South End Vacation Packages for 2025

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.

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$80 Roundtrip, found 3 days ago

$80

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $80 found 3 days ago

Tue, Sep 9 - Tue, Sep 23

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$127 Roundtrip, found 4 days ago

$127

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Sep 9 from Logan Intl. to Southwest Florida Intl., returning Tue, Sep 23, priced at $127 found 4 days ago

Sat, Sep 13 - Tue, Sep 23

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$127 Roundtrip, found 4 days ago

$127

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Sep 13 from Logan Intl. to Southwest Florida Intl., returning Tue, Sep 23, priced at $127 found 4 days ago

Fri, Sep 19 - Fri, Sep 26

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$132 Roundtrip, found 3 days ago

$132

Roundtrip

found 3 days ago

Select United flight, departing Fri, Sep 19 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Sep 26, priced at $132 found 3 days ago

Tue, Sep 16 - Sat, Sep 20

CLE

Hopkins Intl.

RSW

Southwest Florida Intl.

$169 Roundtrip, found 1 day ago

$169

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Tue, Sep 16 from Hopkins Intl. to Southwest Florida Intl., returning Sat, Sep 20, priced at $169 found 1 day ago