Cheap Flights To Windermere 2025

Windermere Flights as Low as $82

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, May 6 - Wed, May 14
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 5 days ago
$82
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 6 from John F. Kennedy Intl. to Orlando Intl., returning Wed, May 14, priced at $82 found 5 days ago
Frontier Airlines
Sat, May 10 - Sat, May 17
ORD
O'Hare Intl.
MCO
Orlando Intl.
$89 Roundtrip, found 5 days ago
$89
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 10 from O'Hare Intl. to Orlando Intl., returning Sat, May 17, priced at $89 found 5 days ago
Frontier Airlines
Tue, May 6 - Thu, May 15
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 6 from John F. Kennedy Intl. to Orlando Intl., returning Thu, May 15, priced at $90 found 5 days ago
Spirit Airlines
Tue, May 20 - Wed, May 21
BOS
Logan Intl.
MCO
Orlando Intl.
$90 Roundtrip, found 22 hours ago
$90
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Tue, May 20 from Logan Intl. to Orlando Intl., returning Wed, May 21, priced at $90 found 22 hours ago
Spirit Airlines
Tue, Jun 3 - Wed, Jun 4
LGA
LaGuardia
MCO
Orlando Intl.
$90 Roundtrip, found 14 hours ago
$90
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Tue, Jun 3 from LaGuardia to Orlando Intl., returning Wed, Jun 4, priced at $90 found 14 hours ago
Frontier Airlines
Sat, May 17 - Thu, May 22
ORD
O'Hare Intl.
MCO
Orlando Intl.
$94 Roundtrip, found 6 days ago
$94
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 17 from O'Hare Intl. to Orlando Intl., returning Thu, May 22, priced at $94 found 6 days ago
Frontier Airlines
Sun, May 11 - Wed, May 14
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$95 Roundtrip, found 5 days ago
$95
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, May 11 from John F. Kennedy Intl. to Orlando Intl., returning Wed, May 14, priced at $95 found 5 days ago
Frontier Airlines
Tue, May 6 - Mon, May 19
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$96 Roundtrip, found 5 days ago
$96
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 6 from John F. Kennedy Intl. to Orlando Intl., returning Mon, May 19, priced at $96 found 5 days ago
Frontier Airlines
Mon, Jun 2 - Sat, Jun 7
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$98 Roundtrip, found 14 hours ago
$98
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Mon, Jun 2 from John F. Kennedy Intl. to Orlando Intl., returning Sat, Jun 7, priced at $98 found 14 hours ago
Delta
Tue, Jun 24 - Sat, Jun 28
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 24 from John F. Kennedy Intl. to Orlando Intl., returning Sat, Jun 28, priced at $167 found 6 days ago
JetBlue Airways
Thu, Jun 5 - Mon, Jun 9
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$167 Roundtrip, found 17 hours ago
$167
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Thu, Jun 5 from John F. Kennedy Intl. to Orlando Intl., returning Mon, Jun 9, priced at $167 found 17 hours ago
American Airlines
Wed, Jun 4 - Tue, Jun 10
LGA
LaGuardia
MCO
Orlando Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jun 4 from LaGuardia to Orlando Intl., returning Tue, Jun 10, priced at $167 found 6 days ago
Frontier Airlines
Tue, Jun 17 - Thu, Jul 3
DEN
Denver Intl.
MCO
Orlando Intl.
$176 Roundtrip, found 19 hours ago
$176
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Tue, Jun 17 from Denver Intl. to Orlando Intl., returning Thu, Jul 3, priced at $176 found 19 hours ago
United
Tue, Sep 2 - Sun, Sep 7
ORD
O'Hare Intl.
MCO
Orlando Intl.
$213 Roundtrip, found 19 hours ago
$213
Roundtrip
found 19 hours ago
Select United flight, departing Tue, Sep 2 from O'Hare Intl. to Orlando Intl., returning Sun, Sep 7, priced at $213 found 19 hours ago
Breeze Airways
Wed, Jul 30 - Sat, Aug 16
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jul 30 from Portsmouth Intl. to Orlando Intl., returning Sat, Aug 16, priced at $237 found 2 days ago
Hawaiian Airlines
Thu, Sep 25 - Wed, Oct 1
DEN
Denver Intl.
MCO
Orlando Intl.
$432 Roundtrip, found 6 days ago
$432
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Thu, Sep 25 from Denver Intl. to Orlando Intl., returning Wed, Oct 1, priced at $432 found 6 days ago

Flight Travel Guide to Windermere

Book your next flight to (airport) if Windermere is calling your name. And with the AARP Travel Center Powered by Expedia®, can become a reality sooner than you think. AARP Travel features members-only discounts with the best rates from Expedia, so members get the best price in travel, guaranteed. As an AARP member, you'll pay no booking fees on flights, and often receive exclusive rates on hotels and car rentals.

Whether this trip is for business or pleasure, we will help you get there (without breaking the bank).

Windermere Airport Transportation

Once you've got your flight scheduled to Windermere with AARP Travel, you might want to book a rental car so you can get around Windermere. You can request Windermere rental cars under our cars tab and get into the driver's seat right when you step out of the airport. For more information, check out the Windermere Car Rentals Guide.

Things to Do in Windermere

Not sure where to start? Not to worry—there's lots to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in Windermere, make sure you look at our "Things to Do in Windermere" page for excursions and activities for the whole family.

Book Your Hotel in Windermere

Windermere has lodging to choose from, so you will have little difficulty finding a place to stay close to all the things you want to see. If you need to stay close to the airport, or another attraction in Windermere, check out our hotel listings page. No matter where you stay, just remember that you will get the best for your trip when you book with us.

Planning Your Trip to Windermere

Whether you are heading out on an exploration to a place you have never been for pleasure, bringing the family on the annual trip, or a business trip, we have the perfect getaway waiting for you. There is no better time than now to start booking that next trip. Book one of our flights today.