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Lowest round trip fares by airline from Portland and Chicago

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 Chicago

Freehand Chicago
3.5 out of 5.0
4.4 out of 5 (14 reviews)

Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

I didn’t like that there wasn’t a little fridge in every room or there wasn’t a coffee pot or a glass for water.
Travelodge by Wyndham Downtown Chicago
2.0 out of 5.0
3.5 out of 5 (8 reviews)

Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...

It was an excellent location close to everything. Staff kind and very helpful. Great experience
Motel 6 Elk Grove Village, IL - O'Hare
2.0 out of 5.0
3.6 out of 5 (15 reviews)

Situated in Elk Grove Village, this hotel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.

It was clean, staff was nice and attentive. Close to airport. walls are not the thickest but not paper thin. felt save with covid protocalls.

Flights Review

Jun 20, 2019

Went economy so had to check both bags, so if you add that it probably would have cost the same. Will no next time. Not bad. Just a observation

Nov 23, 2018

Elva who checked us in with Alaskan airlines at PDX was amazing !

Nov 12, 2018

Everyone was really nice

Oct 30, 2018


Apr 15, 2018

I had booked the wrong day and United did an amazing job at getting me to where I was supposed to be

Mar 22, 2018

I reserved an on board lunch which was sold out by the time the steward got to my row. At check in my flight miles was added to my american advantage program.

Fly From Portland to Chicago

Number of Daily Flights9
Earliest Flight Departure DateAug 18
Latest Flight Departure DateAug 18
Popular AirlinesAlaska Airlines

Cheap flights from Portland to Chicago

Cheap flights from Portland to Chicago

Whether traveling for a business meeting or vacation, as you arrive in Chicago from Portland, get ready to experience the day-and-night action of this busy city. Chicago's O'Hare International Airport is active 24 hours a day, so you'll want to have your rental car reserved and waiting for you. After you collect your luggage, you could stretch your legs at Woodfield Mall, or head over to the shores of Lake Michigan for a leisurely stroll.

Key Facts

Sports fans could pay a visit to the Wrigleyville if the Cubs are playing. You'll find plenty of Chicago-style hot dogs and pizza from street vendors to fill you up. From there, take one of the local streets east to connect to Lake Shore Drive. Drive south until you reach Museum Campus, which features attractions including the Field Museum of Natural History, the Shedd Aquarium and the Addler Planetarium.

Hints and Tips

Your trip from Portland International Airport (PDX) to O'Hare International Airport (ORD) should take about three hours. From ORD, it's a short drive to the downtown area where you can catch a game of the Bulls or Blackhawks. Afterward, visit the iconic Buckingham Fountain, which is located in Grant Park. There is plenty of space at the park to take a jog or have a picnic, between visiting Chicago's attractions.

*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.