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$63+ Cheap flights from Madison (MSN) to Orlando (ORL)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — ORL
Jun 14 — Jun 211
Sun 6/14
Sun 6/21
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Orlando are usually found in May or January, booked 65 days in advance, depart on a Wednesday or Saturday and return on a Monday

Cheap flight deals from Madison to Orlando

Cheapest flights from Madison to Orlando
Explore the most affordable flight options available from Madison to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.

This Mytrip deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 pm
MSN
-
MCO
Nonstop2h 52m
Multiple Airlines
Wed 9/28:33 pm
MCO
-
MSN
1 stop23h 36m
Multiple Airlines
Deal found 5/14$186
This Breeze Airways deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:55 pm
MSN
-
MCO
Nonstop2h 52m
Breeze Airways
Wed 5/273:17 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 5/10$188
This Mytrip deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:05 pm
MSN
-
MCO
Nonstop2h 52m
Breeze Airways
Wed 6/33:17 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 5/13$192
This Mytrip deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:55 pm
MSN
-
MCO
Nonstop2h 52m
Breeze Airways
Wed 6/33:17 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 5/12$193
This Booking.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:55 pm
MSN
-
MCO
Nonstop2h 52m
Multiple Airlines
Wed 9/28:33 pm
MCO
-
MSN
1 stop23h 36m
Multiple Airlines
Deal found 5/13$194
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:40 pm
MSN
-
MCO
Nonstop3h 00m
Breeze Airways
Tue 11/101:40 pm
MCO
-
MSN
Nonstop3h 20m
Breeze Airways
Deal found 5/11$197
This Mytrip deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:55 pm
MSN
-
MCO
Nonstop2h 52m
Multiple Airlines
Wed 6/38:33 pm
MCO
-
MSN
1 stop23h 41m
Multiple Airlines
Deal found 5/13$206
This Expedia deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:55 pm
MSN
-
MCO
Nonstop2h 52m
Multiple Airlines
Tue 6/912:52 pm
MCO
-
MSN
1 stop7h 17m
Multiple Airlines
Deal found 5/13$211
This Gotogate deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:55 pm
MSN
-
MCO
Nonstop2h 52m
Breeze Airways
Sat 8/155:07 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 5/13$216

Find flight deals from Madison to Orlando

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Orlando (ORL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$186
(Mytrip)

One-way from

$63
(Booking.com)

Popular in

March

Cheapest in

May

Average price

$252

Good round-trip deal

$188 or less

Good one-way deal

$94 or less
Provider with most accurate pricing for Madison Truax Field-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Orlando (ORL) flights.
Search Deals
From Madison Truax Field to Orlando (ORL)
Search Deals
One-way flight from Madison Truax Field to Orlando (ORL)
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Madison Truax Field to Orlando (ORL).
Search Deals
Price to beat on a one-way flight from Madison Truax Field to Orlando (ORL).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 15, 2026.
Use the filters below to find and compare flights from Madison to Orlando that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 9/5

4:10 pm-12:59 am

2 stops7h 49m

Orlando

Sat 9/12

10:49 am-2:53 pm

1 stop5h 04m

$290
Quickest round-trip

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 6/13

7:55 pm-11:47 pm

Nonstop2h 52m

Orlando

Sat 6/20

5:07 pm-7:15 pm

Nonstop3h 08m

$318

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 9/11

8:10 am-5:56 pm

2 stops8h 46m

Orlando

Tue 9/15

1:00 pm-9:05 pm

2 stops9h 05m

$402

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 8/7

8:10 am-3:03 pm

1 stop5h 53m

Orlando

Fri 8/14

7:40 am-1:42 pm

1 stop7h 02m

$409

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 7/17

8:10 am-4:43 pm

1 stop7h 33m

Orlando

Fri 7/24

4:21 pm-11:12 pm

1 stop7h 51m

$409

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 5/29

5:00 am-11:18 am

1 stop5h 18m

Orlando

Sat 6/6

11:35 am-11:05 pm

2 stops12h 30m

$412

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Thu 7/9

8:10 am-3:03 pm

1 stop5h 53m

Orlando

Fri 7/17

11:35 am-11:12 pm

2 stops12h 37m

$414

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 6/12

3:53 pm-9:55 pm

1 stop5h 02m

Orlando

Mon 6/15

4:26 pm-11:05 pm

1 stop7h 39m

$439

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 5/30

6:29 am-2:11 pm

1 stop6h 42m

Orlando

Wed 6/3

3:05 pm-11:05 pm

2 stops9h 00m

$454
Cheapest one-way

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 7/15

6:00 am-1:40 pm

1 stop6h 40m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Madison to Orlando

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Orlando in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Madison-Orlando flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Orlando flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Orlando flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Orlando flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Orlando flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Orlando

How far ahead should I book a flight from Madison to Orlando?

