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Kissimmee

$80+ 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
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This American Airlines deal was found by Cheapflights users on 2/2. 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 3/117:57 pm
CHO
-
MCO
1 stop4h 37m
American Airlines
Tue 3/1711:52 am
MCO
-
CHO
1 stop6h 09m
American Airlines
Deal found 2/2$159
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/217:57 pm
CHO
-
MCO
1 stop4h 35m
American Airlines
Tue 2/248:25 am
MCO
-
CHO
1 stop5h 14m
American Airlines
Deal found 2/2$163
This American Airlines deal was found by Cheapflights users on 2/2. 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 4/258:03 pm
CHO
-
MCO
1 stop4h 11m
American Airlines
Tue 4/286:00 am
MCO
-
CHO
1 stop3h 54m
American Airlines
Deal found 2/2$173
This Delta deal was found by Cheapflights users on 2/1. 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 3/96:06 pm
CHO
-
MCO
1 stop4h 56m
Delta
Wed 3/189:00 am
MCO
-
CHO
1 stop4h 46m
Delta
Deal found 2/1$177
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/25:00 pm
CHO
-
MCO
2 stops7h 32m
American Airlines
Tue 3/37:00 am
MCO
-
CHO
1 stop6h 39m
American Airlines
Deal found 1/31$183
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/167:57 pm
CHO
-
MCO
1 stop4h 35m
American Airlines
Wed 2/186:00 am
MCO
-
CHO
2 stops7h 39m
American Airlines
Deal found 2/1$187
This Delta deal was found by Cheapflights users on 2/1. 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 3/92:15 pm
CHO
-
MCO
1 stop8h 28m
Delta
Tue 3/173:55 pm
MCO
-
CHO
1 stop6h 42m
Delta
Deal found 2/1$198
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/188:29 pm
CHO
-
MCO
1 stop4h 04m
United Airlines
Mon 3/236:08 pm
MCO
-
CHO
1 stop6h 01m
United Airlines
Deal found 2/2$217

Find flight deals from Charlottesville to Kissimmee

Keep the following information in mind while searching for Charlottesville to Kissimmee flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$159
(American Airlines)

One-way from

$80
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$327
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. 22% potential increase in price ($117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 3, 2026.
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

Wed 3/11

7:57 pm-12:34 am

1 stop4h 37m

Orlando

Tue 3/17

11:52 am-6:01 pm

1 stop6h 09m

$159

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Mon 3/2

5:28 pm-9:58 pm

1 stop4h 30m

Orlando

Tue 3/3

7:00 am-1:49 pm

1 stop6h 49m

$177

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Wed 3/11

11:54 am-5:22 pm

1 stop5h 28m

Orlando

Wed 3/18

7:00 am-1:46 pm

1 stop6h 46m

$177

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Fri 2/20

2:34 pm-9:05 pm

1 stop6h 31m

Orlando

Mon 2/23

5:30 pm-10:49 pm

1 stop5h 19m

$198

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Sat 2/21

4:00 pm-9:58 pm

1 stop5h 58m

Orlando

Mon 2/23

5:30 pm-10:49 pm

1 stop5h 19m

$198

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Fri 5/15

8:23 pm-12:59 am

1 stop4h 36m

Orlando

Sun 5/24

5:55 pm-12:26 am

1 stop6h 31m

$217

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Wed 3/18

8:29 pm-12:33 am

1 stop4h 04m

Orlando

Mon 3/23

6:08 pm-12:09 am

1 stop6h 01m

$217

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Wed 3/11

2:15 pm-8:50 pm

1 stop6h 35m

Orlando

Mon 3/16

5:30 am-11:13 am

1 stop5h 43m

$218

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Tue 3/10

11:54 am-4:17 pm

1 stop4h 23m

Orlando

Mon 3/16

5:30 am-11:13 am

1 stop5h 43m

$218

CharlottesvilleOrlando

CHO - MCO

CHOMCO

Charlottesville Albemarle

Mon 3/9

6:06 pm-12:06 am

1 stop6h 00m

Orlando

Thu 3/12

7:00 am-1:35 pm

1 stop6h 35m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 17 results
1
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 January 30, 2026.

To ensure you get the cheapest price possible for a flight from Charlottesville to Kissimmee, you should look to book at least 19 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, December is the cheapest month in which you can book a flight from Charlottesville to Kissimmee (average of $40). 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.

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 February 3, 2026.
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
8,132 reviews

Entertainment

7.8

Boarding

8.1

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

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
8,132 reviews
Delta
7.9
Good
8,132 reviews

Entertainment

7.8

Boarding

8.1

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

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
9,229 reviews
Delta
7.9
Good
8,132 reviews

Entertainment

7.8

Boarding

8.1

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

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
11,212 reviews
Delta
7.9
Good
8,132 reviews

Entertainment

7.8

Boarding

8.1

Overall

7.9

Food

7.2

Comfort

7.9

Crew

8.5

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 4h 30m. American Airlines provides one of the quickest options available for as low as $177. The distance between Charlottesville and Kissimmee is about 690 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Charlottesville to Kissimmee one-way?

    $79 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $88 and $92, respectively.

  • 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, December is the cheapest month in which you can book a flight from Charlottesville to Kissimmee (average of $40). 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.

See more FAQs

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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$183Average$386FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$196Average$381FlexibilityNo cancel feeOn-time69%

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