$59 Cheap Southwest Airlines flights Denver (DEN) to Chicago (MDW)

View $59 flight on Wed, Sep 17, 2025Opens in a new window

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$59 Cheap Southwest Airlines flights Denver (DEN) to Chicago (MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $118 for roundtrip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Southwest Airlines
Wed, Sep 17 - Wed, Sep 24
DEN
Denver
MDW
Chicago
$118
Roundtrip
Just found
Select Southwest Airlines flight, departing Wed, Sep 17 from Denver to Chicago, returning Wed, Sep 24, priced at $118 Just found
Southwest Airlines
Sat, Sep 13 - Tue, Sep 16
DEN
Denver
MDW
Chicago
$127
Roundtrip
Found 10 hours ago
Select Southwest Airlines flight, departing Sat, Sep 13 from Denver to Chicago, returning Tue, Sep 16, priced at $127 Found 10 hours ago
Southwest Airlines
Wed, Sep 17 - Wed, Sep 24
DEN
Denver
MDW
Chicago
$128
Roundtrip
Just found
Select Southwest Airlines flight, departing Wed, Sep 17 from Denver to Chicago, returning Wed, Sep 24, priced at $128 Just found
Southwest Airlines
Wed, Sep 17 - Wed, Sep 24
DEN
Denver
MDW
Chicago
$133
Roundtrip
Just found
Select Southwest Airlines flight, departing Wed, Sep 17 from Denver to Chicago, returning Wed, Sep 24, priced at $133 Just found
Southwest Airlines
Sat, Sep 13 - Sat, Sep 27
DEN
Denver
MDW
Chicago
$136
Roundtrip
Found 13 hours ago
Select Southwest Airlines flight, departing Sat, Sep 13 from Denver to Chicago, returning Sat, Sep 27, priced at $136 Found 13 hours ago
Southwest Airlines
Sat, Sep 13 - Tue, Sep 16
DEN
Denver
MDW
Chicago
$137
Roundtrip
Found 10 hours ago
Select Southwest Airlines flight, departing Sat, Sep 13 from Denver to Chicago, returning Tue, Sep 16, priced at $137 Found 10 hours ago
Flights from Denver (DEN) to Chicago (MDW)
Origin airport
Denver Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Popular airline
Frontier Airlines
Distance
893 mi
Average flight time
3 hours 22 mins

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