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

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Cheap Flights to Little Gasparilla Island from $44 One Way, $87 Round Trip

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

Mon, Mar 23 - Thu, Mar 26
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Mar 23 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Thu, Mar 26, priced at $87 just found
Wed, Mar 25 - Sat, Mar 28
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$88 Roundtrip, found 20 hours ago
$88
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Wed, Mar 25 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Sat, Mar 28, priced at $88 found 20 hours ago
Sun, Apr 26 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$89 Roundtrip, just found
$89
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Apr 26 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $89 just found
Tue, Apr 14 - Wed, Apr 15
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$122 Roundtrip, found 6 days ago
$122
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Apr 14 from Logan Intl. to Southwest Florida Intl., returning Wed, Apr 15, priced at $122 found 6 days ago
Sat, Dec 5 - Wed, Dec 9
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$134 Roundtrip, found 4 days ago
$134
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Dec 9, priced at $134 found 4 days ago
Sat, Mar 21 - Wed, Mar 25
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$163 Roundtrip, found 5 hours ago
$163
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Sat, Mar 21 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Wed, Mar 25, priced at $163 found 5 hours ago
Sun, May 17 - Thu, May 28
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$187 Roundtrip, just found
$187
Roundtrip
just found
Select Sun Country Airlines flight, departing Sun, May 17 from Minneapolis - St. Paul Intl. to Southwest Florida Intl., returning Thu, May 28, priced at $187 just found
Sun, Oct 18 - Thu, Oct 22
MSP
Minneapolis - St. Paul Intl.
SRQ
Sarasota-Bradenton Intl.
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Sun, Oct 18 from Minneapolis - St. Paul Intl. to Sarasota-Bradenton Intl., returning Thu, Oct 22, priced at $191 found 4 days ago
Wed, May 13 - Sat, May 16
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, May 13 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, May 16, priced at $205 found 5 days ago
Sat, May 2 - Sat, May 16
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$210 Roundtrip, found 4 days ago
$210
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, May 2 from O'Hare Intl. to Southwest Florida Intl., returning Sat, May 16, priced at $210 found 4 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, Sun Country Airlines, JetBlue Airways, American Airlines
Flight Price
$87
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.
The Suites at Fishermen’s Village- 2 Bedroom Suites
3.0-star property

The Suites at Fishermen’s Village- 2 Bedroom Suites

May 2 - May 7

5 night stay

Boston (BOS) to Fort Myers (RSW)

Delta • Coach

Fort Myers (RSW) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,123, price is now $715 per person
$715
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 7 - May 11

4 night stay

Boston (BOS) to Fort Myers (RSW)

American Airlines • Non-stop • Coach

Fort Myers (RSW) to Boston (BOS)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,370, price is now $927 per person
$927
per person
found 1 day ago
Marriott Sanibel Harbour Resort & Spa
4.0-star property

Marriott Sanibel Harbour Resort & Spa

Apr 28 - May 3

5 night stay

Boston (BOS) to Fort Myers (RSW)

Spirit Airlines • Coach

Fort Myers (RSW) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,194, price is now $852 per person
$852
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.
EVEN Hotel Sarasota-Lakewood Ranch by IHG
3.5-star property

EVEN Hotel Sarasota-Lakewood Ranch by IHG

8.4/10 Very Good! (1,002 reviews)

Apr 20 - Apr 25

5 night stay

New York (LGA) to Sarasota (SRQ)

Delta • Roundtrip • PremiumEconomy
Price was $1,344, price is now $1,045 per person
$1,045
per person
found 1 day ago
It was an excellent experience, highly recommed!

Reviewed on Jul 10, 2023

Legacy Hotel at IMG Academy
4.0-star property

Legacy Hotel at IMG Academy

9/10 Wonderful! (960 reviews)

Apr 20 - Apr 25

5 night stay

New York (LGA) to Sarasota (SRQ)

Delta • Roundtrip • PremiumEconomy
Price was $1,385, price is now $1,073 per person
$1,073
per person
found 1 day 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

Compass Hotel by Margaritaville Anna Maria Sound
4.0-star property

Compass Hotel by Margaritaville Anna Maria Sound

9.4/10 Exceptional! (1,986 reviews)

Apr 20 - Apr 25

5 night stay

New York (LGA) to Sarasota (SRQ)

Delta • Roundtrip • PremiumEconomy
Price was $1,379, price is now $1,157 per person
$1,157
per person
found 1 day ago
Beautiful property and location

Reviewed on Aug 7, 2025

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Little Gasparilla Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
Matanzas Inn Bayside Resort and Marina
3.0-star property

Matanzas Inn Bayside Resort and Marina

9.4/10 Exceptional! (1,021 reviews)

May 2 - May 7

5 night stay

New York (NYC) to Fort Myers (RSW)

American Airlines • Roundtrip • FirstClass
Price was $1,536, price is now $1,280 per person
$1,280
per person
found 1 day ago
Excellent customer service and beautiful place with walkable distance to the beach and bars

Reviewed on Sep 14, 2025

Casa Ybel Resort
2.5-star property

Casa Ybel Resort

8.8/10 Excellent! (311 reviews)

May 2 - May 7

5 night stay

New York (NYC) to Fort Myers (RSW)

American Airlines • Roundtrip • FirstClass
Price was $2,278, price is now $1,822 per person
$1,822
per person
found 1 day ago
Great family friendly resort. Beach is amazing. Room was close to beach with screened in porch - had ceiling fan so it was always comfortable sitting outside.

Reviewed on Apr 3, 2021

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Little Gasparilla Island

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You can now book flights to Little Gasparilla Island on the new cutting-edge mobile tool for Android or iPhone users. Hotel packages, flight updates and changes can all be accessed using this tool. When you make any reservations or bookings using this service, confirmation will be provided on the same day the request was made. Take advantage of Orbitz friendly service and low cost Little Gasparilla Island flights.

Discounted tickets available for flights to Little Gasparilla Island

Orbitz offers tickets at a discounted, budget friendly rate that will satisfy all of your travel requirements. Book your Little Gasparilla Island flights with us and structure a package that includes car hire, family activities and cheap accommodation. Orbitz will ensure that all your requirements are met, letting you relax and enjoy your holiday as it was intended.

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Discounted flights to Little Gasparilla Island ensure that all who want to travel can Take advantage of Orbitz’ guaranteed low prices and affordable packages. You will enjoy a hassle free trip, an up to date travel planner and friendly service.

Traveler profile updates

When flying with Orbitz, take advantage of frequent updates on your flights to Little Gasparilla Island. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Little Gasparilla Island flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

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 $87 and $210 this week. Kicking off your journey from Detroit (DTW)? 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.