$79 Cheap Southwest Airlines flights Orlando (MCO) to Chicago (MDW)

$79 Cheap Southwest Airlines flights Orlando (MCO) to Chicago (MDW)

Prices were available within the past 7 days and start at $79 for one-way flights and $135 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 26 - Sat, Aug 30

MCO

Orlando

MDW

Chicago

$135 Roundtrip, found 13 hours ago

$135

Roundtrip

found 13 hours ago

Select Southwest Airlines flight, departing Tue, Aug 26 from Orlando to Chicago, returning Sat, Aug 30, priced at $135 found 13 hours ago

Thu, Aug 7 - Thu, Aug 14

MCO

Orlando

MDW

Chicago

$136 Roundtrip, found 3 hours ago

$136

Roundtrip

found 3 hours ago

Select Southwest Airlines flight, departing Thu, Aug 7 from Orlando to Chicago, returning Thu, Aug 14, priced at $136 found 3 hours ago

Sun, Aug 3 - Thu, Aug 7

MCO

Orlando

MDW

Chicago

$144 Roundtrip, found 4 days ago

$144

Roundtrip

found 4 days ago

Select Southwest Airlines flight, departing Sun, Aug 3 from Orlando to Chicago, returning Thu, Aug 7, priced at $144 found 4 days ago

Thu, Jul 24 - Sat, Jul 26

MCO

Orlando

MDW

Chicago

$145 Roundtrip, found 5 hours ago

$145

Roundtrip

found 5 hours ago

Select Southwest Airlines flight, departing Thu, Jul 24 from Orlando to Chicago, returning Sat, Jul 26, priced at $145 found 5 hours ago

Wed, Aug 27 - Sat, Aug 30

MCO

Orlando

MDW

Chicago

$157 Roundtrip, found 3 hours ago

$157

Roundtrip

found 3 hours ago

Select Southwest Airlines flight, departing Wed, Aug 27 from Orlando to Chicago, returning Sat, Aug 30, priced at $157 found 3 hours ago

Fri, Aug 22 - Mon, Aug 25

MCO

Orlando

MDW

Chicago

$168 Roundtrip, found 4 hours ago

$168

Roundtrip

found 4 hours ago

Select Southwest Airlines flight, departing Fri, Aug 22 from Orlando to Chicago, returning Mon, Aug 25, priced at $168 found 4 hours ago