Cheapest flights from Chicago
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Apr 4 - Wed, Apr 10
ORD
O'Hare Intl.
PDX
Portland Intl.
$209 Roundtrip, found 17 hours ago
$209
Roundtrip
found 17 hours ago
Wed, Apr 3 - Wed, Apr 10
ORD
O'Hare Intl.
PDX
Portland Intl.
$214 Roundtrip, found 17 hours ago
$214
Roundtrip
found 17 hours ago
Thu, Apr 4 - Tue, Apr 9
ORD
O'Hare Intl.
PDX
Portland Intl.
$228 Roundtrip, found 17 hours ago
$228
Roundtrip
found 17 hours ago
Wed, Apr 3 - Tue, Apr 9
ORD
O'Hare Intl.
PDX
Portland Intl.
$233 Roundtrip, found 17 hours ago
$233
Roundtrip
found 17 hours ago
Thu, Jun 6 - Mon, Jun 17
MDW
Midway Intl.
PDX
Portland Intl.
$245 Roundtrip, found 3 days ago
$245
Roundtrip
found 3 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$262 Roundtrip, found 3 days ago
$262
Roundtrip
found 3 days ago
Tue, Apr 2 - Wed, Apr 10
ORD
O'Hare Intl.
PDX
Portland Intl.
$279 Roundtrip, found 17 hours ago
$279
Roundtrip
found 17 hours ago
Tue, Apr 2 - Tue, Apr 9
ORD
O'Hare Intl.
PDX
Portland Intl.
$298 Roundtrip, found 17 hours ago
$298
Roundtrip
found 17 hours ago
Thu, Jun 6 - Tue, Jun 18
MDW
Midway Intl.
PDX
Portland Intl.
$304 Roundtrip, found 3 days ago
$304
Roundtrip
found 3 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$305 Roundtrip, found 3 days ago
$305
Roundtrip
found 3 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$316 Roundtrip, found 3 days ago
$316
Roundtrip
found 3 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$317 Roundtrip, found 3 days ago
$317
Roundtrip
found 3 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$327 Roundtrip, found 3 days ago
$327
Roundtrip
found 3 days ago
Sun, Mar 31 - Wed, Apr 10
ORD
O'Hare Intl.
PDX
Portland Intl.
$339 Roundtrip, found 17 hours ago
$339
Roundtrip
found 17 hours ago
Sun, Mar 31 - Tue, Apr 9
ORD
O'Hare Intl.
PDX
Portland Intl.
$358 Roundtrip, found 17 hours ago
$358
Roundtrip
found 17 hours ago
Fri, Sep 13 - Tue, Sep 17
ORD
O'Hare Intl.
PDX
Portland Intl.
$360 Roundtrip, found 6 days ago
$360
Roundtrip
found 6 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$365 Roundtrip, found 3 days ago
$365
Roundtrip
found 3 days ago
Fri, Sep 13 - Tue, Sep 17
ORD
O'Hare Intl.
PDX
Portland Intl.
$365 Roundtrip, found 6 days ago
$365
Roundtrip
found 6 days ago
Tue, Jun 11 - Sat, Jun 15
ORD
O'Hare Intl.
PDX
Portland Intl.
$369 Roundtrip, found 3 days ago
$369
Roundtrip
found 3 days ago
Sat, Jul 13 - Sat, Jul 20
ORD
O'Hare Intl.
PDX
Portland Intl.
$432 Roundtrip, found 3 days ago
$432
Roundtrip
found 3 days ago