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Chicago skyline
MDW
Chicago
Portland Maine skyline at sunset
PWM
Portland

Chicago → Portland

Southwest Airlines · Round Trip · Nonstop

$498

per person · round trip

Book This Deal

Flight Details

Cabin
Economy
Departs
Aug 15, 2026
Returns
Aug 21, 2026

Price History

Avg: $495
Low: $491
High: $498
$480$487$493$500Apr 2Apr 3

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