Cheap flights To Windley Key (MIA) from $29

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 $29 One Way, $56 Round Trip

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

Mon, Jun 1 - Thu, Jun 4
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Jun 1 from Raleigh - Durham Intl. to Miami Intl., returning Thu, Jun 4, priced at $56 found 1 day ago
Sun, Aug 23 - Tue, Sep 1
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, found 6 hours ago
$82
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, Aug 23 from Tampa Intl. to Key West Intl., returning Tue, Sep 1, priced at $82 found 6 hours ago
Mon, Apr 13 - Thu, Apr 16
BOS
Logan Intl.
MIA
Miami Intl.
$103 Roundtrip, just found
$103
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Apr 13 from Logan Intl. to Miami Intl., returning Thu, Apr 16, priced at $103 just found
Wed, Apr 29 - Fri, May 1
MCO
Orlando Intl.
EYW
Key West Intl.
$104 Roundtrip, found 8 hours ago
$104
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Apr 29 from Orlando Intl. to Key West Intl., returning Fri, May 1, priced at $104 found 8 hours ago
Sun, May 3 - Mon, May 4
TPA
Tampa Intl.
MIA
Miami Intl.
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, May 3 from Tampa Intl. to Miami Intl., returning Mon, May 4, priced at $119 found 3 days ago
Wed, Apr 15 - Thu, Apr 16
MCO
Orlando Intl.
MIA
Miami Intl.
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Apr 15 from Orlando Intl. to Miami Intl., returning Thu, Apr 16, priced at $139 found 2 days ago
Tue, May 12 - Thu, May 14
MCO
Orlando Intl.
MIA
Miami Intl.
$143 Roundtrip, found 14 hours ago
$143
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Tue, May 12 from Orlando Intl. to Miami Intl., returning Thu, May 14, priced at $143 found 14 hours ago
Thu, Aug 27 - Thu, Sep 3
RDU
Raleigh - Durham Intl.
EYW
Key West Intl.
$143 Roundtrip, found 3 hours ago
$143
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Raleigh - Durham Intl. to Key West Intl., returning Thu, Sep 3, priced at $143 found 3 hours ago
Wed, Jun 3 - Wed, Jun 10
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jun 3 from Raleigh - Durham Intl. to Miami Intl., returning Wed, Jun 10, priced at $150 found 2 days ago
Sat, Apr 25 - Thu, Apr 30
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$153 Roundtrip, found 13 hours ago
$153
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Apr 25 from Raleigh - Durham Intl. to Miami Intl., returning Thu, Apr 30, priced at $153 found 13 hours ago

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways, Spirit Airlines, Southwest Airlines, American Airlines, Delta, United
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.
Creekside Inn
2.5-star property

Creekside Inn

Apr 30 - May 3

3 night stay

Boston (BOS) to Miami (MIA)

American Airlines • Coach

Miami (MIA) to Boston (BOS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,126, price is now $652 per person
$652
per person
found 1 day ago
President Hotel Villa
3.5-star property

President Hotel Villa

Apr 29 - May 3

4 night stay

Boston (BOS) to Miami (MIA)

Delta • Coach

Miami (MIA) to Boston (BOS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,413, price is now $874 per person
$874
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.
Winslow's Bungalows - Key West Historic Inns
4.0-star property

Winslow's Bungalows - Key West Historic Inns

9.2/10 Wonderful! (1,194 reviews)

May 15 - May 21

6 night stay

New York (NYC) to Key West (EYW)

United • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,382, price is now $1,634 per person
$1,634
per person
found 21 hours ago
The room was clean and location was great

Reviewed on Feb 22, 2026

The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (536 reviews)

May 15 - May 21

6 night stay

New York (NYC) to Key West (EYW)

United • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $5,192, price is now $3,011 per person
$3,011
per person
found 21 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

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

Hyatt Vacation Club at Windward Pointe, Key West

9.4/10 Exceptional! (1,020 reviews)

May 15 - May 21

6 night stay

New York (NYC) to Key West (EYW)

United • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,525, price is now $1,705 per person
$1,705
per person
found 21 hours ago
Staff was fantastic, room and grounds very clean and well kept.

Reviewed on Feb 12, 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.
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,007 reviews)

May 20 - May 24

4 night stay

New York (NYC) to Miami (MIA)

Delta • Non-stop • FirstClass

Miami (MIA) to New York (NYC)

Spirit Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $1,472, price is now $934 per person
$934
per person
found 14 hours ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

Creekside Inn
2.5-star property

Creekside Inn

7.8/10 Good! (1,027 reviews)

May 4 - May 7

3 night stay

Chicago (ORD) to Miami (MIA)

Delta • Non-stop • FirstClass

Miami (MIA) to Chicago (ORD)

United • Non-stop • FirstClass
Price was $1,578, price is now $1,062 per person
$1,062
per person
found 21 hours ago
Leaving a review to let Travellers know that this place deserves a better rating and reviews than what some Travellers have left. We had a great stay! The property is older and could use some upgrades but it was exactly suited for our stay. Property is right on a canal where you can see Tarpon, Manatees and other fish, if you have a boat you can dock right there. Our stay was quiet and peaceful and housekeeping took care of any needs we had. Its within walking distance of a few restaurants, dive shop, bait shop, snorkel tour. I would recommend Lido73, Mar Bar and Old Tavernier restaurants all within walking distance. Just know it not the 4 seasons just and older property that will suit your needs. I would definitely come stay again.

Reviewed on Mar 22, 2026

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

Windley Key

Save money on your flights to Windley Key as well as on hotel and car packages.

 

Free Fees

Snap up cheap Windley Key flights at Orbitz, and pay no booking fees. We also don’t charge fees when your plans change or are cancelled. While you’re there, check out our low fare deals on flights to other locations besides flights to Windley Key.

Everyday Is a Great Day to Save Even More

Get bonus points from Orbitz, the best discount travel planner in the business. Use your Orbitz Visa to take advantage of sales on Windley Key flights, or pile on points by using it for gas, groceries, and other everyday goods and services. Pack your wallet with even more savings using our cutting-edge suite of mobile tools.

Mix and Match

At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Windley Key flights air ticket. Save more on air travel every day in every way at Orbitz.

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 $153 this last week. The cheapest one-way ticket prices were $29, coming from Raleigh (RDU).
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.