
Popular airlines from Portland International Airport (PDX) to Chicago Midway Airport (MDW)
- Southwest Airlines
Southwest Airlines
- Delta
Delta
- Frontier Airlines
Frontier Airlines
- Plan, book, fly with confidence
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Cheap Flights from Portland to Chicago (PDX-MDW)
Prices were available within the past 7 days and start at $62 for one-way flights and $105 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$105 Roundtrip, found 14 hours ago
$105
Roundtrip
found 14 hours ago

Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$115 Roundtrip, found 14 hours ago
$115
Roundtrip
found 14 hours ago

Tue, Aug 19 - Sat, Aug 30
PDX
Portland
MDW
Chicago
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago

Fri, Sep 19 - Sat, Sep 27
PDX
Portland
MDW
Chicago
$119 Roundtrip, found 13 hours ago
$119
Roundtrip
found 13 hours ago

Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$120 Roundtrip, found 14 hours ago
$120
Roundtrip
found 14 hours ago

Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$124 Roundtrip, found 14 hours ago
$124
Roundtrip
found 14 hours ago

Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$125 Roundtrip, found 14 hours ago
$125
Roundtrip
found 14 hours ago

Tue, Aug 19 - Sat, Aug 30
PDX
Portland
MDW
Chicago
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago

Tue, Oct 21 - Wed, Nov 12
PDX
Portland
MDW
Chicago
$151 Roundtrip, found 15 hours ago
$151
Roundtrip
found 15 hours ago

Sun, Sep 21 - Fri, Sep 26
PDX
Portland
MDW
Chicago
$275 Roundtrip, found 20 hours ago
$275
Roundtrip
found 20 hours ago
Find the cheapest month to fly from Portland (PDX) to Chicago (MDW)
October is typically the cheapest month to fly
From $118 - $443 per traveler.
Graph displaying average flight prices per month
Origin airport | Portland Intl. |
Destination airport | Midway Intl. |
Airlines serving | Delta, Frontier Airlines, Southwest Airlines |
Roundtrip price | $105 |
Distance | 1746 mi |
Average flight time | 7 hours 17 mins |
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