The price you pay for your flight from Madison to Orlando may vary depending on when you book. For the best chance of a lower fare, look to book 10 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Madison to Orlando?

Currently, May is the cheapest month in which you can book a flight from Madison to Orlando (average of $68). Flying from Madison to Orlando in November is currently the most expensive (average of $172). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to ORL?

Find hourly flight availability from Madison to Orlando. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 15, 2026.

One of the essential ways to save on airfare from Madison to Orlando is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 39% on airfare.

How much does it cost to fly round-trip from Madison to Orlando?

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated May 15, 2026.
Read reviews from past customers who have flown Breeze Airways,Delta, andUnited Airlines from Madison to Orlando. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
284 reviews

Boarding

8.3

Entertainment

6.7

Overall

8.1

Crew

8.7

Comfort

8.2

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.1
Very good
284 reviews
Breeze Airways
8.1
Very good
284 reviews

Boarding

8.3

Entertainment

6.7

Overall

8.1

Crew

8.7

Comfort

8.2

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Delta
7.9
Good
8,453 reviews
Breeze Airways
8.1
Very good
284 reviews

Boarding

8.3

Entertainment

6.7

Overall

8.1

Crew

8.7

Comfort

8.2

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
United Airlines
7.4
Good
9,718 reviews
Breeze Airways
8.1
Very good
284 reviews

Boarding

8.3

Entertainment

6.7

Overall

8.1

Crew

8.7

Comfort

8.2

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,663 reviews
Breeze Airways
8.1
Very good
284 reviews

Boarding

8.3

Entertainment

6.7

Overall

8.1

Crew

8.7

Comfort

8.2

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Frontier
5.7
Fair
2,953 reviews
Breeze Airways
8.1
Very good
284 reviews

Boarding

8.3

Entertainment

6.7

Overall

8.1

Crew

8.7

Comfort

8.2

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Related info for your journey

Find useful and relevant information for your journey from Madison to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Orlando?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Orlando. You should not have trouble finding flights to Orlando from Truax Field; the airport handles an average of 0 outbound flights to Orlando per day. You should also have plenty of airline options to choose from since 5 airlines have flights from the Madison airport to Orlando. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Orlando?

    Airlines like Breeze Airways, Delta, and United Airlines fly from Madison to Orlando in about 2h 52m. The time it takes to get you to your destination can typically vary by up to 4h 41m. The distance from Madison to Orlando is about 1109 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Madison to Orlando round-trip?

    Currently priced at $125, Delta will fly you from Madison to Orlando and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Breeze Airways and Frontier - these airlines can fly you to your destination from $138 and $149, respectively. Users have found that Delta is 61% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Madison to Orlando one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Frontier and American Airlines, as they are both options that can get you from Madison to Orlando for a low price.

  • What are the cheapest flights from Madison to Orlando?

    The cheapest flight price from Madison to Orlando is $78. On average you can expect to pay $174. The most popular route, (Madison Truax Field - Orlando), can usually be booked for $135.

  • Can I find deals for flights from Madison to Orlando that include hotel bookings?

    Yes. In addition to deals on Madison to Orlando flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Orlando?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Orlando.

  • Can I find deals for business class flights from Madison to Orlando?

    Yes. Cheapflights offers flight deals from Madison to Orlando by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Orlando?

    Currently, May is the cheapest month in which you can book a flight from Madison to Orlando (average of $68). Flying from Madison to Orlando in November is currently the most expensive (average of $172). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 5 airlines flying from Madison to Orlando

Discover the top 5 airlines that operate flights from Madison to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$125Average$380FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$138Average$258FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$149Average$318FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$250Average$375FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$251Average$385FlexibilityNo cancel feeOn-time71%

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