South End 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.

Tue, Mar 24 - Wed, Mar 25

DTW

Detroit Metropolitan Wayne County

RSW

Southwest Florida Intl.

$98 Roundtrip, found 1 hour ago

$98

Roundtrip

found 1 hour ago

Select Frontier Airlines flight, departing Tue, Mar 24 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Wed, Mar 25, priced at $98 found 1 hour ago

Tue, Apr 7 - Fri, Apr 24

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$126 Roundtrip, found 6 hours ago

$126

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Tue, Apr 7 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Apr 24, priced at $126 found 6 hours ago

Sat, May 2 - Sat, May 9

EWR

Newark Liberty Intl. Airport

RSW

Southwest Florida Intl.

$197 Roundtrip, found 1 day ago

$197

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, May 2 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, May 9, priced at $197 found 1 day ago

Fri, Apr 10 - Wed, Apr 22

EWR

Newark Liberty Intl. Airport

RSW

Southwest Florida Intl.

$217 Roundtrip, found 4 hours ago

$217

Roundtrip

found 4 hours ago

Select American Airlines flight, departing Fri, Apr 10 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Wed, Apr 22, priced at $217 found 4 hours ago

Sat, May 9 - Sat, May 16

ORD

O'Hare Intl.

RSW

Southwest Florida Intl.

$217 Roundtrip, found 3 hours ago

$217

Roundtrip

found 3 hours ago

Select Southwest Airlines flight, departing Sat, May 9 from O'Hare Intl. to Southwest Florida Intl., returning Sat, May 16, priced at $217 found 3 hours ago