Cheap flights To Little Gasparilla Island (RSW) from $29

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Cheap Flights to Little Gasparilla Island from $29 One Way, $65 Round Trip

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

Sat, Jan 10 - Sat, Jan 17
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$65 Roundtrip, just found
$65
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jan 10 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Jan 17, priced at $65 just found
Sat, Feb 21 - Sun, Mar 1
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$67 Roundtrip, found 10 hours ago
$67
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Mar 1, priced at $67 found 10 hours ago
Tue, Feb 24 - Sat, Feb 28
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$70 Roundtrip, just found
$70
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Feb 24 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Feb 28, priced at $70 just found
Mon, Feb 23 - Fri, Feb 27
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Feb 23 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Fri, Feb 27, priced at $80 just found
Fri, Jan 30 - Thu, Feb 26
PVD
T.F. Green
RSW
Southwest Florida Intl.
$105 Roundtrip, found 3 hours ago
$105
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Fri, Jan 30 from T.F. Green to Southwest Florida Intl., returning Thu, Feb 26, priced at $105 found 3 hours ago
Mon, Jan 26 - Wed, Feb 4
PVD
T.F. Green
SRQ
Sarasota-Bradenton Intl.
$112 Roundtrip, found 1 hour ago
$112
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Mon, Jan 26 from T.F. Green to Sarasota-Bradenton Intl., returning Wed, Feb 4, priced at $112 found 1 hour ago
Sat, Feb 21 - Sat, Feb 28
PVD
T.F. Green
RSW
Southwest Florida Intl.
$115 Roundtrip, found 2 hours ago
$115
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Feb 21 from T.F. Green to Southwest Florida Intl., returning Sat, Feb 28, priced at $115 found 2 hours ago
Sat, Jan 17 - Sat, Jan 24
EWR
Newark Liberty Intl. Airport
SRQ
Sarasota-Bradenton Intl.
$125 Roundtrip, found 22 hours ago
$125
Roundtrip
found 22 hours ago
Select United flight, departing Sat, Jan 17 from Newark Liberty Intl. Airport to Sarasota-Bradenton Intl., returning Sat, Jan 24, priced at $125 found 22 hours ago
Sat, Jan 17 - Wed, Jan 21
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 20 hours ago
$127
Roundtrip
found 20 hours ago
Select United flight, departing Sat, Jan 17 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Wed, Jan 21, priced at $127 found 20 hours ago
Sun, Jan 25 - Fri, Jan 30
BDL
Bradley Intl.
RSW
Southwest Florida Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Jan 25 from Bradley Intl. to Southwest Florida Intl., returning Fri, Jan 30, priced at $137 found 4 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, JetBlue Airways, Southwest Airlines, Breeze Airways, United
Flight Price
$65
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.
Hilton Garden Inn Ft Myers
3.0-star property

Hilton Garden Inn Ft Myers

Feb 3 - Feb 11

8 night stay

Boston (BOS) to Fort Myers (RSW)

Southwest Airlines • Non-stop • Coach

Fort Myers (RSW) to Boston (BOS)

JetBlue Airways • Non-stop • Coach
Price was $1,255, price is now $551 per person
$551
per person
found 1 day ago
Delray House With Hot tub & Game Room
3.5-star property

Delray House With Hot tub & Game Room

Feb 7 - Feb 14

7 night stay

Boston (BOS) to Sarasota (SRQ)

Southwest Airlines • Non-stop • Coach

Sarasota (SRQ) to Boston (BOS)

JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,343, price is now $603 per person
$603
per person
found 7 hours ago
Innovation Hotel
4.0-star property

Innovation Hotel

Jan 31 - Feb 6

6 night stay

Boston (BOS) to Fort Myers (RSW)

JetBlue Airways • Roundtrip • Coach
Price was $2,156, price is now $1,161 per person
$1,161
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 Tampa Airport Avion Park Westshore
2.5-star property

Hampton Inn & Suites Tampa Airport Avion Park Westshore

9.2/10 Wonderful! (2,566 reviews)

Jan 23 - Jan 25

2 night stay

Chicago (ORD) to Sarasota (SRQ)

United • FirstClass

Sarasota (SRQ) to Chicago (ORD)

Delta • FirstClass
Price was $886, price is now $807 per person
$807
per person
found 20 hours ago
The front desk clerk was very friendly and helpful and provided excellent customer service! The room and the whole hotel very clean. So glad we booked this hotel!

Reviewed on Nov 6, 2025

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
4.0-star property

The Westshore Grand, A Tribute Portfolio Hotel, Tampa

8.6/10 Excellent! (1,751 reviews)

Jan 23 - Jan 25

2 night stay

Chicago (ORD) to Sarasota (SRQ)

United • FirstClass

Sarasota (SRQ) to Chicago (ORD)

Delta • FirstClass
Price was $1,007, price is now $888 per person
$888
per person
found 20 hours ago
Fantastic only the beds feel more like full size beds than queen beds that could be better and better size pillows

Reviewed on Nov 16, 2025

Hampton Inn Tampa Downtown Channel District
3.0-star property

Hampton Inn Tampa Downtown Channel District

9.4/10 Exceptional! (2,021 reviews)

Jan 23 - Jan 25

2 night stay

Chicago (ORD) to Sarasota (SRQ)

United • FirstClass

Sarasota (SRQ) to Chicago (ORD)

Delta • FirstClass
Price was $1,054, price is now $954 per person
$954
per person
found 20 hours ago
This is a very nice hotel with a great location. We were able to walk to some good restaurants and the Channelside area. Breakfast was decent and the pool was very serene when we were there.

Reviewed on Dec 5, 2025

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

Reach your destination without breaking your budget by booking your flights to Little Gasparilla Island using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Little Gasparilla Island Flight

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Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Little Gasparilla Island. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Little Gasparilla Island, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Little Gasparilla Island flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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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 $65 and $137 this week. Kicking off your journey from Chicago (ORD)? The lowest one-way tickets started at just $29.
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.