Flights from Chicago to South Florida

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.

Thu, Jul 24 - Sat, Jul 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$110 Roundtrip, found 1 day ago

$110

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jul 24 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jul 26, priced at $110 found 1 day ago

Wed, Jul 16 - Sat, Jul 19

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$120 Roundtrip, found 4 days ago

$120

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jul 19, priced at $120 found 4 days ago

Sun, Jul 20 - Sat, Jul 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$130 Roundtrip, found 1 day ago

$130

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jul 20 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jul 26, priced at $130 found 1 day ago

Wed, Nov 12 - Wed, Nov 12

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$133 Roundtrip, found 22 hours ago

$133

Roundtrip

found 22 hours ago

Select Spirit Airlines flight, departing Wed, Nov 12 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Nov 12, priced at $133 found 22 hours ago

Tue, Jul 22 - Tue, Jul 29

ORD

O'Hare Intl.

MIA

Miami Intl.

$138 Roundtrip, found 2 days ago

$138

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Miami Intl., returning Tue, Jul 29, priced at $138 found 2 days ago

Wed, Jul 16 - Fri, Jul 18

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$140 Roundtrip, found 4 days ago

$140

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Jul 18, priced at $140 found 4 days ago

Thu, Sep 18 - Thu, Sep 25

ORD

O'Hare Intl.

TPA

Tampa Intl.

$150 Roundtrip, found 6 days ago

$150

Roundtrip

found 6 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 6 days ago

Thu, Sep 18 - Thu, Sep 25

ORD

O'Hare Intl.

TPA

Tampa Intl.

$157 Roundtrip, found 6 days ago

$157

Roundtrip

found 6 days ago

Select American Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Tampa Intl., returning Thu, Sep 25, priced at $157 found 6 days ago

Sun, Sep 7 - Fri, Sep 26

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select United flight, departing Sun, Sep 7 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Sep 26, priced at $159 found 1 day ago

Thu, Sep 18 - Thu, Sep 25

ORD

O'Hare Intl.

TPA

Tampa Intl.

$179 Roundtrip, found 6 days ago

$179

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Thu, Sep 18 from O'Hare Intl. to Tampa Intl., returning Thu, Sep 25, priced at $179 found 6 days ago

Sat, Jul 26 - Wed, Jul 30

ORD

O'Hare Intl.

TPA

Tampa Intl.

$197 Roundtrip, found 4 days ago

$197

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Jul 26 from O'Hare Intl. to Tampa Intl., returning Wed, Jul 30, priced at $197 found 4 days ago

Sun, Sep 7 - Fri, Sep 26

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$215 Roundtrip, found 1 day ago

$215

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, Sep 7 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Sep 26, priced at $215 found 1 day ago

Tue, Aug 5 - Wed, Aug 6

MDW

Midway Intl.

MIA

Miami Intl.

$217 Roundtrip, just found

$217

Roundtrip

just found

Select Delta flight, departing Tue, Aug 5 from Midway Intl. to Miami Intl., returning Wed, Aug 6, priced at $217 just found

Wed, Aug 6 - Tue, Aug 12

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$237 Roundtrip, found 6 days ago

$237

Roundtrip

found 6 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 6 days ago

Tue, Aug 19 - Tue, Sep 9

ORD

O'Hare Intl.

EYW

Key West Intl.

$269 Roundtrip, found 3 days ago

$269

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Aug 19 from O'Hare Intl. to Key West Intl., returning Tue, Sep 9, priced at $269 found 3 days ago

Mon, Jul 14 - Mon, Jul 21

MDW

Midway Intl.

RSW

Southwest Florida Intl.

$379 Roundtrip, found 4 days ago

$379

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Jul 14 from Midway Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $379 found 4 days ago

Wed, Jan 28 - Sat, Feb 7

ORD

O'Hare Intl.

SRQ

Sarasota-Bradenton Intl.

$383 Roundtrip, found 3 days ago

$383

Roundtrip

found 3 days ago

Select United flight, departing Wed, Jan 28 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Sat, Feb 7, priced at $383 found 3 days ago

Tue, Dec 2 - Sun, Dec 14

MDW

Midway Intl.

MLB

Orlando Melbourne Intl.

$437 Roundtrip, found 3 days ago

$437

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Dec 2 from Midway Intl. to Orlando Melbourne Intl., returning Sun, Dec 14, priced at $437 found 3 days ago

Tue, Dec 2 - Sat, Dec 13

ORD

O'Hare Intl.

MLB

Orlando Melbourne Intl.

$437 Roundtrip, found 3 days ago

$437

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Dec 2 from O'Hare Intl. to Orlando Melbourne Intl., returning Sat, Dec 13, priced at $437 found 3 days ago

Mon, Jul 14 - Mon, Jul 21

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$11,654 Roundtrip, found 4 days ago

$11,654

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $11,654 found 4 days ago