Cheap flights To Little Gasparilla Island (RSW) from $51

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Cheap Flights to Little Gasparilla Island from $51 One Way, $118 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Sep 15 - Thu, Sep 24
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Hopkins Intl. to Southwest Florida Intl., returning Thu, Sep 24, priced at $118 found 5 days ago
Sun, Aug 16 - Thu, Aug 20
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$120 Roundtrip, found 13 hours ago
$120
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sun, Aug 16 from Hopkins Intl. to Southwest Florida Intl., returning Thu, Aug 20, priced at $120 found 13 hours ago
Fri, Sep 11 - Sun, Sep 13
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$123 Roundtrip, found 5 days ago
$123
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Sep 11 from Hopkins Intl. to Southwest Florida Intl., returning Sun, Sep 13, priced at $123 found 5 days ago
Wed, Jan 20 - Wed, Jan 27
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jan 20 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Jan 27, priced at $153 found 6 days ago
Tue, Sep 8 - Sat, Sep 12
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 8 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, Sep 12, priced at $177 found 1 day ago
Tue, Sep 22 - Tue, Sep 29
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$177 Roundtrip, found 21 hours ago
$177
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Sep 22 from Logan Intl. to Southwest Florida Intl., returning Tue, Sep 29, priced at $177 found 21 hours ago
Tue, Sep 1 - Tue, Sep 15
JFK
John F. Kennedy Intl.
RSW
Southwest Florida Intl.
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Sep 1 from John F. Kennedy Intl. to Southwest Florida Intl., returning Tue, Sep 15, priced at $181 found 3 days ago
Sun, Jan 10 - Thu, Jan 14
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$187 Roundtrip, found 9 hours ago
$187
Roundtrip
found 9 hours ago
Select Sun Country Airlines flight, departing Sun, Jan 10 from Minneapolis - St. Paul Intl. to Sarasota-Bradenton Intl., returning Thu, Jan 14, priced at $187 found 9 hours ago
Sat, Sep 5 - Sat, Sep 12
JFK
John F. Kennedy Intl.
RSW
Southwest Florida Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Sep 5 from John F. Kennedy Intl. to Southwest Florida Intl., returning Sat, Sep 12, priced at $197 found 5 days ago
Fri, Aug 14 - Mon, Aug 24
BOS
Logan Intl.
SRQ
Sarasota-Bradenton Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Fri, Aug 14 from Logan Intl. to Sarasota-Bradenton Intl., returning Mon, Aug 24, priced at $197 found 5 hours ago

Little Gasparilla Island Flight Information

Traveling To
Little Gasparilla Island
Destination Airport IATA Code
RSW
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways, Southwest Airlines, Sun Country Airlines, United, JetBlue Airways, Delta, American Airlines
Flight Price
$118
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Little Gasparilla Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Fort Myers Cape Coral
2.0-star property

Quality Inn Fort Myers Cape Coral

Aug 8 - Aug 15

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $493, price is now $306 per person
$306
per person
found 1 day ago
Casa Ybel Resort
2.5-star property

Casa Ybel Resort

Aug 8 - Aug 15

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,693, price is now $1,118 per person
$1,118
per person
found 1 day ago
LaPlaya Beach & Golf Resort - A Noble House Resort
4.5-star property

LaPlaya Beach & Golf Resort - A Noble House Resort

Aug 6 - Aug 10

4 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,321, price is now $875 per person
$875
per person
found 1 day ago
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Little Gasparilla Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Inn on Fifth
4.0-star property

Inn on Fifth

9.4/10 Exceptional! (1,001 reviews)

Aug 20 - Aug 27

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,716, price is now $1,088 per person
$1,088
per person
found 1 day ago
Great location! Overall, room was clean and there was no carpet (which is a plus for us). Pool is small but very enjoyable!

Reviewed on Jul 6, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort
4.5-star property

LaPlaya Beach & Golf Resort - A Noble House Resort

9/10 Wonderful! (1,009 reviews)

Aug 20 - Aug 27

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,161, price is now $1,281 per person
$1,281
per person
found 1 day ago
Our son is in a wheelchair. Staff and facility were very accommodating to people with disabilities. All of resort was assessable to us. The rooms were great, pools and beaches were outstanding.

Reviewed on Jul 6, 2026

Casa Ybel Resort
2.5-star property

Casa Ybel Resort

8.8/10 Excellent! (372 reviews)

Aug 20 - Aug 27

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,787, price is now $1,124 per person
$1,124
per person
found 1 day ago
Everything was great

Reviewed on Jul 5, 2026

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Little Gasparilla Island business class flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott - Naples
3.0-star property

Courtyard by Marriott - Naples

8.6/10 Excellent! (682 reviews)

Aug 20 - Aug 27

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • BusinessClass
Price was $1,062, price is now $1,045 per person
$1,045
per person
found 1 day ago
Great and beautiful

Reviewed on Jul 6, 2026

Shangri-La Springs
2.5-star property

Shangri-La Springs

9.2/10 Wonderful! (223 reviews)

Aug 20 - Aug 27

7 night stay

Cleveland (CLE) to Fort Myers (RSW)

Frontier Airlines • Roundtrip • BusinessClass
Price was $1,160, price is now $1,058 per person
$1,058
per person
found 1 day ago
Everything was fine except, with the very hot weather, I was dissappointed the pool was not open. Otherwise, we really enjpyed pout stay. It's an oasis in the middle of hubbub.

