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Williamsburg

$170+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — RIC
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
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 February 8, 2026.

This American Airlines deal was found by Cheapflights users on 2/7. 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 4/147:02 pm
MCO
-
PHF
1 stop4h 06m
American Airlines
Sun 4/197:59 pm
PHF
-
MCO
1 stop4h 15m
American Airlines
Deal found 2/7$229
This American Airlines deal was found by Cheapflights users on 2/5. 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 2/205:00 am
MCO
-
PHF
1 stop5h 44m
American Airlines
Sun 2/227:55 pm
PHF
-
MCO
1 stop4h 37m
American Airlines
Deal found 2/5$277
This American Airlines deal was found by Cheapflights users on 2/4. 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 2/205:00 am
MCO
-
PHF
1 stop5h 44m
American Airlines
Tue 2/2412:26 pm
PHF
-
MCO
2 stops6h 59m
American Airlines
Deal found 2/4$282
This American Airlines deal was found by Cheapflights users on 2/5. 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 4/67:52 pm
MCO
-
PHF
1 stop4h 07m
American Airlines
Fri 4/107:59 pm
PHF
-
MCO
1 stop4h 15m
American Airlines
Deal found 2/5$291
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Sun 2/87:00 am
MCO
-
PHF
1 stop4h 17m
American Airlines
Tue 2/103:51 pm
PHF
-
MCO
1 stop5h 18m
American Airlines
Deal found 2/5$327
This American Airlines deal was found by Cheapflights users on 2/5. 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 2/75:00 am
MCO
-
PHF
1 stop6h 17m
American Airlines
Sat 2/143:41 pm
PHF
-
MCO
1 stop5h 05m
American Airlines
Deal found 2/5$362
This American Airlines deal was found by Cheapflights users on 2/6. 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 2/216:00 am
MCO
-
PHF
1 stop4h 55m
American Airlines
Wed 2/257:18 pm
PHF
-
MCO
1 stop4h 29m
American Airlines
Deal found 2/6$387
This American Airlines deal was found by Cheapflights users on 2/4. 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 3/216:00 am
MCO
-
PHF
1 stop4h 55m
American Airlines
Sat 3/287:55 pm
PHF
-
MCO
1 stop4h 39m
American Airlines
Deal found 2/4$396

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 February 8, 2026.

Round-trip from

$229
(American Airlines)

One-way from

$170
(American Airlines)

Popular in

January

Cheapest in

November

Average price

$381
From Kissimmee to Williamsburg
Search Deals
One-way flight from Kissimmee to Williamsburg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($11 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 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 February 8, 2026.
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

Tue 4/14

7:02 pm-11:08 pm

1 stop4h 06m

Newport News Intl

Sun 4/19

7:59 pm-12:14 am

1 stop4h 15m

$229

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Fri 2/20

5:00 am-10:44 am

1 stop5h 44m

Newport News Intl

Sun 2/22

7:55 pm-12:32 am

1 stop4h 37m

$277

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Fri 2/20

5:00 am-10:44 am

1 stop5h 44m

Newport News Intl

Tue 2/24

7:18 pm-11:47 pm

1 stop4h 29m

$277

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Sat 2/21

6:00 am-10:55 am

1 stop4h 55m

Newport News Intl

Wed 2/25

12:26 pm-10:00 pm

2 stops9h 34m

$282

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Mon 4/6

7:52 pm-11:59 pm

1 stop4h 07m

Newport News Intl

Fri 4/10

7:59 pm-12:14 am

1 stop4h 15m

$291

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Sat 3/21

6:00 am-10:55 am

1 stop4h 55m

Newport News Intl

Sat 3/28

7:55 pm-12:34 am

1 stop4h 39m

$396

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Sat 5/30

5:31 pm-12:25 am

1 stop6h 54m

Newport News Intl

Sat 6/6

8:00 pm-12:10 am

1 stop4h 10m

$459

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Sun 5/10

6:42 pm-11:59 pm

1 stop5h 17m

$298

OrlandoNewport News

MCO - PHF

MCOPHF

Orlando

Sat 5/9

3:50 pm-11:59 pm

2 stops8h 09m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

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, July is the cheapest month in which you can book a flight from Kissimmee to Williamsburg (average of $43). 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 February 8, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 19% on flights from Kissimmee to Williamsburg by exploring options for tickets in the evening.

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 January 31, 2026.

Travelers seeking maximum savings on their Kissimmee to Williamsburg flight should consider departing on Monday mornings 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 February 8, 2026.
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
11,248 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Boarding

7.5

Food

6.4

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,248 reviews
American Airlines
7.2
Good
11,248 reviews

Crew

8.0

Entertainment

6.9

Comfort

7.2

Boarding

7.5

Food

6.4

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 06m. American Airlines provides one of the quickest options available for as low as $229. 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 Spirit Airlines (73%), Azul (71%) or JetBlue (66%) 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 $49. On average you can expect to pay $130. The most popular route, (Orlando - Newport News Intl), can usually be booked for $229.

  • 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, July is the cheapest month in which you can book a flight from Kissimmee to Williamsburg (average of $43). 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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$43Average$123FlexibilityNo cancel feeOn-time65%
FrontierCheapest$49Average$130FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$73Average$118FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$79Average$190FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$79Average$298FlexibilityNo cancel feeOn-time63%
DeltaCheapest$88Average$321FlexibilityNo cancel feeOn-timeN/A
Breeze AirwaysCheapest$100Average$168FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$162Average$376FlexibilityNo cancel feeOn-time71%

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