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Kissimmee

$84+ Cheap flights from Charlottesville (CHO) to Kissimmee, FL

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — MCO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Charlottesville Albemarle to Kissimmee are usually found in September or February, booked 40 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Find flight deals from Charlottesville to Kissimmee

Cheapest flights from Charlottesville to Kissimmee
Explore the most affordable flight options available from Charlottesville to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:20 pmCHO - MCO
1 stop4h 22mAmerican Airlines
Mon 11/175:00 amMCO - CHO
1 stop4h 55mAmerican Airlines
Deal found 10/27$167
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:03 pmCHO - MCO
1 stop4h 23mAmerican Airlines
Sun 12/145:00 amMCO - CHO
1 stop5h 27mAmerican Airlines
Deal found 10/27$177
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:05 pmCHO - MCO
1 stop6h 45mDelta
Wed 12/248:50 amMCO - CHO
1 stop4h 53mDelta
Deal found 10/28$188
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/84:33 pmCHO - MCO
2 stops7h 11mAmerican Airlines
Wed 12/106:00 amMCO - CHO
1 stop5h 51mAmerican Airlines
Deal found 10/26$208
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:41 pmCHO - MCO
1 stop6h 25mAmerican Airlines
Wed 11/128:00 amMCO - CHO
1 stop5h 53mAmerican Airlines
Deal found 10/26$212
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/107:20 pmCHO - MCO
1 stop4h 22mAmerican Airlines
Fri 11/146:00 amMCO - CHO
1 stop3h 55mAmerican Airlines
Deal found 10/26$227
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:29 amCHO - MCO
1 stop6h 32mDelta
Fri 12/54:33 pmMCO - CHO
1 stop6h 13mDelta
Deal found 10/27$228
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/104:33 pmCHO - MCO
2 stops7h 11mAmerican Airlines
Thu 12/182:53 pmMCO - CHO
1 stop7h 53mAmerican Airlines
Deal found 10/26$232
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1010:22 amCHO - MCO
2 stops7h 21mAmerican Airlines
Sun 12/145:00 amMCO - CHO
1 stop5h 27mAmerican Airlines
Deal found 10/26$242
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:00 amCHO - MCO
1 stop4h 27mAmerican Airlines
Sun 11/165:00 amMCO - CHO
1 stop5h 25mAmerican Airlines
Deal found 10/28$247

Cheap flight deals from Charlottesville to Kissimmee

Keep the following information in mind while searching for Charlottesville to Kissimmee flight deals. Data was last updated October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$167
(American Airlines)

One-way from

$84
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$351
Provider with most accurate pricing for Charlottesville Albemarle-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Charlottesville Albemarle-Orlando (ORL) flights.
Search Deals
From Charlottesville Albemarle to Kissimmee
Search Deals
One-way flight from Charlottesville Albemarle to Kissimmee
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charlottesville to Kissimmee 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 October 28, 2025.
Use the filters below to find and compare flights from Charlottesville to Kissimmee that are best for you.

Fly from

Charlottesville

Fly to

Kissimmee

Route

Depart

Return

Price

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Mon 12/8

5:17 pm-11:44 pm

1 stop6h 27m

Orlando

Wed 12/10

6:00 am-11:51 am

1 stop5h 51m

$167

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Tue 2/3

7:00 am-2:38 pm

1 stop7h 38m

Orlando

Tue 2/10

3:59 pm-10:44 pm

1 stop6h 45m

$177

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Thu 12/11

8:03 pm-12:26 am

1 stop4h 23m

Orlando

Sun 12/14

5:00 am-10:27 am

1 stop5h 27m

$177

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Tue 3/17

3:05 pm-8:38 pm

1 stop5h 33m

Orlando

Wed 3/18

6:00 am-1:52 pm

1 stop7h 52m

$177

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Fri 1/23

7:09 pm-11:45 pm

1 stop4h 36m

Orlando

Mon 1/26

5:00 am-9:59 am

1 stop4h 59m

$187

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Mon 12/15

6:05 pm-12:50 am

1 stop6h 45m

Orlando

Wed 12/24

8:50 am-1:43 pm

1 stop4h 53m

$188

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Tue 1/27

10:24 am-5:35 pm

2 stops7h 11m

Orlando

Sun 2/1

5:00 am-9:59 am

1 stop4h 59m

$208

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Thu 11/13

5:00 am-9:27 am

1 stop4h 27m

Orlando

Sun 11/16

5:00 am-10:25 am

1 stop5h 25m

$247

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Wed 2/4

12:23 pm-7:02 pm

1 stop6h 39m

Orlando

Mon 2/9

5:00 am-9:59 am

1 stop4h 59m

$263

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Tue 3/3

7:17 pm-11:48 pm

1 stop4h 31m

$84

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 14 results
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2

Best time to book a flight from Charlottesville to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Charlottesville 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 Charlottesville to Kissimmee

How far ahead should I book a flight from Charlottesville to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Charlottesville to Kissimmee. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from Charlottesville to Kissimmee, you should look to book at least 40 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Charlottesville to Kissimmee?

Currently, February is the cheapest month in which you can book a flight from Charlottesville to Kissimmee (average of $36). Flying from Charlottesville to Kissimmee in August is currently the most expensive (average of $78). 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 CHO to K1S?

Find hourly flight availability from Charlottesville to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

A simple way to save on the total cost of your ticket is to fly from Charlottesville to Kissimmee in the evening. If you’re flexible enough to do this you can expect to save up to 12% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Charlottesville to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Charlottesville to Kissimmee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Charlottesville to Kissimmee flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated October 28, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Charlottesville to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,994 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Charlottesville to Kissimmee. 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 Charlottesville to Kissimmee?

    Most people fly from Charlottesville Albemarle (CHO) if they book a flight from Charlottesville to Kissimmee. On average, Albemarle has 0 outbound flights to Kissimmee per day from 3 airlines. Charlottesville Albemarle is conveniently located just 7.6 mi from Charlottesville’s city center.

  • How long is the flight from Charlottesville to Kissimmee?

    A quick flight from Charlottesville to Kissimmee can take about 6h 27m. American Airlines provides one of the quickest options available for as low as $167. The distance between Charlottesville and Kissimmee is about 690 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Charlottesville to Kissimmee that include hotel bookings?

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

  • How can I find direct flights from Charlottesville to Kissimmee?

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

  • Can I find deals for business class flights from Charlottesville to Kissimmee?

    Yes. Cheapflights offers flight deals from Charlottesville to Kissimmee 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 Charlottesville to Kissimmee?

    Currently, February is the cheapest month in which you can book a flight from Charlottesville to Kissimmee (average of $36). Flying from Charlottesville to Kissimmee in August is currently the most expensive (average of $78). 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.

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Top 3 airlines flying from Charlottesville to Kissimmee

Discover the top 3 airlines that operate flights from Charlottesville to Kissimmee. 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$196Average$377FlexibilityNo cancel feeOn-time69%
DeltaCheapest$196Average$291FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$384FlexibilityNo cancel feeOn-time71%

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