Cheap flights To Windley Key (MIA) from $65

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Cheap Flights to Windley Key from $65 One Way, $130 Round Trip

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

Mon, Mar 1 - Tue, Mar 2
LGA
LaGuardia
MIA
Miami Intl.
$130 Roundtrip, found 18 hours ago
$130
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Mar 1 from LaGuardia to Miami Intl., returning Tue, Mar 2, priced at $130 found 18 hours ago
Wed, Nov 4 - Mon, Nov 9
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Nov 4 from Newark Liberty Intl. Airport to Miami Intl., returning Mon, Nov 9, priced at $157 found 1 hour ago
Tue, Nov 10 - Wed, Nov 18
LGA
LaGuardia
MIA
Miami Intl.
$159 Roundtrip, found 9 hours ago
$159
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Nov 10 from LaGuardia to Miami Intl., returning Wed, Nov 18, priced at $159 found 9 hours ago
Wed, Mar 3 - Wed, Mar 10
LGA
LaGuardia
MIA
Miami Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 3 from LaGuardia to Miami Intl., returning Wed, Mar 10, priced at $163 found 1 day ago
Sat, Feb 27 - Mon, Mar 1
LGA
LaGuardia
MIA
Miami Intl.
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Feb 27 from LaGuardia to Miami Intl., returning Mon, Mar 1, priced at $174 found 5 days ago
Wed, Feb 17 - Thu, Feb 18
LGA
LaGuardia
MIA
Miami Intl.
$236 Roundtrip, found 19 hours ago
$236
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Wed, Feb 17 from LaGuardia to Miami Intl., returning Thu, Feb 18, priced at $236 found 19 hours ago
Tue, Nov 10 - Wed, Nov 18
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$239 Roundtrip, just found
$239
Roundtrip
just found
Select American Airlines flight, departing Tue, Nov 10 from John F. Kennedy Intl. to Miami Intl., returning Wed, Nov 18, priced at $239 just found
Wed, Oct 28 - Wed, Nov 4
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$239 Roundtrip, just found
$239
Roundtrip
just found
Select American Airlines flight, departing Wed, Oct 28 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Nov 4, priced at $239 just found
Wed, Oct 28 - Wed, Nov 4
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$239 Roundtrip, just found
$239
Roundtrip
just found
Select United flight, departing Wed, Oct 28 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Nov 4, priced at $239 just found
Tue, Nov 10 - Wed, Nov 18
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$239 Roundtrip, just found
$239
Roundtrip
just found
Select Delta flight, departing Tue, Nov 10 from John F. Kennedy Intl. to Miami Intl., returning Wed, Nov 18, priced at $239 just found

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, JetBlue Airways, American Airlines, United, Delta
Flight Price
$130
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Windley Key economy flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

Nov 12 - Nov 15

3 night stay

Boston (BOS) to Miami (MIA)

Allegiant Air • Coach

Miami (MIA) to Boston (BOS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $965, price is now $587 per person
$587
per person
found 1 day ago
The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

Nov 9 - Nov 12

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Coach

Miami (MIA) to Boston (BOS)

Allegiant Air • Coach
Price was $9,943, price is now $4,987 per person
$4,987
per person
found 1 day ago
Private Oasis at Arya
3.5-star property

Private Oasis at Arya

Nov 12 - Nov 16

4 night stay

Boston (BOS) to Miami (MIA)

Allegiant Air • Coach

Miami (MIA) to Boston (BOS)

American Airlines • Coach
Save 100% on your flight
Price was $1,569, price is now $955 per person
$955
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Windley Key
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Windley Key premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Atlantic Hotel & Spa
4.5-star property

The Atlantic Hotel & Spa

9/10 Wonderful! (1,968 reviews)

Nov 20 - Nov 24

4 night stay

New York (NYC) to Miami (MIA)

JetBlue Airways • PremiumEconomy

Miami (MIA) to New York (NYC)

Allegiant Air • PremiumEconomy
Price was $1,153, price is now $884 per person
$884
per person
found 1 hour ago
amazing

