Flights to Seaside from Chicago - $90

View $90 flight on Sat, Aug 30, 2025Opens in a new window

Popular airlines from Chicago to Seaside

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Cheap Flights from Chicago to Seaside (CHI-PDX)

Prices were available within the past 7 days and start at $90 for one-way flights and $171 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Aug 19 - Sat, Aug 30
ORD
Chicago
PDX
Portland
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Portland, returning Sat, Aug 30, priced at $171 found 1 day ago
Spirit Airlines
Tue, Aug 19 - Thu, Aug 21
ORD
Chicago
PDX
Portland
$176 Roundtrip, found 20 hours ago
$176
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Aug 19 from Chicago to Portland, returning Thu, Aug 21, priced at $176 found 20 hours ago
Southwest Airlines
Sat, Aug 30 - Sun, Aug 31
MDW
Chicago
PDX
Portland
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Chicago to Portland, returning Sun, Aug 31, priced at $179 found 6 hours ago
Alaska Airlines
Sat, Aug 30 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select Alaska Airlines flight, departing Sat, Aug 30 from Chicago to Portland, returning Sun, Aug 31, priced at $179 found 6 hours ago
United
Sat, Aug 30 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Aug 30 from Chicago to Portland, returning Sun, Aug 31, priced at $179 found 6 hours ago
American Airlines
Sat, Aug 30 - Sun, Aug 31
ORD
Chicago
PDX
Portland
$179 Roundtrip, found 6 hours ago
$179
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Chicago to Portland, returning Sun, Aug 31, priced at $179 found 6 hours ago

Find the cheapest month to fly from Chicago (CHI) to Portland (PDX)

August is typically the cheapest month to fly

From $98 - $225 per traveler.

Graph displaying average flight prices per month

*Available to One Key members.