$50 Cheap Southwest Airlines flights Denver (DEN) to Chicago (MDW)

$50 Cheap Southwest Airlines flights Denver (DEN) to Chicago (MDW)

Prices were available within the past 7 days and start at $50 for one-way flights and $100 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 17 - Tue, Jan 20

DEN

Denver

MDW

Chicago

$100 Roundtrip, found 17 hours ago

$100

Roundtrip

found 17 hours ago

Select Southwest Airlines flight, departing Sat, Jan 17 from Denver to Chicago, returning Tue, Jan 20, priced at $100 found 17 hours ago

Tue, Dec 30 - Fri, Jan 9

DEN

Denver

MDW

Chicago

$108 Roundtrip, found 1 hour ago

$108

Roundtrip

found 1 hour ago

Select Southwest Airlines flight, departing Tue, Dec 30 from Denver to Chicago, returning Fri, Jan 9, priced at $108 found 1 hour ago

Sat, Jan 17 - Tue, Jan 20

DEN

Denver

MDW

Chicago

$109 Roundtrip, found 17 hours ago

$109

Roundtrip

found 17 hours ago

Select Southwest Airlines flight, departing Sat, Jan 17 from Denver to Chicago, returning Tue, Jan 20, priced at $109 found 17 hours ago

Wed, Dec 17 - Sun, Jan 18

DEN

Denver

MDW

Chicago

$113 Roundtrip, just found

$113

Roundtrip

just found

Select Southwest Airlines flight, departing Wed, Dec 17 from Denver to Chicago, returning Sun, Jan 18, priced at $113 just found

Wed, Dec 17 - Sun, Jan 18

DEN

Denver

MDW

Chicago

$118 Roundtrip, just found

$118

Roundtrip

just found

Select Southwest Airlines flight, departing Wed, Dec 17 from Denver to Chicago, returning Sun, Jan 18, priced at $118 just found

Fri, Feb 13 - Sat, Feb 14

DEN

Denver

MDW

Chicago

$121 Roundtrip, found 5 hours ago

$121

Roundtrip

found 5 hours ago

Select Southwest Airlines flight, departing Fri, Feb 13 from Denver to Chicago, returning Sat, Feb 14, priced at $121 found 5 hours ago