$59 Cheap Southwest Airlines flights Orlando (MCO) to Chicago (MDW)

$59 Cheap Southwest Airlines flights Orlando (MCO) to Chicago (MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $98 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Feb 5 - Mon, Feb 9

MCO

Orlando

MDW

Chicago

$98 Roundtrip, found 2 hours ago

$98

Roundtrip

found 2 hours ago

Select Southwest Airlines flight, departing Thu, Feb 5 from Orlando to Chicago, returning Mon, Feb 9, priced at $98 found 2 hours ago

Thu, Feb 5 - Mon, Feb 9

MCO

Orlando

MDW

Chicago

$104 Roundtrip, found 2 hours ago

$104

Roundtrip

found 2 hours ago

Select Southwest Airlines flight, departing Thu, Feb 5 from Orlando to Chicago, returning Mon, Feb 9, priced at $104 found 2 hours ago

Thu, Feb 5 - Mon, Feb 9

MCO

Orlando

MDW

Chicago

$107 Roundtrip, found 2 hours ago

$107

Roundtrip

found 2 hours ago

Select Southwest Airlines flight, departing Thu, Feb 5 from Orlando to Chicago, returning Mon, Feb 9, priced at $107 found 2 hours ago

Wed, Jan 28 - Fri, Jan 30

MCO

Orlando

MDW

Chicago

$108 Roundtrip, found 3 hours ago

$108

Roundtrip

found 3 hours ago

Select Southwest Airlines flight, departing Wed, Jan 28 from Orlando to Chicago, returning Fri, Jan 30, priced at $108 found 3 hours ago

Fri, Dec 12 - Sun, Jan 11

MCO

Orlando

MDW

Chicago

$114 Roundtrip, just found

$114

Roundtrip

just found

Select Southwest Airlines flight, departing Fri, Dec 12 from Orlando to Chicago, returning Sun, Jan 11, priced at $114 just found

Sat, Feb 14 - Sat, Feb 21

MCO

Orlando

MDW

Chicago

$117 Roundtrip, found 7 hours ago

$117

Roundtrip

found 7 hours ago

Select Southwest Airlines flight, departing Sat, Feb 14 from Orlando to Chicago, returning Sat, Feb 21, priced at $117 found 7 hours ago