Flights from Chicago to Gulf Coast

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Oct 17 - Mon, Oct 20

ORD

O'Hare Intl.

IAH

George Bush Intercontinental

$102 Roundtrip, found 2 days ago

$102

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to George Bush Intercontinental, returning Mon, Oct 20, priced at $102 found 2 days ago

Wed, Jul 16 - Wed, Jul 16

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$105 Roundtrip, found 3 days ago

$105

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Wed, Jul 16, priced at $105 found 3 days ago

Thu, Jul 10 - Sun, Jul 13

ORD

O'Hare Intl.

MCO

Orlando Intl.

$120 Roundtrip, found 1 day ago

$120

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Orlando Intl., returning Sun, Jul 13, priced at $120 found 1 day ago

Thu, Jul 17 - Sun, Jul 27

ORD

O'Hare Intl.

IAH

George Bush Intercontinental

$132 Roundtrip, found 20 hours ago

$132

Roundtrip

found 20 hours ago

Select Frontier Airlines flight, departing Thu, Jul 17 from O'Hare Intl. to George Bush Intercontinental, returning Sun, Jul 27, priced at $132 found 20 hours ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$138 Roundtrip, found 1 day ago

$138

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Aug 23, priced at $138 found 1 day ago

Tue, Jul 22 - Tue, Jul 29

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, found 23 hours ago

$138

Roundtrip

found 23 hours ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Miami Intl., returning Tue, Jul 29, priced at $138 found 23 hours ago

Thu, Sep 18 - Thu, Sep 25

ORD

O'Hare Intl.

TPA

Tampa Intl.

$150 Roundtrip, found 4 days ago

$150

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Tampa Intl., returning Thu, Sep 25, priced at $150 found 4 days ago

Sat, Sep 20 - Sat, Sep 27

ORD

O'Hare Intl.

MCO

Orlando Intl.

$157 Roundtrip, found 3 days ago

$157

Roundtrip

found 3 days ago

Select United flight, departing Sat, Sep 20 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 27, priced at $157 found 3 days ago

Sat, Sep 20 - Sat, Sep 27

ORD

O'Hare Intl.

MCO

Orlando Intl.

$157 Roundtrip, found 3 days ago

$157

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Sep 20 from O'Hare Intl. to Orlando Intl., returning Sat, Sep 27, priced at $157 found 3 days ago

Mon, Aug 4 - Mon, Aug 11

ORD

O'Hare Intl.

MSY

Louis Armstrong New Orleans Intl.

$178 Roundtrip, found 3 days ago

$178

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Mon, Aug 4 from O'Hare Intl. to Louis Armstrong New Orleans Intl., returning Mon, Aug 11, priced at $178 found 3 days ago

Wed, Jul 16 - Wed, Jul 16

ORD

O'Hare Intl.

DAL

Love Field

$191 Roundtrip, found 3 days ago

$191

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Jul 16 from O'Hare Intl. to Love Field, returning Wed, Jul 16, priced at $191 found 3 days ago

Sat, Aug 2 - Sat, Aug 2

ORD

O'Hare Intl.

DFW

Dallas-Fort Worth Intl.

$191 Roundtrip, found 1 day ago

$191

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Aug 2 from O'Hare Intl. to Dallas-Fort Worth Intl., returning Sat, Aug 2, priced at $191 found 1 day ago

Tue, Oct 14 - Tue, Oct 21

MDW

Midway Intl.

MCO

Orlando Intl.

$197 Roundtrip, found 2 days ago

$197

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Oct 14 from Midway Intl. to Orlando Intl., returning Tue, Oct 21, priced at $197 found 2 days ago

Tue, Aug 12 - Wed, Aug 13

MDW

Midway Intl.

MIA

Miami Intl.

$217 Roundtrip, found 2 days ago

$217

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Aug 12 from Midway Intl. to Miami Intl., returning Wed, Aug 13, priced at $217 found 2 days ago

Fri, Dec 5 - Thu, Dec 11

ORD

O'Hare Intl.

MCO

Orlando Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Dec 5 from O'Hare Intl. to Orlando Intl., returning Thu, Dec 11, priced at $217 found 1 day ago

Wed, Aug 6 - Tue, Aug 12

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$237 Roundtrip, found 4 days ago

$237

Roundtrip

found 4 days ago

Select Delta flight, departing Wed, Aug 6 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Aug 12, priced at $237 found 4 days ago

Tue, Jul 22 - Wed, Jul 23

ORD

O'Hare Intl.

SAT

San Antonio Intl.

$238 Roundtrip, found 6 days ago

$238

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Antonio Intl., returning Wed, Jul 23, priced at $238 found 6 days ago

Thu, Jun 19 - Sun, Jun 29

MDW

Midway Intl.

TPA

Tampa Intl.

$267 Roundtrip, found 6 days ago

$267

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, Jun 19 from Midway Intl. to Tampa Intl., returning Sun, Jun 29, priced at $267 found 6 days ago

Tue, Dec 23 - Sun, Dec 28

ORD

O'Hare Intl.

JAX

Jacksonville Intl.

$412 Roundtrip, found 2 days ago

$412

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Dec 23 from O'Hare Intl. to Jacksonville Intl., returning Sun, Dec 28, priced at $412 found 2 days ago

Sun, Jun 15 - Mon, Jun 23

MDW

Midway Intl.

JAX

Jacksonville Intl.

$739 Roundtrip, found 4 days ago

$739

Roundtrip

found 4 days ago

Select Delta flight, departing Sun, Jun 15 from Midway Intl. to Jacksonville Intl., returning Mon, Jun 23, priced at $739 found 4 days ago