South End Vacation Packages for 2025

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

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South End Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
per person
Jul 21 - Jul 25
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Edison Mall and Barbara B Mann Hall are located nearby.

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 25
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Times Square are located nearby.

GreenLinks Golf Villas at Lely Resort

GreenLinks Golf Villas at Lely Resort

3 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 25
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3-star spa aparthotel in Naples. Enjoy free parking, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Flamingo Island Course - Lely Resort and Swamp Buggy Races are located nearby.

Bellasera Resort

Bellasera Resort

4 out of 5
Old Naples
Save 100% on your flight
per person
Jul 21 - Jul 25
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.

Embassy Suites by Hilton Fort Myers Estero

Embassy Suites by Hilton Fort Myers Estero

3.5 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 25
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby.

The Vistas At Eastwood Apartments By Barsala

The Vistas At Eastwood Apartments By Barsala

4 out of 5
Eastwood Village
Save 100% on your flight
per person
Jul 21 - Jul 25
found 24 hours ago
Roundtrip flight included
Chicago (ORD) to Fort Myers (RSW)
Stay at this 4-star aparthotel in Fort Myers. Enjoy free WiFi, a fitness center, and in-room washers/dryers. Popular attractions Edison Mall and Calusa Nature Center and Planetarium are located nearby.

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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.

Frontier Airlines
Mon, Jul 28 - Thu, Jul 31
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$146 Roundtrip, found 4 days ago
$146
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jul 28 from Hopkins Intl. to Southwest Florida Intl., returning Thu, Jul 31, priced at $146 found 4 days ago
Spirit Airlines
Thu, Jun 26 - Fri, Jul 4
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Jun 26 from O'Hare Intl. to Southwest Florida Intl., returning Fri, Jul 4, priced at $150 found 2 days ago
United
Sun, Jun 22 - Sat, Jul 12
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jun 22 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, Jul 12, priced at $157 found 1 day ago
Delta
Tue, Jul 8 - Tue, Jul 15
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 8 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Tue, Jul 15, priced at $159 found 5 days ago