Reviewed on Oct 4, 2026

Pelican Grand Beach Resort - A Noble House Resort
4.0-star property

Pelican Grand Beach Resort - A Noble House Resort

8.8/10 Excellent! (1,741 reviews)

Nov 20 - Nov 24

4 night stay

New York (NYC) to Miami (MIA)

JetBlue Airways • PremiumEconomy

Miami (MIA) to New York (NYC)

Allegiant Air • PremiumEconomy
Save 100% on your flight
Price was $1,413, price is now $931 per person
$931
per person
found 1 hour ago

JW Marriott Turnberry Resort & Spa
4.5-star property

JW Marriott Turnberry Resort & Spa

8.8/10 Excellent! (1,569 reviews)

Nov 20 - Nov 24

4 night stay

New York (NYC) to Miami (MIA)

JetBlue Airways • PremiumEconomy

Miami (MIA) to New York (NYC)

Allegiant Air • PremiumEconomy
Price was $1,345, price is now $1,051 per person
$1,051
per person
found 1 hour ago

Don't see what you're looking for?
See all available trips from New York to Windley Key
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Windley Key business class flight packages

Price found within the past 48 hours. Click for updated prices.
Park Central South Beach
4.0-star property

Park Central South Beach

8.6/10 Excellent! (1,952 reviews)

Nov 20 - Nov 25

5 night stay

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,823, price is now $1,360 per person
$1,360
per person
found 19 hours ago
I hated staying at this hotel and don't understand all the nice reviews on it, my room was all the way at end, coming up from the elevator a guest was at it with a housekeeper about her missing item, now I'm already nervous, so i get to my room the outlet by our bed isn't working and I have a cpap machine can't plug it, phone isn't working went downstairs because i can't call this man come over checked it took a pic i guess to showed his boss he never fixed it anything, the next day housekeeping come she mopped the floor, didn't maks our bed no shower gel so partner had to go downstairs to get soap, we have no washcloth asked housekeeper they speak no English can't understand even with Google translator, now parking it's $48 dollars a day yet you have to wait 20 minutes to get the car for, we ate downstairs 3 little tiny tacos $28 and a salad $22 I couldn't wait to get out, this hotel could be for free ill sleep in the street, so happy I only stayed 2 nights, finally Sunday morning we sleeping 10 am housekeeper knocked on the door then walked right in like it's not even 11 am, when I asked her what time is checked out she couldn't respond, I was so happy when I left this place, but glad it was 11 minutes from the event we went too

Reviewed on Oct 5, 2026

Fontainebleau Miami Beach
4.5-star property

Fontainebleau Miami Beach

8.4/10 Very Good! (9,051 reviews)

Nov 20 - Nov 25

5 night stay

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,929, price is now $1,423 per person
$1,423
per person
found 19 hours ago

Kimpton EPIC Hotel by IHG
5.0-star property

Kimpton EPIC Hotel by IHG

9/10 Wonderful! (2,636 reviews)

Nov 20 - Nov 25

5 night stay

Newark Liberty Intl. Airport (EWR) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,906, price is now $1,425 per person
$1,425
per person
found 19 hours ago
Todo bien

Reviewed on Oct 5, 2026

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Windley Key
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Windley Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,008 reviews)

Nov 9 - Nov 15

6 night stay

Chicago (ORD) to Miami (MIA)

United • Roundtrip • FirstClass
Price was $2,088, price is now $1,372 per person
$1,372
per person
found 1 day ago

The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

8/10 Very Good! (1 review)

Nov 4 - Nov 9

5 night stay

New York (NYC) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $19,877, price is now $10,154 per person
$10,154
per person
found 1 day ago
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8.2/10 Very Good! (1,193 reviews)

Nov 9 - Nov 15

6 night stay

Chicago (ORD) to Miami (MIA)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,670, price is now $1,745 per person
$1,745
per person
found 1 day ago
Todo increíble

Reviewed on Oct 4, 2026

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Windley Key

Save more on flights to Windley Key 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 Windley Key

Now it is easier than ever to find a discount Windley Key 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 Windley Key

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 Windley Key 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 Windley Key a breeze.

Frequently asked questions

Which airlines fly to Windley Key?
With 20 airlines traveling to Key West Intl. Airport (EYW), you'll be making your way around Windley Key in no time at all. Choosing a flight that suits your travel itinerary is easy. Take a look at the fares from these leading air carriers and get ready to touch down at Key West Intl. Airport (EYW):

  • American Airlines - 118 flights to Windley Key per month
  • Silver Airways - 57 flights to Windley Key per month
  • Delta - 45 flights to Windley Key per month

How much is a flight to Windley Key?
If you're hunting down a round-trip, fares ranged between $130 and $244 this last week. The cheapest one-way ticket prices were $65, coming from New York (LGA).
How to book the cheapest flight to Windley Key?
Scoring cheap flights to Windley Key is as easy as booking with Orbitz. But if you want to make sure you're grabbing the best flight deals around, here are some suggestions to follow:

  • Taking off from or landing at nearby airports can save you money. Type in your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below to compare your options.
  • If your travel plans aren't written in stone, click on the 'Show flexible dates' link to check out the flight deals for multiple departure dates. You may find a cheaper fare.
  • To refine your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose your preferred flight times under 'Sort & Filter' to the left.
  • The early bird gets the biggest savings, so purchase your seats once you've settled on your travel dates. The most affordable airfares go like hotcakes and prices increase as the departure date nears.
  • Combine your hotels, flights and car rentals into one convenient package deal. Save your dollars for things you're really excited about, like exploring every corner of Windley Key.
  • Flying during peak season can mean pricey airfares. If possible, plan your vacation outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Windley Key?
Book in January, February or August for the best airfares to Windley Key. Once you've found a bargain, lock it in — cheap flights will appear and then vanish in the click of a mouse.
What day of the week is the cheapest to book a flight to Windley Key?
When it comes to cheap fares to Windley Key, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A fabulous flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Windley Key?
Everybody enjoys saving money, so we recommend departing earlier in the week for cheap flights to Windley Key. Orbitz data from 2020 suggests you can secure the best prices on flights taking off on Mondays. Tuesday is the next cheapest day, while Saturdays are likely to cost a bundle. Many people like to travel at the end of the week, so leave those Saturdays for binge-watching your favorite TV shows.
What is the cheapest month to fly to Windley Key?
To book cheap flights to Windley Key, you should pack your bags and travel in August. Orbitz data has found that generally, this is the best month to save on your airfare. If you're thinking of jetting to Windley Key during June, it's worth keeping in mind that this is the least affordable time of year to take a trip.
Which airlines allow free cancellation?
If you're concerned your travel plans could change, Orbitz will help you find a flexible fare. All you need to do is choose "Filter by flexible change policies" when searching for your Windley Key flights. We'll show you all the airlines that include free cancellation within 24 hours and no change fees — along with awesome low prices.
What do I need for the flight to Windley Key?
Whether you're a regular flyer or it's your first time in the air, it helps to be organized on your trip. Here are several things to bear in mind:

  • For starters, you'll need to take all applicable travel documents and your identification. How much will depend on your place of departure. At the time of booking, always use the correct name, birth date and gender as indicated on your current ID.
  • A well-packed carry-on bag is a must for any lengthy flight. With several hours up your sleeve, you'll probably long for something to keep you entertained while in transit. We suggest a good book (or trashy magazine), and something to nibble on.
  • Both air conditioning and high altitudes can create a cool environment (and we don't mean trendy!). No matter what the season is, bring a sweater along to keep nice and warm while on the plane.

How do I get cheap first-class/business deals to Windley Key?
Smart travelers know how to find first or business-class fares to Windley Key without the sky-high price tag. Take their lead with these helpful tips:

  • Flexibility is important. By being open to different travel dates, you'll have better odds of spotting a sale on first or business-class airfares.
  • Look for a low-cost carrier that has business-class seats. They usually come with more legroom and a glass of Champagne — but without the premium price.
  • Bid for an upgrade in online auctions or upgrade your fare with your frequent flyer points.

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.