Cheap Flight Deals to Windermere FL from CA $124

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Windermere?

The cheapest prices found with in the last 7 days for return flights were CA $114 and CA $124 for one-way flights to Windermere for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSOrlandoDecember 4 to December 17CA $114
LGAOrlandoDecember 10 to January 6CA $126
PHLOrlandoJanuary 4 to January 7CA $134
EWROrlandoDecember 14 to December 21CA $135
DTWOrlandoFebruary 5 to February 5CA $155
ORDOrlandoJanuary 8 to January 10CA $163
JFKOrlandoDecember 4 to December 4CA $226
SJUOrlandoFebruary 1 to February 2CA $227
LAXOrlandoDecember 9 to December 17CA $233
MSPOrlandoDecember 14 to December 20CA $234
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
BOSOrlandoNovember 23 to November 27CA $243
DTWOrlandoNovember 24 to November 28CA $306
LGAOrlandoNovember 24 to November 28CA $313
EWROrlandoNovember 24 to November 28CA $321
SJUOrlandoNovember 23 to November 25CA $408
ORDOrlandoNovember 23 to November 30CA $494
JFKOrlandoNovember 24 to November 28CA $551
LAXOrlandoNovember 23 to November 30CA $594
*Prices include taxes and fees

Your guide to flights to Windermere, FL

Flair Airlines fly to Windermere, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Windermere FL currently costs between CA $114 and CA $594. Prices vary, but for the best fares, travel in January when prices are at their lowest.  

Top tips for finding cheap flights to Windermere  

The cheapest flight for a round trip to Windermere is currently CA $114. When you search for flights to Windermere, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Windermere for nearby days.  The cheapest month to travel to Windermere is January from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Windermere 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Windermere with Travelocity 

We have top deals on plane tickets even for last minute flights to Windermere, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Windermere for less. 

Best Windermere Flight and Hotel Packages

Windermere flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
Meliá Orlando Celebration
Reunion Resort & Golf Club
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See all available trips from Halifax to Windermere
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Windermere flight + hotel packages - premium economy flights

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
Westgate Blue Tree Resort in Lake Buena Vista
Westgate Palace Hotel / Universal / I-Drive
Don't see what you're looking for?
See all available trips from Toronto to Windermere
View all trips

Windermere flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
Conrad Orlando
Westgate Cocoa Beach Resort
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See all available trips from Toronto to Windermere
View all trips

Windermere flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
The Delaney Hotel
Summerville Vacation Homes by Columbia Management
Meliá Orlando Celebration
Don't see what you're looking for?
See all available trips from Toronto to Windermere
View all trips

Need a car after flight to Windermere?

Lowest prices found within the past 11 days. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Which airlines fly to Windermere?
20 airlines advertise flights to the city of Windermere, making it one of the world’s largest airline hubs. Most wise wanderers recommend these carriers:

  • Southwest Airlines
  • Spirit Airlines
  • Delta Air Lines

What airport is best to fly into Windermere?
Orlando Intl. Airport is around 24 kilometers from all the hustle and bustle of downtown Windermere. It’s the sole airport servicing the city, so you don’t have to worry about your cab driver taking you to the wrong one!
Where to stay in Windermere
With 1,544 fantastic properties in Windermere, you’re spoilt for choice. But don’t wait around. The sooner you book, the sooner you can start counting down the days until your adventure!Lavish rooms, high thread-count sheets and great service are what you’ll discover when you book the Arnold Palmer’s Bay Hill Club & Lodge or the Disney’s Contemporary Resort. Don’t think you’ll be spending much time in your room? Consider budget options like the OYO Townhouse Orlando West and the Econo Lodge International Drive and splash out on unforgettable experiences instead.
Places to visit in Windermere
Travelers flock to get a glimpse of famous sights in rain, hail or shine. So, whatever the forecast’s like in Windermere, there’s no reason for you to miss out on Walt Disney World®, and Universal Studios Florida.Ignore all those dull tourist traps. Ardent sightseers will want to head straight to wonderful attractions like Magic Kingdom® Park, and Universal’s Islands of Adventure.0 Need some more ideas? 0 But that’s not all there is. 0
How to get through airport security fast when traveling to Windermere
Your trip to Windermere starts as soon as you’ve completed the security checks. Here is a list of useful tips to make sure you pass through quickly:

  • Airport security will expect to see your passport and boarding pass at the checkpoint. Store them in an accessible place, so they’re ready for inspection.
  • Bear in mind that metal belt buckles can set off the body scanner’s alarms. If you’re wearing one, you may be asked to remove it before moving forward.
  • Electronic items such as laptops, phones and cameras need to be sent through the X-ray machine separately. Be sure to have them within easy reach.
  • When you approach the security checkpoint, you’ll be asked to place all gels, liquids and creams in a separate bin for scanning. Make sure they’re all packed in containers smaller than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Undo your shoelaces as you approach the body scanner. Depending on the type of shoes you’ve got on, security may instruct you to remove them.
  • Stash any pocketknives or other sharp and pointy items inside your checked luggage. Security personnel don’t allow such things in carry-on baggage.

Plane Tickets To Windermere

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Windermere. Browse through our inventory to explore a wide range of cheap flights to Windermere to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Windermere as you anxiously await to exit the plane and explore what Windermere has to offer. Considering all the amazing local food and culture in Windermere, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Windermere to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Windermere without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Windermere with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Windermere today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.