$71 Cheap flight deals from Madison (MSN) to The Villages (MCO)

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This Weekend's Flight Deals from Madison to The Villages

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.

Sun, Nov 23 - Mon, Nov 24
MSN
Dane County Regional
MCO
Orlando Intl.
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Nov 23 from Dane County Regional to Orlando Intl., returning Mon, Nov 24, priced at $267 found 6 days ago

Airfares from $71 One Way, $156 Round Trip from Madison to The Villages

Prices starting at $156 for return flights and $71 for one-way flights to The Villages were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Nov 24 - Wed, Nov 26
MSN
Madison
MCO
Orlando
$156 Roundtrip, found 6 days ago
$156
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Nov 24 from Madison to Orlando, returning Wed, Nov 26, priced at $156 found 6 days ago
Wed, Nov 19 - Wed, Dec 3
MSN
Madison
MCO
Orlando
$165 Roundtrip, found 6 hours ago
$165
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Nov 19 from Madison to Orlando, returning Wed, Dec 3, priced at $165 found 6 hours ago
Wed, Jan 28 - Wed, Feb 4
MSN
Madison
MCO
Orlando
$173 Roundtrip, found 2 hours ago
$173
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Jan 28 from Madison to Orlando, returning Wed, Feb 4, priced at $173 found 2 hours ago
Mon, Jan 5 - Wed, Jan 14
MSN
Madison
MCO
Orlando
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jan 5 from Madison to Orlando, returning Wed, Jan 14, priced at $179 found 4 days ago
Wed, Jan 21 - Wed, Feb 4
MSN
Madison
MCO
Orlando
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jan 21 from Madison to Orlando, returning Wed, Feb 4, priced at $183 found 3 days ago

The Villages economy flight packages

Price found within the past 48 hours. Click for updated prices.
Vero Beach Inn & Suites I-95
3.0-star property

Vero Beach Inn & Suites I-95

8.4/10 Very Good! (1,257 reviews)

Dec 20 - Dec 27

7 night stay

Madison (MSN) to Orlando (MCO)

Delta • Non-stop • Coach

Orlando (MCO) to Madison (MSN)

American Airlines • Non-stop • Coach
Price was $1,076, price is now $814 per person
$814
per person
found 1 day ago
The staff was nice, the pool is good, the breakfast has good food. However, it is a old place. What I did not like was the floor of my room. It was dirty. I have kids and their socks was black in few minutes. The floor really needs a deep clean. But the outside area is beautiful.

Reviewed on Jul 14, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9/10 Wonderful! (1,003 reviews)

Jan 12 - Jan 16

4 night stay

Madison (MSN) to Orlando (MCO)

Delta • Non-stop roundtrip • Coach
Price was $1,363, price is now $1,011 per person
$1,011
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.

Reviewed on Oct 7, 2024

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

19.2/10 Exceptional! (487 reviews)

Jan 12 - Jan 16

4 night stay

Madison (MSN) to Orlando (MCO)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,998, price is now $1,546 per person
$1,546
per person
found 1 day ago
Amazing for families visting Orlando.

Reviewed on Oct 24, 2025

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More About Flying To The Villages from Madison

Route Information for Flights from Madison to The Villages

Origin Airport IATA Code
MSN
Destination Airport IATA Code
MCO
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Madison to The Villages

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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.