Reviewed on Jul 6, 2026

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See all available trips from Cleveland to Little Gasparilla Island
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Little Gasparilla Island

Finding cheap flights to Little Gasparilla Island is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Little Gasparilla Island flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Little Gasparilla Island through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Little Gasparilla Island—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Little Gasparilla Island flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Little Gasparilla Island with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

Which airlines fly to Little Gasparilla Island?
With 20 airlines ready to help you get away to Little Gasparilla Island, finding the ideal flight will be easy. Lock in your airfare with one of these popular carriers that offer services to Southwest Florida Intl. Airport (RSW):

  • Air Canada - 12 flights to Little Gasparilla Island per month
  • EW Discover - 3 flights to Little Gasparilla Island per month
  • WestJet - 3 flights to Little Gasparilla Island per month

How much is a flight to Little Gasparilla Island?
Travelers from far and wide landed round-trip flight bargains ranging between $118 and $197 this week. Kicking off your journey from Cleveland (CLE)? The lowest one-way tickets started at just $51.
How to book the cheapest flight to Little Gasparilla Island?
Picking up cheap flights to Little Gasparilla Island is as easy as booking with Orbitz. But if you'd love to make sure you're nabbing the best flight deals around, here are some suggestions to keep in mind:

  • Taking off from or arriving at other airports can be more affordable. Enter your preferred departure and arrival airports. Next, select the 'Nearby airports' function below to look through your options.
  • If you're flexible with your schedule, click on the 'Show flexible dates' option. It'll bring up flight deals for the days either side of your chosen departure. Fares often vary depending on what day it is.
  • Hit 'Show options' to filter your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • Book as soon as you know your travel dates. While it does happen now and then, airfares rarely get more affordable as your date of departure gets closer.
  • Bundle your hotels, flights and car rentals into a package deal and enjoy discounts. Save your hard-earned dollars for things that really excite you, like discovering every corner of Little Gasparilla Island.
  • Don't fly during peak seasons if you can. By steering clear of summer and school vacations, you can save plenty on your airfares.

What is the best time to book a flight to Little Gasparilla Island?
Generally speaking, January is the best month to purchase your plane ticket. This is followed by February and August. Bear this in mind while you browse for a cheap flight to Little Gasparilla Island.
What day of the week is the cheapest to book a flight to Little Gasparilla Island?
To land an incredible flight deal, book on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days to book flights to Little Gasparilla Island.
What is the cheapest day of the week to fly to Little Gasparilla Island?
You can grab cheap flights to Little Gasparilla Island by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is the next most affordable day, while Saturday has the most expensive ticket prices. Whether you prefer to stretch your travel budget or start your trip on whichever day is convenient, you'll always find a great deal with Orbitz.
What is the cheapest month to fly to Little Gasparilla Island?
To pick up cheap flights to Little Gasparilla Island, you should fly out in August. If saving money on your plane ticket is your main concern, Orbitz data has found that this is generally the best month to jet off. June is when fares are at their highest.
Which airlines allow free cancellation?
Flexibility is important, that's why Orbitz lets you search for airlines that won't hit you with a fee for amendments to your reservation. Fill out your departure and arrival points, then select "Filter by flexible change policies." We'll show you all the options that include free cancellation and no change fees.
What do I need for the flight to Little Gasparilla Island?
There is so much to sort out for any big trip, so it's great to get a little bit of help along the way. Here's a handy checklist to ensure that you're prepared for take off:

  • Make sure you've packed your travel documents and some identification. For international trips, you'll need your passport. When you book your seats, always use the same details that are indicated on your government-issued ID.
  • A properly packed carry-on bag is the key to a great flight experience. Given your flight to Little Gasparilla Island is no short hop, take some snacks and activities to keep you occupied. Something to read or listen to will help pass the time.
  • Air conditioning and high altitudes can create a cool environment. No matter what the weather is in Little Gasparilla Island, bring an extra layer along to keep warm while on the plane.

How do I get cheap first-class/business deals to Little Gasparilla Island?
Smart travelers have a way of finding first or business-class flights to Little Gasparilla Island without the hefty price tag. Be like them with these handy tips:

  • Flexibility doesn't just help with your yoga. Avoid locking in your travel dates so you can snap up cheaper airfares when a huge sale drops.
  • Find a low-cost carrier that has seats in business class. They usually come with extra space and a glass of Champagne — but without the premium price.
  • Take advantage of your airline's loyalty scheme and upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.