Woven Adventures

Flights from Portland to Chicago

7 deals on this route

Chicago skyline and Lake Michigan
Save 52%
$158
$326
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
Frontier Airlines
Nonstop·round trip
Apr 27 – Apr 30
Chicago skyline and Lake Michigan
$321
$326
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
Frontier Airlines
Nonstop·round trip
Jun 11 – Jun 15
Chicago skyline and Lake Michigan
$326
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
Alaska Airlines
Nonstop·round trip
Jun 15 – Jun 19
Chicago skyline and Lake Michigan
$326
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
American Airlines
Nonstop·round trip
Jun 12 – Jun 15
Chicago skyline and Lake Michigan
$326
$334
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
Southwest Airlines
Nonstop·round trip
Jun 12 – Jun 16
Chicago skyline and Lake Michigan
$327
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
Alaska Airlines
Nonstop·round trip
Jun 12 – Jun 15
Chicago skyline and Lake Michigan
$337
Portland skyline with Mount Hood
PDXCHI
Portland to Chicago
American Airlines
Nonstop·round trip
Jun 14 – Jun 19