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Lowest round trip fares by airline from Chicago and Portland

Cheapest prices ($46 One Way, $91 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
2.5 out of 5.0
2.9 out of 5 (22 reviews)

Situated near the airport, this hotel is 1.5 mi (2.5 km) from Grotto and 2 mi (3.2 km) from Cascade Station. Concordia University and Grant Park are also within ...

The bldg. Is old; it smelled moldy, like a cabin you hadn’t been to in years. It’s needs updating.
  
Howard Johnson by Wyndham Portland Airport
2.0 out of 5.0
2.8 out of 5 (12 reviews)

Situated near the airport, this hotel is within 3 mi (5 km) of Grotto, Cascade Station, and Grant Park. Providence Portland Medical Center is 3 mi (4.8 km) away. ...

Nothing extrordinary. It is what it says it is and was a nice hotel to stay at. Breakfast was very basic, not much to choose from. But clean healthy and edible.
  
Red Lion Hotel Portland Airport
3.0 out of 5.0
3.7 out of 5 (17 reviews)

Situated near the airport, this hotel is 1.6 mi (2.5 km) from Cascade Station and 2 mi (3.1 km) from Grotto. Concordia University and Grant Park are also within ...

The restaurant on the facility was awesome. The shuttle service to and from the Airport was super handy.
  

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.

Apr 6, 2018

Not really. I was well satisfied. Thanks;

Fly From Chicago to Portland

OriginChicago
DestinationPortland
Number of Daily Flights3
Earliest Flight Departure DateAug 19
Latest Flight Departure DateAug 19
Popular AirlinesAlaska Airlines

Cheap flights from Chicago to Portland

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.