Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

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

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Lowest round trip fares by airline from Portland and Chicago

Cheapest prices ($104 One Way, $187 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Aug 24
PDX
Portland
ORD
Chicago
$104
Frontier Airlines
Tue, Aug 31
PDX
Portland
ORD
Chicago
$109
Frontier Airlines
Tue, Oct 12
PDX
Portland
ORD
Chicago
$119
Alaska Airlines
Wed, Nov 3
PDX
Portland
MDW
Chicago
$128
Delta
Tue, Sep 14
PDX
Portland
ORD
Chicago
$128
Delta
Tue, Aug 3 - Sat, Aug 14
PDX
Portland
ORD
Chicago
$187
Frontier Airlines
Tue, Aug 3 - Sat, Sep 11
PDX
Portland
ORD
Chicago
$209
Frontier Airlines
Tue, Aug 17 - Fri, Aug 20
PDX
Portland
ORD
Chicago
$217
Frontier Airlines
Tue, Aug 3 - Sat, Sep 11
PDX
Portland
ORD
Chicago
$228
Frontier Airlines
Tue, Sep 28 - Sat, Oct 2
PDX
Portland
ORD
Chicago
$237
United

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $101 per night from Jul 1 to Jul 1
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 ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $116 per night from Jun 27 to Jun 27
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 ...
3/5 (10 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

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
The price is $45 per night from Jul 6 to Jul 6
Situated in Elk Grove Village, this motel 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.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 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.

Flights Review

Fly From Portland to Chicago

Origin Portland
Destination Chicago
Number of Daily Flights 25
Earliest Flight Departure Date Jul 2
Latest Flight Departure Date Jul 3
Popular Airlines Alaska 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.