Cheap flights To Windley Key (MIA) from $32

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 $32 One Way, $60 Round Trip

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

Mon, May 4 - Fri, May 15
RDU
Raleigh - Durham Intl.
MIA
Miami Intl.
$60 Roundtrip, found 7 hours ago
$60
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, May 4 from Raleigh - Durham Intl. to Miami Intl., returning Fri, May 15, priced at $60 found 7 hours ago
Sun, Aug 23 - Tue, Sep 1
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, found 4 hours ago
$82
Roundtrip
found 4 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 4 hours ago
Tue, Jun 2 - Wed, Jun 3
MCO
Orlando Intl.
MIA
Miami Intl.
$99 Roundtrip, found 23 hours ago
$99
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Tue, Jun 2 from Orlando Intl. to Miami Intl., returning Wed, Jun 3, priced at $99 found 23 hours ago
Sun, Apr 26 - Wed, Apr 29
MCO
Orlando Intl.
EYW
Key West Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Apr 26 from Orlando Intl. to Key West Intl., returning Wed, Apr 29, priced at $99 found 1 day ago
Tue, Apr 28 - Thu, Apr 30
TPA
Tampa Intl.
MIA
Miami Intl.
$128 Roundtrip, found 4 days ago
$128
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Tampa Intl. to Miami Intl., returning Thu, Apr 30, priced at $128 found 4 days ago
Sun, Aug 23 - Thu, Aug 27
RDU
Raleigh - Durham Intl.
EYW
Key West Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 23 from Raleigh - Durham Intl. to Key West Intl., returning Thu, Aug 27, priced at $139 found 1 day ago
Mon, Aug 24 - Thu, Aug 27
ORF
Norfolk Intl.
EYW
Key West Intl.
$143 Roundtrip, found 6 hours ago
$143
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Mon, Aug 24 from Norfolk Intl. to Key West Intl., returning Thu, Aug 27, priced at $143 found 6 hours ago
Tue, May 12 - Fri, May 15
MCO
Orlando Intl.
MIA
Miami Intl.
$150 Roundtrip, found 1 day ago
$150
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 12 from Orlando Intl. to Miami Intl., returning Fri, May 15, priced at $150 found 1 day ago
Mon, Apr 27 - Fri, May 1
ORF
Norfolk Intl.
MIA
Miami Intl.
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Norfolk Intl. to Miami Intl., returning Fri, May 1, priced at $162 found 3 days ago
Tue, Jul 28 - Sat, Aug 1
ORF
Norfolk Intl.
MIA
Miami Intl.
$217 Roundtrip, found 9 hours ago
$217
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jul 28 from Norfolk Intl. to Miami Intl., returning Sat, Aug 1, priced at $217 found 9 hours ago

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways, Southwest Airlines, Spirit Airlines, American Airlines, Delta
Flight Price
$60
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 2 - Jun 5

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Coach

Miami (MIA) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,066, price is now $560 per person
$560
per person
found 1 day ago
Pelican Hotel
4.0-star property

Pelican Hotel

May 19 - May 24

5 night stay

Boston (BOS) to Miami (MIA)

Delta • Coach

Miami (MIA) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,327, price is now $715 per person
$715
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.
Casablanca Miami Beach
3.0-star property

Casablanca Miami Beach

5.8/10 (322 reviews)

May 14 - May 18

4 night stay

New York (NYC) to Miami (MIA)

Frontier Airlines • Non-stop • PremiumEconomy

Miami (MIA) to New York (NYC)

Spirit Airlines • Non-stop • PremiumEconomy
Save 100% on your flight
Price was $1,018, price is now $637 per person
$637
per person
found 1 day ago
Very good for the price, Right on the beach, has a kitchen, Ocean view. Very easy check-in check-out. 1 -1/2 Block from Publix supermarket. 30 minutes from Miami International Airport. Will come again.

Reviewed on Apr 8, 2025

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)

May 14 - May 18

4 night stay

Chicago (ORD) to Miami (MIA)

Spirit Airlines • PremiumEconomy

Miami (MIA) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $15,399, price is now $8,672 per person
$8,672
per person
found 1 day ago
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.6/10 Excellent! (1,000 reviews)

May 22 - May 25

3 night stay

Chicago (ORD) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,421, price is now $949 per person
$949
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

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

Windley Key business class flight packages

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel
4.0-star property

Pelican Hotel

9.2/10 Wonderful! (443 reviews)

May 15 - May 17

2 night stay

New York (LGA) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,157, price is now $910 per person
$910
per person
found 1 day ago
My recent stay at the Pelican Hotel was nothing short of delightful. The location is truly exceptional — perfectly situated to enjoy the very best of the area. From the moment I arrived, the warm and friendly atmosphere made me feel completely at ease. The service was impeccable. Both room service and management were consistently professional and courteous, with special appreciation to Oscar, whose attentiveness and genuine hospitality made a lasting impression. The dining experience was outstanding. Every meal was a pleasure, but the fried octopus deserves special mention — perfectly prepared and absolutely unforgettable. The rooms themselves were a highlight: comfortable, thoughtfully appointed, and each with its own unique design that adds charm and character to the stay. The complimentary cocktails were another memorable touch — expertly made and thoroughly enjoyable. Overall, my time at the Pelican Hotel was a wonderful experience from start to finish. I look forward to returning and will gladly book again without hesitation.

Reviewed on Aug 11, 2025

Hotel Riu Plaza Miami Beach
4.0-star property

Hotel Riu Plaza Miami Beach

8/10 Very Good! (1,141 reviews)

May 15 - May 17

2 night stay

New York (LGA) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,321, price is now $1,008 per person
$1,008
per person
found 1 day 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

EAST Miami Residences
5.0-star property

EAST Miami Residences

9.2/10 Wonderful! (115 reviews)

May 15 - May 17

2 night stay

New York (LGA) to Miami (MIA)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,589, price is now $1,223 per person
$1,223
per person
found 1 day ago
Sorry. Nothing stood out. 1) We had issues with our lights. Turning on and off on their own. 2) Housekeeping never came. We had to call and request even though we had the request call button on. The location of the hotel was phenomenal. Connected to the mall, close to a Publix, and many restaurants.

Reviewed on Nov 29, 2025

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.
Creekside Inn
2.5-star property

Creekside Inn

7.8/10 Good! (1,002 reviews)

May 20 - May 23

3 night stay

New York (NYC) to Miami (MIA)

Delta • FirstClass

Miami (MIA) to New York (NYC)

Frontier Airlines • FirstClass
Price was $1,483, price is now $990 per person
$990
per person
found 1 hour 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

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)

May 28 - Jun 2

5 night stay

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

American Airlines • FirstClass

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

Frontier Airlines • FirstClass
Price was $19,129, price is now $10,536 per person
$10,536
per person
found 9 hours ago
The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (542 reviews)

May 15 - May 22

7 night stay

Boston (BOS) to Key West (EYW)

Delta • Non-stop • FirstClass

Key West (EYW) to Boston (BOS)

American Airlines • Non-stop • FirstClass
Price was $5,979, price is now $3,913 per person
$3,913
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

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

Windley Key

Orbitz is your one stop for guaranteed low prices on Windley Key flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Windley Key and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Windley Key Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Windley Key from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with 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 $60 and $217 this last week. The cheapest one-way ticket prices were $32, 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.