
Be in the know
Get alerts if flight prices drop or rise*
Book smarter
Save up to 30% on select hotels after you book a flight*
$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 13 hours ago
$100
Roundtrip
found 13 hours ago

Sat, Jan 17 - Tue, Jan 20
DEN
Denver
MDW
Chicago
$109 Roundtrip, found 13 hours ago
$109
Roundtrip
found 13 hours ago

Fri, Feb 13 - Sat, Feb 14
DEN
Denver
MDW
Chicago
$121 Roundtrip, found 1 hour ago
$121
Roundtrip
found 1 hour ago

Mon, Jan 12 - Thu, Jan 15
DEN
Denver
MDW
Chicago
$128 Roundtrip, found 14 hours ago
$128
Roundtrip
found 14 hours ago

Sat, Jan 17 - Tue, Jan 20
DEN
Denver
MDW
Chicago
$130 Roundtrip, found 13 hours ago
$130
Roundtrip
found 13 hours ago

Sat, Jan 17 - Tue, Jan 20
DEN
Denver
MDW
Chicago
$133 Roundtrip, found 13 hours ago
$133
Roundtrip
found 13 hours ago
Travel information
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 18 mins |
*Available to One Key members.