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

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Lowest round trip fares by airline from Portland and Chicago

Cheapest prices ($63 One Way, $165 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 14 - Fri, Jan 16
PDX
Portland
ORD
Chicago
$165 Roundtrip, found 13 hours ago
$165
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Jan 14 from Portland to Chicago, returning Fri, Jan 16, priced at $165 found 13 hours ago
Thu, Jan 15 - Sat, Jan 17
PDX
Portland
RFD
Rockford
$165 Roundtrip, found 13 hours ago
$165
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Thu, Jan 15 from Portland to Rockford, returning Sat, Jan 17, priced at $165 found 13 hours ago
Wed, Jan 14 - Fri, Jan 16
PDX
Portland
ORD
Chicago
$165 Roundtrip, found 13 hours ago
$165
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Jan 14 from Portland to Chicago, returning Fri, Jan 16, priced at $165 found 13 hours ago
Wed, Jan 14 - Fri, Jan 16
PDX
Portland
RFD
Rockford
$172 Roundtrip, found 13 hours ago
$172
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Jan 14 from Portland to Rockford, returning Fri, Jan 16, priced at $172 found 13 hours ago
Thu, Jan 15 - Sat, Jan 17
PDX
Portland
ORD
Chicago
$180 Roundtrip, found 13 hours ago
$180
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Jan 15 from Portland to Chicago, returning Sat, Jan 17, priced at $180 found 13 hours ago

Fly From Portland to Chicago

Origin
Portland
Destination
Chicago
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular 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.

Flights from Cities near Portland

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*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.