Cheapest flights from Portland
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.
Fri, May 17 - Wed, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$136 Roundtrip, found 2 hours ago
$136
Roundtrip
found 2 hours ago
Mon, May 13 - Wed, May 22
PDX
Portland Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Sun, May 12 - Wed, May 22
PDX
Portland Intl.
ORD
O'Hare Intl.
$165 Roundtrip, found 5 days ago
$165
Roundtrip
found 5 days ago
Mon, May 13 - Wed, May 22
PDX
Portland Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 5 days ago
$181
Roundtrip
found 5 days ago
Fri, May 17 - Wed, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$184 Roundtrip, found 2 hours ago
$184
Roundtrip
found 2 hours ago
Sun, May 26 - Wed, Jun 5
PDX
Portland Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Mon, May 13 - Tue, May 21
PDX
Portland Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Fri, May 31 - Sat, Jun 8
PDX
Portland Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Fri, May 31 - Sat, Jun 8
PDX
Portland Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Fri, May 17 - Wed, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$198 Roundtrip, found 2 hours ago
$198
Roundtrip
found 2 hours ago
Fri, May 17 - Wed, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 2 hours ago
$199
Roundtrip
found 2 hours ago
Mon, May 13 - Mon, May 27
PDX
Portland Intl.
ORD
O'Hare Intl.
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Sun, May 26 - Wed, Jun 5
PDX
Portland Intl.
ORD
O'Hare Intl.
$201 Roundtrip, found 5 days ago
$201
Roundtrip
found 5 days ago
Sat, May 18 - Tue, May 21
PDX
Portland Intl.
ORD
O'Hare Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Fri, May 17 - Wed, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Thu, Jun 13 - Fri, Jun 21
PDX
Portland Intl.
ORD
O'Hare Intl.
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
Mon, May 13 - Wed, May 22
PDX
Portland Intl.
ORD
O'Hare Intl.
$211 Roundtrip, found 5 days ago
$211
Roundtrip
found 5 days ago
Fri, May 17 - Thu, May 30
PDX
Portland Intl.
MDW
Midway Intl.
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Thu, Jul 11 - Fri, Jul 12
PDX
Portland Intl.
ORD
O'Hare Intl.
$228 Roundtrip, found 5 days ago
$228
Roundtrip
found 5 days ago
Fri, May 17 - Wed, May 29
PDX
Portland Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago