Cheap flights To Windley Key (MIA) from $30

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Cheap Flights to Windley Key from $30 One Way, $58 Round Trip

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

Tue, Jan 13 - Sat, Jan 24
LGA
LaGuardia
MIA
Miami Intl.
$58 Roundtrip, found 9 hours ago
$58
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Tue, Jan 13 from LaGuardia to Miami Intl., returning Sat, Jan 24, priced at $58 found 9 hours ago
Sat, Feb 28 - Wed, Mar 4
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$58 Roundtrip, found 8 hours ago
$58
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Feb 28 from John F. Kennedy Intl. to Miami Intl., returning Wed, Mar 4, priced at $58 found 8 hours ago
Tue, Jan 20 - Tue, Jan 27
BOS
Logan Intl.
MIA
Miami Intl.
$61 Roundtrip, found 6 hours ago
$61
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Jan 20 from Logan Intl. to Miami Intl., returning Tue, Jan 27, priced at $61 found 6 hours ago
Fri, Jan 23 - Thu, Jan 29
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$82 Roundtrip, found 4 hours ago
$82
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Fri, Jan 23 from Newark Liberty Intl. Airport to Miami Intl., returning Thu, Jan 29, priced at $82 found 4 hours ago
Tue, Mar 3 - Tue, Mar 24
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Mar 3 from Newark Liberty Intl. Airport to Miami Intl., returning Tue, Mar 24, priced at $117 found 2 days ago
Fri, Jan 23 - Thu, Jan 29
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$123 Roundtrip, found 4 hours ago
$123
Roundtrip
found 4 hours ago
Select United flight, departing Fri, Jan 23 from Newark Liberty Intl. Airport to Miami Intl., returning Thu, Jan 29, priced at $123 found 4 hours ago
Sun, Feb 1 - Tue, Feb 10
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$123 Roundtrip, found 10 hours ago
$123
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Feb 1 from John F. Kennedy Intl. to Miami Intl., returning Tue, Feb 10, priced at $123 found 10 hours ago
Sat, Jan 10 - Tue, Jan 13
BOS
Logan Intl.
EYW
Key West Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Jan 10 from Logan Intl. to Key West Intl., returning Tue, Jan 13, priced at $147 found 2 days ago
Thu, Jan 29 - Thu, Feb 5
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Jan 29 from Newark Liberty Intl. Airport to Key West Intl., returning Thu, Feb 5, priced at $167 found 6 days ago
Mon, Jan 19 - Mon, Jan 26
LGA
LaGuardia
EYW
Key West Intl.
$175 Roundtrip, found 5 days ago
$175
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Jan 19 from LaGuardia to Key West Intl., returning Mon, Jan 26, priced at $175 found 5 days ago

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, United, Delta, American Airlines, JetBlue Airways, Southwest Airlines
Flight Price
$58
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.
Hawks Cay Resort
4.0-star property

Hawks Cay Resort

Jan 19 - Jan 24

5 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,228, price is now $604 per person
$604
per person
found 1 day ago
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

Feb 5 - Feb 9

4 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Coach

Miami (MIA) to Boston (BOS)

American Airlines • Coach
Price was $1,805, price is now $831 per person
$831
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

Feb 6 - Feb 9

3 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $13,995, price is now $6,833 per person
$6,833
per person
found 1 day ago
Don't see what you're looking for?
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Windley Key premium economy 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! (385 reviews)

Jan 22 - Jan 25

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Roundtrip • PremiumEconomy
Price was $1,205, price is now $823 per person
$823
per person
found 1 day ago
Service was great. Staff was super attentive and helpful. Room was clean. Outlets were tricky as one wasn't working and learned the hardway when my phone lost its charge in the morning. Beach was right across the street. I liked they put a towel and water bottle in the backpack beach chairs.

Reviewed on Dec 10, 2025

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • PremiumEconomy

Key West (EYW) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Save 100% on your flight
Price was $3,510, price is now $2,216 per person
$2,216
per person
found 1 day ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Hyatt Vacation Club at Windward Pointe, Key West
3.5-star property

Hyatt Vacation Club at Windward Pointe, Key West

9.6/10 Exceptional! (1,002 reviews)

Feb 12 - Feb 16

4 night stay

Boston (BOS) to Key West (EYW)

American Airlines • PremiumEconomy

Key West (EYW) to Boston (BOS)

JetBlue Airways • PremiumEconomy
Price was $2,015, price is now $1,395 per person
$1,395
per person
found 1 day ago
Pool and service was great!!! Staff always pleasant and helpful!

Reviewed on Dec 6, 2025

Don't see what you're looking for?
See all available trips from Boston to Windley Key
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Windley Key first 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! (385 reviews)

Jan 29 - Feb 3

5 night stay

Philadelphia (PHL) to Miami (MIA)

American Airlines • Non-stop • FirstClass

Miami (MIA) to Philadelphia (PHL)

Delta • Non-stop • FirstClass
Price was $1,823, price is now $1,242 per person
$1,242
per person
found 1 day ago
Service was great. Staff was super attentive and helpful. Room was clean. Outlets were tricky as one wasn't working and learned the hardway when my phone lost its charge in the morning. Beach was right across the street. I liked they put a towel and water bottle in the backpack beach chairs.

Reviewed on Dec 10, 2025

Seacoast Suites on Miami Beach
3.5-star property

Seacoast Suites on Miami Beach

6.4/10 (1,352 reviews)

Jan 24 - Jan 30

6 night stay

Philadelphia (PHL) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to Philadelphia (PHL)

Delta • FirstClass
Price was $3,486, price is now $2,531 per person
$2,531
per person
found 11 hours ago
Would stay here again!

Reviewed on Jun 21, 2024

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (505 reviews)

Feb 13 - Feb 16

3 night stay

Chicago (ORD) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Price was $3,124, price is now $2,195 per person
$2,195
per person
found 8 hours ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.

Reviewed on Jan 5, 2025

Don't see what you're looking for?
See all available trips from Philadelphia to Windley Key
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Windley Key

Struggling to find international and domestic flights that suit your budget. Consider one of the cheaper options available when you book your flight with Orbitz, where you get guaranteed low prices

Orbitz becomes your Mobile friend

You can now book flights to Windley Key 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 Windley Key flights.

Discounted tickets available for flights to Windley Key

Orbitz offers tickets at a discounted, budget friendly rate that will satisfy all of your travel requirements. Book your Windley Key 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.

Orbitz offers discounted Windley Key flights

Discounted flights to Windley Key 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 Windley Key. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Windley Key flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

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 $58 and $175 this last week. The cheapest one-way ticket prices were $30, 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.