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

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Lowest round trip fares by airline from Portland and Chicago

Cheapest prices ($129 One Way, $258 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

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL, 60611
The price is $116 per night from Jul 5 to Jul 6
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
3.9/5 Good! (9 reviews)
"I really appreciated the staff there. Thanks"

Reviewed on Oct 16, 2021

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL, 60605
The price is $159 per night from Jul 5 to Jul 6
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and onsite parking. Our guests praise the breakfast and the restaurant in our reviews. ...
3.3/5 (7 reviews)
"Location was good. The curtains weren't great. Room was very bright. They bathtub was broken and wouldn't hold water. Couldn't take a bath which was the reason we chose this hotel."

Reviewed on Jun 19, 2022

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL, 60007
The price is $60 per night from Jul 6 to Jul 7
Stay at this business-friendly motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
4.2/5 Very Good! (11 reviews)
"This was a very great bang for your buck! Clean and Quiet"

Reviewed on Sep 11, 2021

Motel 6 Elk Grove Village, IL - O'Hare
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 Portland to Chicago

Origin Portland
Destination Chicago
Number of Daily Flights 25
Earliest Flight Departure Date Jul 7
Latest Flight Departure Date Jul 8
Popular Airlines American Airlines

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.