The price is $85 per night from Apr 23 to Apr 24
$85
per night
Apr 23 - Apr 24
Stay at this business-friendly hotel in Portland. Enjoy free WiFi, a free airport shuttle, and a fitness center. Our guests praise the helpful staff and the ...
7/10 Good! (1,999 reviews)
Helpful staff! Sound carries...
"My stay was very short, as I checked in about midnight, and requested a 5:40 AM shuttle ride to the airport. I was zipping up my luggage the next morning, and the front desk called to confirm I was still needing the shuttle as I was about to miss it. My one complaint results from other folks staying ..."

Reviewed on Apr 18, 2024

Red Lion Hotel Portland Airport
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
15
Earliest Flight Departure Date
Apr 26
Latest Flight Departure Date
Apr 27
Popular Airlines
Alaska 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.