Cheap flights To Windley Key (MIA) from $95

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Windley Key from $95 One Way, $190 Round Trip

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

Wed, Aug 26 - Wed, Sep 2
LGA
LaGuardia
MIA
Miami Intl.
$190 Roundtrip, found 22 hours ago
$190
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from LaGuardia to Miami Intl., returning Wed, Sep 2, priced at $190 found 22 hours ago
Tue, Aug 18 - Wed, Aug 19
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Aug 19, priced at $190 found 4 hours ago
Tue, Aug 18 - Wed, Aug 19
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$194 Roundtrip, found 4 hours ago
$194
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Aug 18 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Aug 19, priced at $194 found 4 hours ago
Tue, Jun 16 - Tue, Jun 23
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$195 Roundtrip, found 1 hour ago
$195
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Jun 16 from Newark Liberty Intl. Airport to Miami Intl., returning Tue, Jun 23, priced at $195 found 1 hour ago
Fri, May 29 - Sat, Jun 6
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Delta flight, departing Fri, May 29 from John F. Kennedy Intl. to Miami Intl., returning Sat, Jun 6, priced at $197 just found
Thu, Jun 4 - Sat, Jun 6
JFK
John F. Kennedy Intl.
MIA
Miami Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select American Airlines flight, departing Thu, Jun 4 from John F. Kennedy Intl. to Miami Intl., returning Sat, Jun 6, priced at $197 just found
Tue, Jun 9 - Wed, Jun 10
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Jun 10, priced at $198 found 2 days ago
Sat, Aug 22 - Sat, Aug 29
LGA
LaGuardia
MIA
Miami Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sat, Aug 22 from LaGuardia to Miami Intl., returning Sat, Aug 29, priced at $217 found 1 hour ago
Wed, May 27 - Wed, Jun 3
EWR
Newark Liberty Intl. Airport
MIA
Miami Intl.
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select United flight, departing Wed, May 27 from Newark Liberty Intl. Airport to Miami Intl., returning Wed, Jun 3, priced at $217 found 1 hour ago
Wed, Aug 5 - Tue, Aug 11
EWR
Newark Liberty Intl. Airport
EYW
Key West Intl.
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 5 from Newark Liberty Intl. Airport to Key West Intl., returning Tue, Aug 11, priced at $309 found 2 days ago

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, American Airlines, Delta, United, Southwest Airlines, JetBlue Airways
Flight Price
$190
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.
Creekside Inn
2.5-star property

Creekside Inn

Jun 17 - Jun 24

7 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $849, price is now $470 per person
$470
per person
found 1 day ago
The W - Bayshore Unit 1003
3.0-star property

The W - Bayshore Unit 1003

Jul 2 - Jul 6

4 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Roundtrip • Coach
Price was $1,802, price is now $751 per person
$751
per person
found 1 day ago
Lime Tree Bay Resort
3.5-star property

Lime Tree Bay Resort

Jun 17 - Jun 24

7 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,653, price is now $916 per person
$916
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Windley Key
View all trips

Windley Key premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Family Pool Home by Hollywood Beach
2.5-star property

Family Pool Home by Hollywood Beach

No reviews

Jun 17 - Jun 21

4 night stay

New York (NYC) to Miami (MIA)

Frontier Airlines • Non-stop • PremiumEconomy

Miami (MIA) to New York (NYC)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $1,621, price is now $1,011 per person
$1,011
per person
found 1 day ago
1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,501 reviews)

Jun 20 - Jun 23

3 night stay

New York (LGA) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,337, price is now $1,560 per person
$1,560
per person
found 14 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,139 reviews)

Jun 20 - Jun 23

3 night stay

New York (LGA) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,550, price is now $1,080 per person
$1,080
per person
found 14 hours ago
The hotel is clean. The staff will greet you but not immediately. The rooms are ok but the beds are small and everything is built for shorter stature people. I am average and the beds and toilet are short! TV's are older. Everything is average and ok.

Reviewed on Jan 19, 2026

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

Windley Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,139 reviews)

Jun 19 - Jun 22

3 night stay

New York (LGA) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to New York (LGA)

Frontier Airlines • FirstClass
Price was $1,713, price is now $1,233 per person
$1,233
per person
found 14 hours ago
The hotel is clean. The staff will greet you but not immediately. The rooms are ok but the beds are small and everything is built for shorter stature people. I am average and the beds and toilet are short! TV's are older. Everything is average and ok.

Reviewed on Jan 19, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,501 reviews)

Jun 19 - Jun 22

3 night stay

New York (LGA) to Miami (MIA)

American Airlines • FirstClass

Miami (MIA) to New York (LGA)

Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,580, price is now $1,778 per person
$1,778
per person
found 14 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

Kompose Boutique Hotel Miami Airport
3.0-star property

Kompose Boutique Hotel Miami Airport

9/10 Wonderful! (3,535 reviews)

Jun 22 - Jun 26

4 night stay

Philadelphia (PHL) to Miami (MIA)

Delta • Non-stop roundtrip • FirstClass
Price was $3,226, price is now $2,298 per person
$2,298
per person
found 1 day ago
Stayed at the Kompose the night before our food. Very nice clean modern hotel. Beds were comfortable, food was great, staff was helpful and kind. Will definitely stay again when in Miami.

Reviewed on May 15, 2026

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

Windley Key

Traveling to Windley Key and need a cheap flight? Orbitz has great deals on flights to Windley Key right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Windley Key Quickly and Hassle-Free

There are many Internet sites that promise cheap Windley Key flights, but a busy, bargain-minded trip planner needs more than just budget air tickets. Not only does Orbitz offer the best deals for domestic and international air fare, but we also provide the resources and tools to help you plan your flights to Windley Key, book your lodging, and look up key attractions in Windley Key. Our easy search tools and guaranteed low prices let you budget your time and your money so you have more of both to spend on your vacation.

New Apps Make Booking Windley Key Flights Easier Than Ever

You no longer need to be sitting at your computer to find amazing Orbitz sales for flights to Windley Key now we offer cutting-edge mobile tools for many Android and iOS gadgets. These free apps allow you to run a search for discount air fare, look for special vacation packages, or check on your booked Windley Key flights from any location. Some special deals are only available for mobile customers, so be sure to take advantage of these free downloads today.

Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Windley Key or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Windley Key flights. When you need us, we’re here for you!

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 $190 and $309 this last week. The cheapest one-way ticket prices were $95, coming from New York (EWR).
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.