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Kissimmee

$74+ Cheap flights from Charleston, WV (CRW) 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
CRW — MCO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Charleston Yeager to Kissimmee are usually found in July or January, booked 43 days in advance, depart on a Monday or Thursday and return on a Monday

Cheap flight deals from Charleston to Kissimmee

Keep the following information in mind while searching for Charleston 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

$138
(Breeze Airways)

One-way from

$74
(Breeze Airways)

Popular in

February

Cheapest in

July

Average price

$338
Provider with most accurate pricing for Charleston Yeager-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Charleston Yeager-Orlando (ORL) flights.
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From Charleston Yeager to Kissimmee
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One-way flight from Charleston Yeager to Kissimmee
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Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Charleston to Kissimmee

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

This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/212:43 pmCRW - MCO
Nonstop2h 09mBreeze Airways
Thu 12/257:05 amMCO - CRW
Nonstop2h 13mBreeze Airways
Deal found 10/26$142
This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/212:43 pmCRW - MCO
Nonstop2h 09mBreeze Airways
Sun 12/287:05 amMCO - CRW
Nonstop2h 13mBreeze Airways
Deal found 10/28$168
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:43 pmCRW - MCO
Nonstop2h 09mBreeze Airways
Sun 12/287:05 amMCO - CRW
Nonstop2h 13mBreeze Airways
Deal found 10/26$203
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/302:43 pmCRW - MCO
Nonstop2h 09mBreeze Airways
Thu 11/67:05 amMCO - CRW
Nonstop2h 13mBreeze Airways
Deal found 10/26$223
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Tue 11/117:06 pmCRW - MCO
1 stop4h 36mAmerican Airlines
Sat 11/158:05 amMCO - CRW
1 stop4h 34mAmerican Airlines
Deal found 10/25$232
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/302:43 pmCRW - MCO
Nonstop2h 09mBreeze Airways
Sun 11/27:05 amMCO - CRW
Nonstop2h 13mBreeze Airways
Deal found 10/26$236
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.
Sat 12/61:08 pmCRW - MCO
1 stop4h 34mAmerican Airlines
Sat 12/136:01 amMCO - CRW
1 stop4h 46mAmerican Airlines
Deal found 10/27$238
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/121:59 pmCRW - MCO
1 stop7h 48mUnited Airlines
Tue 11/189:40 amMCO - CRW
1 stop7h 30mUnited Airlines
Deal found 10/28$243
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.
Fri 12/57:10 pmCRW - MCO
1 stop4h 34mAmerican Airlines
Wed 12/103:17 pmMCO - CRW
2 stops7h 37mAmerican Airlines
Deal found 10/27$244

Cheapflights Fare Finder

 
Customize your flight search to find flights from Charleston 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 Charleston to Kissimmee that are best for you.

Fly from

Charleston

Fly to

Kissimmee

Route

Depart

Return

Price

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Sun 12/21

2:43 pm-4:52 pm

Nonstop2h 09m

Orlando

Thu 12/25

7:05 am-9:18 am

Nonstop2h 13m

$142

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Sun 12/21

2:43 pm-4:52 pm

Nonstop2h 09m

Orlando

Sun 12/28

7:05 am-9:18 am

Nonstop2h 13m

$168

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Fri 1/9

5:49 am-3:37 pm

2 stops9h 48m

Orlando

Fri 1/16

5:00 am-11:54 am

1 stop6h 54m

$220

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Tue 11/11

7:06 pm-11:42 pm

1 stop4h 36m

Orlando

Sat 11/15

8:05 am-12:39 pm

1 stop4h 34m

$232

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Wed 12/10

3:49 pm-10:50 pm

1 stop7h 01m

Orlando

Tue 12/16

4:33 pm-10:49 pm

1 stop6h 16m

$238

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Sat 12/6

1:08 pm-5:42 pm

1 stop4h 34m

Orlando

Sat 12/13

6:01 am-10:47 am

1 stop4h 46m

$238

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Wed 11/12

1:59 pm-9:47 pm

1 stop7h 48m

Orlando

Tue 11/18

9:40 am-5:10 pm

1 stop7h 30m

$243

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Mon 11/3

3:51 pm-10:59 pm

2 stops7h 08m

Orlando

Mon 11/10

5:00 am-11:50 am

1 stop6h 50m

$284

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Sun 12/21

9:58 am-8:08 pm

1 stop10h 10m

Orlando

Thu 12/25

7:05 am-9:18 am

Nonstop2h 13m

$317

CharlestonOrlando

CRW - MCO

CRWMCO

Charleston Yeager

Wed 12/10

3:49 pm-10:50 pm

1 stop7h 01m

$120

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 20 results
1
2

Best time to book a flight from Charleston to Kissimmee

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

How far ahead should I book a flight from Charleston, West Virginia to Kissimmee?

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

The best time to book flights from Charleston, West Virginia to Kissimmee is 43 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Charleston, West Virginia to Kissimmee?

Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Kissimmee (average of $76). Flying from Charleston, West Virginia to Kissimmee in November is currently the most expensive (average of $130). 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 CRW to K1S?

Find hourly flight availability from Charleston 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.

One of the essential ways to save on airfare from Charleston, West Virginia to Kissimmee is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 65% on airfare.

What is the cheapest day to fly from Charleston, West Virginia to Kissimmee?

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

Travelers seeking maximum savings on their Charleston, West Virginia to Kissimmee flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday mornings 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.
Read through reviews of airlines operating flights from Charleston to Kissimmee, such as Breeze Airways, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.7

Comfort

8.1

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
220 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.7

Comfort

8.1

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
7.9
Good
7,995 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.7

Comfort

8.1

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
United Airlines
7.4
Good
8,996 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.7

Comfort

8.1

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,033 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.7

Comfort

8.1

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

Related info for your journey

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

    For a flight from Charleston to Kissimmee, you will be flying from Yeager. Charleston Yeager (CRW) is just 2.7 mi from the center of the city. Yeager is the only Charleston airport and it handles 0 outbound flights to Kissimmee per day. 4 airlines have flights to Kissimmee from Charleston Yeager on a regular basis.

  • How long is the flight from Charleston, West Virginia to Kissimmee?

    A quick flight from Charleston, West Virginia to Kissimmee can take about 2h 09m. Breeze Airways provides one of the quickest options available for as low as $142. The distance from Charleston, West Virginia to Kissimmee is about 687 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Charleston, West Virginia to Kissimmee?

    On average you can expect to pay $155 for a flight from Charleston, West Virginia to Kissimmee. The cheapest flight overall is $82 while the most popular route, (Charleston Yeager - Orlando) is currently priced at $142.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Charleston 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 Charleston, West Virginia to Kissimmee?

    Currently, December is the cheapest month in which you can book a flight from Charleston, West Virginia to Kissimmee (average of $76). Flying from Charleston, West Virginia to Kissimmee in November is currently the most expensive (average of $130). 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 4 airlines flying from Charleston to Kissimmee

Discover the top 4 airlines that operate flights from Charleston 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
Breeze AirwaysCheapest$99Average$171FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$186Average$333FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$214Average$380FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$263Average$308FlexibilityNo cancel feeOn-time69%

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