Flights from Chicago to Highland Beach

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.

Tue, Jul 29 - Sat, Aug 2

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 Tue, Jul 29 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Aug 2, priced at $138 found 1 day ago

Tue, Jun 24 - Sat, Jun 28

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$143 Roundtrip, found 4 days ago

$143

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jun 24 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Jun 28, priced at $143 found 4 days ago

Mon, Jul 28 - Sat, Aug 2

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$148 Roundtrip, found 1 day ago

$148

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jul 28 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Aug 2, priced at $148 found 1 day ago

Tue, Jun 24 - Fri, Jun 27

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$153 Roundtrip, found 4 days ago

$153

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jun 24 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Jun 27, priced at $153 found 4 days ago

Mon, Jul 28 - Fri, Aug 1

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$158 Roundtrip, found 1 day ago

$158

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Mon, Jul 28 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Aug 1, priced at $158 found 1 day ago

Sat, Jun 28 - Mon, Jun 30

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$163 Roundtrip, found 4 days ago

$163

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 30, priced at $163 found 4 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$163 Roundtrip, found 4 days ago

$163

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Jun 24, priced at $163 found 4 days ago

Tue, Jun 24 - Mon, Jun 30

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$168 Roundtrip, found 4 days ago

$168

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jun 24 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 30, priced at $168 found 4 days ago

Fri, Jun 20 - Mon, Jun 23

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$168 Roundtrip, found 4 days ago

$168

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 23, priced at $168 found 4 days ago

Fri, Jun 27 - Mon, Jun 30

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Fri, Jun 27 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 30, priced at $170 found 4 days ago

Thu, Jun 26 - Mon, Jun 30

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$173 Roundtrip, found 4 days ago

$173

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 30, priced at $173 found 4 days ago

Fri, Jun 20 - Mon, Jun 23

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$177 Roundtrip, found 4 days ago

$177

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Mon, Jun 23, priced at $177 found 4 days ago

Thu, Jun 19 - Fri, Jun 20

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$178 Roundtrip, found 4 days ago

$178

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Thu, Jun 19 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Jun 20, priced at $178 found 4 days ago

Thu, Sep 25 - Thu, Sep 25

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$211 Roundtrip, found 4 days ago

$211

Roundtrip

found 4 days ago

Select Delta flight, departing Thu, Sep 25 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Sep 25, priced at $211 found 4 days ago

Mon, Sep 22 - Thu, Sep 25

MDW

Midway Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$212 Roundtrip, found 4 days ago

$212

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Mon, Sep 22 from Midway Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Sep 25, priced at $212 found 4 days ago

Wed, Nov 12 - Wed, Nov 19

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$215 Roundtrip, found 3 days ago

$215

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Nov 12 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Nov 19, priced at $215 found 3 days ago

Wed, Nov 12 - Thu, Nov 20

ORD

O'Hare Intl.

PBI

Palm Beach Intl.

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select JetBlue Airways flight, departing Wed, Nov 12 from O'Hare Intl. to Palm Beach Intl., returning Thu, Nov 20, priced at $217 found 5 days ago

Thu, Jul 31 - Sun, Aug 3

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$217 Roundtrip, found 1 day ago

$217

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jul 31 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Sun, Aug 3, priced at $217 found 1 day ago

Wed, Nov 12 - Fri, Nov 21

ORD

O'Hare Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$223 Roundtrip, found 3 days ago

$223

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Nov 12 from O'Hare Intl. to Fort Lauderdale - Hollywood Intl., returning Fri, Nov 21, priced at $223 found 3 days ago

Sat, Nov 15 - Sat, Nov 22

MDW

Midway Intl.

PBI

Palm Beach Intl.

$233 Roundtrip, found 5 days ago

$233

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Nov 15 from Midway Intl. to Palm Beach Intl., returning Sat, Nov 22, priced at $233 found 5 days ago