Cheap flights To Windley Key (MIA) from $40

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 $40 One Way, $56 Round Trip

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

Wed, Aug 5 - Wed, Aug 12
BWI
Baltimore Washington Intl. Thurgood Marshall
MIA
Miami Intl.
$56 Roundtrip, found 6 days ago
$56
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Baltimore Washington Intl. Thurgood Marshall to Miami Intl., returning Wed, Aug 12, priced at $56 found 6 days ago
Sun, Sep 27 - Thu, Oct 1
PHL
Philadelphia Intl.
MIA
Miami Intl.
$76 Roundtrip, found 21 hours ago
$76
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sun, Sep 27 from Philadelphia Intl. to Miami Intl., returning Thu, Oct 1, priced at $76 found 21 hours ago
Sat, Sep 19 - Thu, Sep 24
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Sep 19 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Thu, Sep 24, priced at $80 just found
Thu, Sep 24 - Mon, Sep 28
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$159 Roundtrip, found 2 hours ago
$159
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Sep 24 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Mon, Sep 28, priced at $159 found 2 hours ago
Thu, Sep 24 - Mon, Sep 28
ATL
Hartsfield-Jackson Atlanta Intl.
MIA
Miami Intl.
$167 Roundtrip, found 2 hours ago
$167
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Sep 24 from Hartsfield-Jackson Atlanta Intl. to Miami Intl., returning Mon, Sep 28, priced at $167 found 2 hours ago
Tue, Oct 6 - Thu, Oct 15
SFO
San Francisco Intl.
MIA
Miami Intl.
$240 Roundtrip, just found
$240
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Oct 6 from San Francisco Intl. to Miami Intl., returning Thu, Oct 15, priced at $240 just found
Sat, Oct 3 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
EYW
Key West Intl.
$279 Roundtrip, found 4 days ago
$279
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Oct 3 from Hartsfield-Jackson Atlanta Intl. to Key West Intl., returning Mon, Oct 5, priced at $279 found 4 days ago
Fri, Sep 18 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
AVT
Aventura Brightline Train Station
$293 Roundtrip, just found
$293
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Sep 18 from Hartsfield-Jackson Atlanta Intl. to Aventura Brightline Train Station, returning Sat, Sep 26, priced at $293 just found
Fri, Sep 18 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
EKW
Miami Central Brightline Train Station
$293 Roundtrip, just found
$293
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Sep 18 from Hartsfield-Jackson Atlanta Intl. to Miami Central Brightline Train Station, returning Sat, Sep 26, priced at $293 just found
Tue, Oct 20 - Fri, Oct 30
BWI
Baltimore Washington Intl. Thurgood Marshall
EYW
Key West Intl.
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Baltimore Washington Intl. Thurgood Marshall to Key West Intl., returning Fri, Oct 30, priced at $319 found 1 day ago

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, American Airlines, Delta, JetBlue Airways
Flight Price
$56
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.
Lyfe Resort & Residences
4.5-star property

Lyfe Resort & Residences

Aug 22 - Aug 24

2 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
Price was $937, price is now $601 per person
$601
per person
found 1 day ago
Casablanca Miami Beach
3.0-star property

Casablanca Miami Beach

Aug 19 - Aug 22

3 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,389, price is now $740 per person
$740
per person
found 1 day ago
Villas At Hawks Cay Resort
4.0-star property

Villas At Hawks Cay Resort

Aug 27 - Aug 30

3 night stay

Detroit (DTW) to Miami (MIA)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,484, price is now $951 per person
$951
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Windley Key
View all trips

Windley Key premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Kimpton EPIC Hotel by IHG
5.0-star property

Kimpton EPIC Hotel by IHG

9/10 Wonderful! (2,517 reviews)

Sep 3 - Sep 7

4 night stay

Detroit (DTW) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,144, price is now $844 per person
$844
per person
found 1 day ago
3 day stay, great location, safe to walk around, and not far from any major site in Miami.

Reviewed on Jul 18, 2026

EAST Miami
5.0-star property

EAST Miami

9.2/10 Wonderful! (3,910 reviews)

Sep 3 - Sep 7

4 night stay

Detroit (DTW) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,438, price is now $1,088 per person
$1,088
per person
found 1 day ago
Wear pants

Reviewed on Jul 18, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,577 reviews)

Aug 20 - Aug 23

3 night stay

Philadelphia (PHL) to Miami (MIA)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,706, price is now $1,220 per person
$1,220
per person
found 1 day ago
Great pool.

Reviewed on Jul 16, 2026

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

Windley Key business class 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! (1,900 reviews)

Aug 24 - Aug 27

3 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Roundtrip • BusinessClass
Price was $769, price is now $621 per person
$621
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)

Aug 24 - Aug 27

3 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $9,053, price is now $4,724 per person
$4,724
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

Lyfe Resort & Residences
4.5-star property

Lyfe Resort & Residences

7/10 Good! (1,787 reviews)

Aug 24 - Aug 27

3 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Roundtrip • BusinessClass
Price was $1,199, price is now $896 per person
$896
per person
found 1 day ago
Christina the outdoor waitress was wonderful she make all our staying dates amazing

Reviewed on Jul 6, 2026

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

Windley Key first class flight packages

Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Miami Beach
5.0-star property

Nobu Hotel Miami Beach

8.6/10 Excellent! (1,433 reviews)

Aug 20 - Aug 24

4 night stay

New York (NYC) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,554, price is now $1,189 per person
$1,189
per person
found 17 hours ago
Stayed for short layover but the hotel was perfect. Wife enjoyed the pool.

Reviewed on Jul 16, 2026

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,577 reviews)

Aug 20 - Aug 24

4 night stay

New York (NYC) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $2,502, price is now $1,838 per person
$1,838
per person
found 17 hours ago
Great pool.

Reviewed on Jul 16, 2026

Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,151 reviews)

Aug 20 - Aug 24

4 night stay

New York (NYC) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Price was $1,722, price is now $1,335 per person
$1,335
per person
found 17 hours ago

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

Windley Key

Snag some “suite” deals when you add cheap hotel rooms to Windley Key flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

Find mobile-only bargains on your home away from home with Orbitz cutting-edge mobile tools. Search domestic and international hotels at Orbitz On the Go. Find free travel planning apps for your iPhone, Android or iPad. You’ll always get our guaranteed low prices on your favorite hotels and flights to Windley Key.

Fun for All

While shopping Orbitz sales on Windley Key flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Windley Key flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Windley Key. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $56 and $319 this last week. The cheapest one-way ticket prices were $40, coming from Philadelphia (PHL).
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.