Cheap flights To Windley Key (MIA) from $41

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Cheap Flights to Windley Key from $41 One Way, $82 Round Trip

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

Sun, May 3 - Wed, May 6
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, May 3 from Tampa Intl. to Key West Intl., returning Wed, May 6, priced at $82 found 6 hours ago
Wed, May 6 - Tue, May 12
TPA
Tampa Intl.
EYW
Key West Intl.
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, May 6 from Tampa Intl. to Key West Intl., returning Tue, May 12, priced at $82 found 9 hours ago
Sun, May 31 - Thu, Jun 4
MCO
Orlando Intl.
EYW
Key West Intl.
$102 Roundtrip, found 6 hours ago
$102
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, May 31 from Orlando Intl. to Key West Intl., returning Thu, Jun 4, priced at $102 found 6 hours ago
Thu, Apr 23 - Fri, May 1
TPA
Tampa Intl.
MIA
Miami Intl.
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Apr 23 from Tampa Intl. to Miami Intl., returning Fri, May 1, priced at $118 found 6 days ago
Tue, Jun 2 - Wed, Jun 3
MCO
Orlando Intl.
MIA
Miami Intl.
$119 Roundtrip, found 3 days ago
$119
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Jun 2 from Orlando Intl. to Miami Intl., returning Wed, Jun 3, priced at $119 found 3 days ago
Tue, Apr 28 - Wed, May 6
BOS
Logan Intl.
MIA
Miami Intl.
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 28 from Logan Intl. to Miami Intl., returning Wed, May 6, priced at $128 found 1 day ago
Mon, May 25 - Sat, May 30
MCO
Orlando Intl.
MIA
Miami Intl.
$129 Roundtrip, found 4 hours ago
$129
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Mon, May 25 from Orlando Intl. to Miami Intl., returning Sat, May 30, priced at $129 found 4 hours ago
Sat, May 9 - Sat, May 16
TPA
Tampa Intl.
MIA
Miami Intl.
$140 Roundtrip, found 14 hours ago
$140
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Tampa Intl. to Miami Intl., returning Sat, May 16, priced at $140 found 14 hours ago
Mon, Apr 13 - Tue, Apr 21
BOS
Logan Intl.
MIA
Miami Intl.
$165 Roundtrip, found 3 days ago
$165
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Logan Intl. to Miami Intl., returning Tue, Apr 21, priced at $165 found 3 days ago
Sat, May 2 - Fri, May 8
BOS
Logan Intl.
MIA
Miami Intl.
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, May 2 from Logan Intl. to Miami Intl., returning Fri, May 8, priced at $197 found 1 hour ago

Windley Key Flight Information

Traveling To
Windley Key
Destination Airport IATA Code
MIA
Number of Airlines Serving
Airlines
Breeze Airways, Spirit Airlines, Southwest Airlines, American Airlines, Frontier Airlines, Delta
Flight Price
$82
Earliest Departing Flight
Latest Departing Flight

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Windley Key economy flight packages

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

Pelican Hotel

May 24 - May 29

5 night stay

Boston (BOS) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $997, price is now $503 per person
$503
per person
found 1 day ago
Creekside Inn
2.5-star property

Creekside Inn

May 26 - May 29

3 night stay

Boston (BOS) to Miami (MIA)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,046, price is now $540 per person
$540
per person
found 16 hours ago
The Retreat Collection at 1 Hotel & Homes South Beach
5.0-star property

The Retreat Collection at 1 Hotel & Homes South Beach

May 21 - May 24

3 night stay

Boston (BOS) to Miami (MIA)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $12,745, price is now $7,034 per person
$7,034
per person
found 1 day ago
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Windley Key premium economy 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 14 - May 19

5 night stay

Chicago (ORD) to Miami (MIA)

United • Roundtrip • PremiumEconomy
Price was $1,609, price is now $1,024 per person
$1,024
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

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 19

5 night stay

Chicago (ORD) to Miami (MIA)

United • Roundtrip • PremiumEconomy
Price was $19,385, price is now $10,438 per person
$10,438
per person
found 1 day ago
The Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (542 reviews)

Jun 2 - Jun 9

7 night stay

New York (NYC) to Key West (EYW)

United • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,505, price is now $2,210 per person
$2,210
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

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Windley Key business 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! (1,000 reviews)

May 16 - May 19

3 night stay

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

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,264, price is now $882 per person
$882
per person
found 12 hours ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 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 16 - May 19

3 night stay

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

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $11,493, price is now $6,258 per person
$6,258
per person
found 12 hours ago
1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,471 reviews)

May 16 - May 19

3 night stay

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

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,467, price is now $1,786 per person
$1,786
per person
found 12 hours ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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Windley Key first class 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

Chicago (ORD) to Miami (MIA)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,143, price is now $1,401 per person
$1,401
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 Key West Hotel
2.5-star property

The Key West Hotel

9.2/10 Wonderful! (542 reviews)

May 15 - May 20

5 night stay

Boston (BOS) to Key West (EYW)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,901, price is now $2,979 per person
$2,979
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

1 Hotel South Beach
5.0-star property

1 Hotel South Beach

9.4/10 Exceptional! (1,471 reviews)

May 27 - May 31

4 night stay

Boston (BOS) to Miami (MIA)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,407, price is now $2,394 per person
$2,394
per person
found 1 day ago
The best hotel I have ever stayed in!

Reviewed on Jan 17, 2026

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Windley Key

Finding cheap flights to Windley Key is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Windley Key flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Windley Key through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Windley Key—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Windley Key flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Windley Key with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $82 and $197 this last week. The cheapest one-way ticket prices were $41, coming from Tampa (TPA).
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.