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Lowest round trip fares by airline from Chicago and Portland

Cheapest prices ($64 One Way, $120 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
The price is $89 per night from Oct 21 to Oct 21
Situated near the airport, this hotel is 2 mi (3.2 km) from Cascade Station and within 6 mi (10 km) of Alberta Street and Concordia University. Woodlawn Park ...
3.4/5 (11 reviews)
"The bldg. Is old; it smelled moldy, like a cabin you hadn’t been to in years. It’s needs updating."

Reviewed on Dec 14, 2019

Ramada by Wyndham Portland Airport
Howard Johnson by Wyndham Portland Airport

Howard Johnson by Wyndham Portland Airport

2 out of 5
8247 Ne Sandy Blvd, Portland, OR
The price is $69 per night from Oct 31 to Oct 31
Situated near the airport, this hotel is within 3 mi (5 km) of Cascade Station, Providence Portland Medical Center, and Alberta Street. Mall 205 and Laurelhurst ...
2.9/5 (7 reviews)
"No warm water at times. Microwave with no connection extension. Hotel beat up. Staff not too friendly."

Reviewed on Feb 25, 2020

Howard Johnson by Wyndham Portland Airport
Red Lion Hotel Portland Airport

Red Lion Hotel Portland Airport

3 out of 5
7101 NE 82nd Ave, Portland, OR
The price is $88 per night from Nov 3 to Nov 3
Situated near the airport, this hotel is 1.6 mi (2.5 km) from Cascade Station and 3.1 mi (5 km) from Columbia River. Alberta Street and Alberta Rose Theatre ...
4.7/5 Exceptional! (10 reviews)
"The room was dirty. It looked like someone spit on the walls in the bathroom shower, as well on the bathroom light bar. There was a smeared nose fluid on the light switch. The security latch was broken and unusable. Body fluid stains on the chair. That was just a few things, there was a lot more"

Reviewed on Apr 16, 2021

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.

Flights Review

Aug 29, 2018

I flew United to Chicago and American Airlines back for a short weekend business trip this last week. I’ll always choose American now! The staff was amazing on American and the seats were even more spacious. I felt like a guest versus a number on American.

A verified traveler
Chicago to Portland · American Airlines
Apr 6, 2018

Not really. I was well satisfied. Thanks;

A verified traveler
Chicago to Portland · American Airlines

Fly From Chicago to Portland

Origin Chicago
Destination Portland
Number of Daily Flights 25
Earliest Flight Departure Date Oct 27
Latest Flight Departure Date Oct 28
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.