
Popular airlines from Portland to Historic Route 66
Jetstar
Qantas Airways
Virgin Australia
Scoot
American Airlines
Emirates
United
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Cheap Flights from Portland (PDX) to Historic Route 66 (CHI)
Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, 21 Aug. - Thu, 28 Aug.
PDX
Portland
ORD
Chicago
AU$335 Return, found 6 days ago
AU$335
Return
found 6 days ago

Thu, 21 Aug. - Thu, 28 Aug.
PDX
Portland
ORD
Chicago
AU$336 Return, found 6 days ago
AU$336
Return
found 6 days ago

Sat, 27 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$344 Return, found 13 hours ago
AU$344
Return
found 13 hours ago

Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$345 Return, found 13 hours ago
AU$345
Return
found 13 hours ago

Thu, 21 Aug. - Thu, 28 Aug.
PDX
Portland
ORD
Chicago
AU$351 Return, found 6 days ago
AU$351
Return
found 6 days ago

Wed, 24 Sep. - Tue, 30 Sep.
PDX
Portland
ORD
Chicago
AU$481 Return, found 13 hours ago
AU$481
Return
found 13 hours ago
Find the cheapest month to fly from Portland (PDX) to Chicago (ORD)
August is typically the cheapest month to fly
From AU$135 - AU$295 per traveller.
Graph displaying average flight prices per month
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