$44 Cheap flight deals from Detroit (DTT) to Windermere (ORL)

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This Weekend's Flight Deals from Detroit to Windermere

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 11 - Thu, Oct 16
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$205 Roundtrip, found 1 hour ago
$205
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Oct 11 from Detroit Metropolitan Wayne County to Orlando Intl., returning Thu, Oct 16, priced at $205 found 1 hour ago
Sun, Oct 12 - Tue, Oct 28
FNT
Bishop Intl.
MCO
Orlando Intl.
$399 Roundtrip, found 2 days ago
$399
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Oct 12 from Bishop Intl. to Orlando Intl., returning Tue, Oct 28, priced at $399 found 2 days ago

Airfares from $44 One Way, $79 Round Trip from Detroit to Windermere

Prices starting at $79 for return flights and $44 for one-way flights to Windermere were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 11 - Sat, Oct 25
DTW
Detroit
MCO
Orlando
$79 Roundtrip, found 2 days ago
$79
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Oct 11 from Detroit to Orlando, returning Sat, Oct 25, priced at $79 found 2 days ago
Sat, Oct 18 - Sat, Oct 25
DTW
Detroit
MCO
Orlando
$88 Roundtrip, found 7 hours ago
$88
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Sat, Oct 18 from Detroit to Orlando, returning Sat, Oct 25, priced at $88 found 7 hours ago
Mon, Oct 27 - Thu, Oct 30
DTW
Detroit
MCO
Orlando
$88 Roundtrip, found 6 hours ago
$88
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Mon, Oct 27 from Detroit to Orlando, returning Thu, Oct 30, priced at $88 found 6 hours ago
Sat, Oct 25 - Thu, Oct 30
DTW
Detroit
MCO
Orlando
$90 Roundtrip, found 3 hours ago
$90
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Oct 25 from Detroit to Orlando, returning Thu, Oct 30, priced at $90 found 3 hours ago
Tue, Nov 11 - Fri, Nov 14
DTW
Detroit
MCO
Orlando
$172 Roundtrip, found 4 hours ago
$172
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Tue, Nov 11 from Detroit to Orlando, returning Fri, Nov 14, priced at $172 found 4 hours ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (1,001 reviews)

Nov 21 - Nov 24

3 night stay

Detroit (DTT) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $579, price is now $334 per person
$334
per person
found 19 hours ago
Originally got a one bedroom villa and got a free upgrade to a two bedroom which was perfect. The villa was super clean, easy access, washer/dryer, kitchen fully stored with pots, pans, utensils, cups, and plates. They had enough towels for our entire stay, and even had beach towels as well. They had everything that you needed. I didn’t need to call the front desk for anything my entire stay. I loved that place and the size of the villa was perfect for the two of us and maybe more. Definitely will come back if I’m ever back in Orlando.

Reviewed on Jun 11, 2025

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8.2/10 Very Good! (5,346 reviews)

Nov 24 - Nov 30

6 night stay

Detroit (DTT) to Orlando (MCO)

Southwest Airlines • Coach

Orlando (MCO) to Detroit (DTT)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,213, price is now $633 per person
$633
per person
found 1 day ago
It was ok for the price

Reviewed on Sep 27, 2025

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
3.5-star property

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

8.8/10 Excellent! (569 reviews)

Nov 18 - Nov 24

6 night stay

Detroit (DTW) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,197, price is now $755 per person
$755
per person
found 1 day ago
This is the place to stay if you want a real feel for the warmth & charm of St.Augustine & its people instead of a cold impersonal hotel. The staff provided wonderful support in every need of our visit. Their breakfast & coffee are excellent and will accommodate any request if possible. We stayed 1night for the Christmas Nights of Lights and I can safely say that we will be back. The plus side, the beach is a five walk from the hotel. At Checkout, Selim was so gracious and lovely. We will be back in the summer for sure.

Reviewed on Dec 23, 2023

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Windermere first class flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Orlando Airport
4.0-star property

DoubleTree by Hilton Orlando Airport

8.6/10 Excellent! (1,752 reviews)

Nov 11 - Nov 15

4 night stay

Detroit (DTW) to Orlando (MCO)

Delta • Roundtrip • FirstClass
Price was $1,050, price is now $856 per person
$856
per person
found 1 day ago
Our first room smelled like mold and front desk was extremely helpful and switched us right away!

Reviewed on Sep 28, 2025

Hyatt Regency Orlando
4.5-star property

Hyatt Regency Orlando

9.2/10 Wonderful! (1,736 reviews)

Nov 11 - Nov 15

4 night stay

Detroit (DTW) to Orlando (MCO)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $7,003, price is now $5,605 per person
$5,605
per person
found 1 day ago
The valet parking is terrible we waited long to have the car taken away and waited very long for the car to be brought at check out over half hour its just a bit much it can be handled better i think

Reviewed on Jun 29, 2025

The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,003 reviews)

Nov 11 - Nov 15

4 night stay

Detroit (DTW) to Orlando (MCO)

Delta • Roundtrip • FirstClass
Price was $1,529, price is now $1,228 per person
$1,228
per person
found 1 day ago
Great location for hospital access

Reviewed on Jul 8, 2025

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More About Flying To Windermere from Detroit

Route Information for Flights from Detroit to Windermere

Origin Airport IATA Code
DTT
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Detroit to Windermere

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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.