Cheap flights To Little Gasparilla Island (RSW) from $45

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Cheap Flights to Little Gasparilla Island from $45 One Way, $100 Round Trip

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

Fri, Apr 24 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$100 Roundtrip, found 12 hours ago
$100
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Fri, Apr 24 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $100 found 12 hours ago
Sun, Apr 26 - Sat, May 2
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Apr 26 from O'Hare Intl. to Southwest Florida Intl., returning Sat, May 2, priced at $102 found 2 hours ago
Fri, Apr 24 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$111 Roundtrip, found 12 hours ago
$111
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Fri, Apr 24 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $111 found 12 hours ago
Wed, Aug 26 - Wed, Sep 2
PVD
T.F. Green
RSW
Southwest Florida Intl.
$122 Roundtrip, found 4 hours ago
$122
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from T.F. Green to Southwest Florida Intl., returning Wed, Sep 2, priced at $122 found 4 hours ago
Thu, Aug 20 - Fri, Aug 28
CAK
Akron-Canton
RSW
Southwest Florida Intl.
$138 Roundtrip, just found
$138
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Aug 20 from Akron-Canton to Southwest Florida Intl., returning Fri, Aug 28, priced at $138 just found
Wed, Aug 19 - Sat, Aug 29
BDL
Bradley Intl.
SRQ
Sarasota-Bradenton Intl.
$142 Roundtrip, found 5 hours ago
$142
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from Bradley Intl. to Sarasota-Bradenton Intl., returning Sat, Aug 29, priced at $142 found 5 hours ago
Sat, Dec 5 - Wed, Dec 9
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Dec 9, priced at $142 found 2 days ago
Thu, Aug 20 - Thu, Aug 27
BDL
Bradley Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 14 hours ago
$152
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Thu, Aug 20 from Bradley Intl. to Southwest Florida Intl., returning Thu, Aug 27, priced at $152 found 14 hours ago
Sat, Aug 22 - Sat, Aug 29
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$162 Roundtrip, found 5 hours ago
$162
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Aug 22 from T.F. Green to Sarasota-Bradenton Intl., returning Sat, Aug 29, priced at $162 found 5 hours ago
Tue, Apr 14 - Wed, Apr 29
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Apr 14 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Wed, Apr 29, priced at $177 found 5 days ago

Little Gasparilla Island Flight Information

Traveling To
Little Gasparilla Island
Destination Airport IATA Code
RSW
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Breeze Airways
Flight Price
$100
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 22 - May 25

3 night stay

Minneapolis (MSP) to Fort Myers (RSW)

Delta • Coach

Fort Myers (RSW) to Minneapolis (MSP)

Frontier Airlines • Coach
Price was $891, price is now $643 per person
$643
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

May 21 - May 25

4 night stay

Boston (BOS) to Fort Myers (RSW)

Delta • Non-stop • Coach

Fort Myers (RSW) to Boston (BOS)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,866, price is now $1,273 per person
$1,273
per person
found 1 day ago
Windward Passage Resort
2.0-star property

Windward Passage Resort

May 7 - May 10

3 night stay

Boston (BOS) to Fort Myers (RSW)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,718, price is now $1,241 per person
$1,241
per person
found 1 day ago
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Little Gasparilla Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Sarasota/Lakewood Ranch
3.0-star property

Hampton Inn & Suites Sarasota/Lakewood Ranch

9.4/10 Exceptional! (880 reviews)

May 15 - May 19

4 night stay

Boston (BOS) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Boston (BOS)

United • Non-stop • FirstClass
Price was $1,247, price is now $1,160 per person
$1,160
per person
found 1 day ago
The staff and breakfast

Reviewed on Dec 13, 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)

May 15 - May 19

4 night stay

Boston (BOS) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Boston (BOS)

United • Non-stop • FirstClass
Price was $1,477, price is now $1,375 per person
$1,375
per person
found 1 day ago
Beautiful property and location

Reviewed on Aug 7, 2025

Seaside at Anna Maria Island Inn
3.0-star property

Seaside at Anna Maria Island Inn

9.6/10 Exceptional! (79 reviews)

May 15 - May 19

4 night stay

Boston (BOS) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Boston (BOS)

United • Non-stop • FirstClass
Price was $3,864, price is now $3,612 per person
$3,612
per person
found 1 day ago
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See all available trips from Boston to Little Gasparilla Island
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Little Gasparilla Island

Save more on flights to Little Gasparilla Island while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Little Gasparilla Island

Now it is easier than ever to find a discount Little Gasparilla Island flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Little Gasparilla Island

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Little Gasparilla Island flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Little Gasparilla Island a breeze.

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 $100 and $177 this week. Kicking off your journey from Chicago (ORD)? The lowest one-way tickets started at just $45.
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.