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$144+ Cheap flights from Kissimmee, FL to Williamsburg, VA

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — RIC
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Kissimmee to Williamsburg

Cheapest flights from Kissimmee to Williamsburg
Explore the most affordable flight options available from Kissimmee to Williamsburg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 12/236:00 amMCO - PHF
1 stop4h 54mAmerican Airlines
Tue 12/305:00 amPHF - MCO
1 stop4h 40mAmerican Airlines
Deal found 12/16$292
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/205:00 amMCO - PHF
1 stop5h 54mAmerican Airlines
Mon 12/225:00 amPHF - MCO
1 stop4h 40mAmerican Airlines
Deal found 12/16$327
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/185:31 pmMCO - PHF
1 stop6h 28mAmerican Airlines
Mon 12/225:00 amPHF - MCO
1 stop4h 40mAmerican Airlines
Deal found 12/15$342
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/161:00 pmMCO - PHF
1 stop5h 50mAmerican Airlines
Mon 12/228:03 pmPHF - MCO
1 stop4h 26mAmerican Airlines
Deal found 12/15$347
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/187:55 pmMCO - PHF
1 stop4h 04mAmerican Airlines
Sun 12/218:03 pmPHF - MCO
1 stop4h 26mAmerican Airlines
Deal found 12/15$397
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/1611:45 amMCO - PHF
1 stop7h 05mAmerican Airlines
Sun 12/218:03 pmPHF - MCO
1 stop4h 26mAmerican Airlines
Deal found 12/15$402
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/185:00 amMCO - PHF
1 stop5h 54mAmerican Airlines
Wed 12/245:00 amPHF - MCO
1 stop4h 40mAmerican Airlines
Deal found 12/15$417
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/166:00 amMCO - PHF
1 stop4h 57mAmerican Airlines
Wed 12/245:00 amPHF - MCO
1 stop4h 40mAmerican Airlines
Deal found 12/15$422

Find flight deals from Kissimmee to Williamsburg

Keep the following information in mind while searching for Kissimmee to Williamsburg flight deals. Data was last updated December 18, 2025.

Round-trip from

$164
(American Airlines)

One-way from

$144
(American Airlines)

Popular in

January

Cheapest in

November

Average price

$271
From Kissimmee to Williamsburg
Search Deals
One-way flight from Kissimmee to Williamsburg
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Williamsburg 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 December 18, 2025.
Use the filters below to find and compare flights from Kissimmee to Williamsburg that are best for you.

Fly from

Kissimmee

Fly to

Williamsburg

Route

Depart

Return

Price

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Wed 1/7

7:00 am-11:17 am

1 stop4h 17m

Newport News Intl

Wed 1/14

4:26 pm-11:59 pm

2 stops7h 33m

$164

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Thu 1/1

7:55 pm-11:59 pm

1 stop4h 04m

Newport News Intl

Mon 1/5

8:03 pm-12:29 am

1 stop4h 26m

$267

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Tue 12/23

6:00 am-10:54 am

1 stop4h 54m

Newport News Intl

Tue 12/30

5:00 am-9:40 am

1 stop4h 40m

$292

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Tue 12/23

6:00 am-10:54 am

1 stop4h 54m

Newport News Intl

Sat 12/27

8:03 pm-12:51 am

1 stop4h 48m

$424

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Mon 12/22

5:00 am-10:54 am

1 stop5h 54m

Newport News Intl

Tue 12/23

5:00 am-9:40 am

1 stop4h 40m

$442

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Fri 1/2

6:00 am-10:54 am

1 stop4h 54m

Newport News Intl

Sun 1/4

8:03 pm-12:29 am

1 stop4h 26m

$466

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Thu 12/25

2:04 pm-7:33 pm

1 stop5h 29m

$144

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Wed 12/24

2:04 pm-7:33 pm

1 stop5h 29m

$144

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Mon 12/29

6:00 am-10:54 am

1 stop4h 54m

$144

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Tue 12/23

5:00 am-10:54 am

1 stop5h 54m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 14 results
1
2

Best time to book a flight from Kissimmee to Williamsburg

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

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

Currently, January is the cheapest month in which you can book a flight from Kissimmee to Williamsburg (average of $38). Flying from Kissimmee to Williamsburg in June is currently the most expensive (average of $87). 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 K1S to W11?

Find hourly flight availability from Kissimmee to Williamsburg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 36% on flights from Kissimmee to Williamsburg by exploring options for tickets in the afternoon.

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

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

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

Reviews of airlines servicing Williamsburg

Get insights into the airlines that provide service to Williamsburg. 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 Williamsburg. Reviews last updated December 18, 2025.
Read through reviews of airlines operating flights from Kissimmee to Williamsburg, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

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

  • How long is the flight from Kissimmee to Williamsburg?

    A quick flight from Kissimmee to Williamsburg can take about 4h 17m. American Airlines provides one of the quickest options available for as low as $164. Airlines will cover a distance of 662 mi.

  • What are the most reliable airlines from Kissimmee to Williamsburg?

    No one likes to see their flight delayed. When booking a flight from Kissimmee to Williamsburg consider choosing Azul (90%), Spirit Airlines (87%) or JetBlue (85%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Kissimmee to Williamsburg?

    The cheapest flight price from Kissimmee to Williamsburg is $40. On average you can expect to pay $149. The most popular route, (Orlando - Newport News Intl), can usually be booked for $164.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Kissimmee to Williamsburg (average of $38). Flying from Kissimmee to Williamsburg in June is currently the most expensive (average of $87). 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 8 airlines flying from Kissimmee to Williamsburg

Discover the top 8 airlines that operate flights from Kissimmee to Williamsburg. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$48Average$144FlexibilityNo cancel feeOn-time65%
FrontierCheapest$51Average$131FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$73Average$119FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$79Average$299FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$83Average$198FlexibilityNo cancel feeOn-time62%
DeltaCheapest$88Average$302FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$103Average$200FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$389FlexibilityNo cancel feeOn-time71%

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