Gulf Highlands Vacation Packages for 2026

Top Flight Deals

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.

Mon, Aug 24 - Tue, Sep 8

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$214 Roundtrip, found 1 day ago

$214

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Aug 24 from O'Hare Intl. to Pensacola Intl., returning Tue, Sep 8, priced at $214 found 1 day ago

Tue, Jun 16 - Sat, Jul 4

ATL

Hartsfield-Jackson Atlanta Intl.

PNS

Pensacola Intl.

$259 Roundtrip, found 1 hour ago

$259

Roundtrip

found 1 hour ago

Select Delta flight, departing Tue, Jun 16 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Sat, Jul 4, priced at $259 found 1 hour ago

Wed, Jul 8 - Thu, Jul 16

ORD

O'Hare Intl.

PNS

Pensacola Intl.

$261 Roundtrip, found 4 days ago

$261

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jul 8 from O'Hare Intl. to Pensacola Intl., returning Thu, Jul 16, priced at $261 found 4 days ago

Tue, Jun 16 - Sat, Jul 4

ATL

Hartsfield-Jackson Atlanta Intl.

PNS

Pensacola Intl.

$265 Roundtrip, found 1 hour ago

$265

Roundtrip

found 1 hour ago

Select Southwest Airlines flight, departing Tue, Jun 16 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Sat, Jul 4, priced at $265 found 1 hour ago

Tue, Jun 16 - Tue, Jun 30

DFW

Dallas-Fort Worth Intl.

PNS

Pensacola Intl.

$265 Roundtrip, found 3 days ago

$265

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Jun 16 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Tue, Jun 30, priced at $265 found 3 days ago