Cheap flights To Little Gasparilla Island (RSW) from $44

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Cheap Flights to Little Gasparilla Island from $44 One Way, $88 Round Trip

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

Sun, Jun 21 - Thu, Jun 25
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$88 Roundtrip, found 1 hour ago
$88
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Jun 21 from Hopkins Intl. to Southwest Florida Intl., returning Thu, Jun 25, priced at $88 found 1 hour ago
Sun, May 10 - Thu, May 14
CLE
Hopkins Intl.
SRQ
Sarasota-Bradenton Intl.
$89 Roundtrip, found 16 hours ago
$89
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, May 10 from Hopkins Intl. to Sarasota-Bradenton Intl., returning Thu, May 14, priced at $89 found 16 hours ago
Sun, Apr 19 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Apr 19 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $93 found 1 day ago
Sun, Apr 19 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 19 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $96 found 1 day ago
Mon, Apr 27 - Thu, Apr 30
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Apr 27 from Logan Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $179 just found
Sat, Dec 5 - Sat, Dec 12
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Dec 5 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Dec 12, priced at $183 just found
Sun, Oct 25 - Thu, Oct 29
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$187 Roundtrip, found 23 hours ago
$187
Roundtrip
found 23 hours ago
Select Sun Country Airlines flight, departing Sun, Oct 25 from Minneapolis - St. Paul Intl. to Sarasota-Bradenton Intl., returning Thu, Oct 29, priced at $187 found 23 hours ago
Wed, May 6 - Tue, May 12
JFK
John F. Kennedy Intl.
RSW
Southwest Florida Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, May 6 from John F. Kennedy Intl. to Southwest Florida Intl., returning Tue, May 12, priced at $189 found 2 days ago
Wed, Apr 22 - Wed, Apr 29
JFK
John F. Kennedy Intl.
SRQ
Sarasota-Bradenton Intl.
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 22 from John F. Kennedy Intl. to Sarasota-Bradenton Intl., returning Wed, Apr 29, priced at $191 found 2 days ago
Tue, May 12 - Fri, May 15
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select United flight, departing Tue, May 12 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Fri, May 15, priced at $192 found 2 days ago

Little Gasparilla Island Flight Information

Traveling To
Little Gasparilla Island
Destination Airport IATA Code
RSW
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Breeze Airways, Delta, Sun Country Airlines, United
Flight Price
$88
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.
Captiva Beach Resort
3.0-star property

Captiva Beach Resort

Jun 2 - Jun 5

3 night stay

Boston (BOS) to Sarasota (SRQ)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $677, price is now $464 per person
$464
per person
found 1 day ago
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton
4.0-star property

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

May 23 - May 27

4 night stay

Boston (BOS) to Fort Myers (RSW)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $780, price is now $503 per person
$503
per person
found 1 day ago
Hilton Marco Island Beach Resort and Spa
4.0-star property

Hilton Marco Island Beach Resort and Spa

May 22 - May 25

3 night stay

Boston (BOS) to Fort Myers (RSW)

Delta • Coach

Fort Myers (RSW) to Boston (BOS)

Southwest Airlines • Coach
Price was $1,406, price is now $982 per person
$982
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.
Legacy Hotel at IMG Academy
4.0-star property

Legacy Hotel at IMG Academy

9/10 Wonderful! (975 reviews)

May 15 - May 20

5 night stay

Boston (BOS) to Sarasota (SRQ)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,098, price is now $822 per person
$822
per person
found 21 hours ago
This is our second time we stayed at Legacy and it has turned into one of my wife’s favorites. My only little “oops” is that it would be nice if the clerk that checked us in made it a point to remind us concerning the 25% off a meal at the restaurant, we didn’t see it until we checked out. We also enjoy dining at the restaurant.

Reviewed on Aug 14, 2025

Marriott Sanibel Harbour Resort & Spa
4.0-star property

Marriott Sanibel Harbour Resort & Spa

8.4/10 Very Good! (1,010 reviews)

May 14 - May 18

4 night stay

Boston (BOS) to Fort Myers (RSW)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,211, price is now $965 per person
$965
per person
found 24 hours ago
The property was very nice. Still rebuilding after the hurricane, main pool was under construction, secondary pool was open. Skeleton staff as it is not peek season. Make sure to bring bug spray, there are little mosquitos that are around all day in Sanibel and Captiva Island. They are actually insane, not eager to return to this area of FL.

Reviewed on Aug 7, 2024

JW Marriott Marco Island Beach Resort
4.0-star property

JW Marriott Marco Island Beach Resort

9/10 Wonderful! (1,002 reviews)

May 14 - May 18

4 night stay

Boston (BOS) to Fort Myers (RSW)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $2,789, price is now $2,417 per person
$2,417
per person
found 24 hours ago
The rooms was clean the staff very friendly,the hotel have a large choose of amenities.

Reviewed on Nov 18, 2025

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

If you are looking for discount prices on flights to Little Gasparilla Island then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Little Gasparilla Island flights easy and affordable.

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With Orbitz’s Display Matrix, booking flights to Little Gasparilla Island is simple. Just one glance gives you all the pricing information you need, including your discounts and savings. View all your options before selecting and booking your perfect Little Gasparilla Island flights.

Manage Travel Plans on the Move

By using Orbitz’s free apps for iPhone and Android, and an easy-to-use mobile browser at m.orbitz.com, booking flights to Little Gasparilla Island has never been so convenient. Check for updates and alerts wherever you are, or manage your booking quickly. And we also offer mobile exclusive deals on hotels, so don’t delay—book right away.

The Complete Package

Orbitz makes it stress-free to book Little Gasparilla Island flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Little Gasparilla Island, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

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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 $88 and $192 this week. Kicking off your journey from Chicago (ORD)? The lowest one-way tickets started at just $44.
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.