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Kissimmee

$40+ Cheap flights from Virginia Beach, VA 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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Cheapflights Tip: The best prices from Virginia Beach to Kissimmee are usually found in September or May, booked 32 days in advance, depart on a Thursday or Tuesday and return on a Thursday

Cheap flight deals from Virginia Beach to Kissimmee

Keep the following information in mind while searching for Virginia Beach to Kissimmee flight deals. Data was last updated January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$77
(Cheapflightsfares)

One-way from

$40
(Frontier)

Popular in

December

Cheapest in

September

Average price

$205
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
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From Virginia Beach to Kissimmee
Search Deals
One-way flight from Virginia Beach to Kissimmee
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Virginia Beach to Kissimmee

Cheapest flights from Virginia Beach to Kissimmee
Explore the most affordable flight options available from Virginia Beach to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/306:45 amORF - MCO
Nonstop2h 12mSpirit Airlines
Fri 2/277:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 1/5$77
This Super.com deal was found by Cheapflights users on 1/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:42 pmORF - MCO
Nonstop2h 16mFrontier
Thu 2/194:22 pmMCO - ORF
Nonstop2h 06mFrontier
Deal found 1/5$78
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/37:33 pmORF - MCO
1 stop4h 26mMultiple Airlines
Tue 2/1010:00 amMCO - ORF
Nonstop2h 05mMultiple Airlines
Deal found 1/6$79
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/101:02 pmORF - MCO
Nonstop2h 16mMultiple Airlines
Sat 2/147:50 pmMCO - ORF
Nonstop2h 00mMultiple Airlines
Deal found 1/5$80
This Priceline deal was found by Cheapflights users on 1/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/249:10 pmORF - MCO
Nonstop2h 15mMultiple Airlines
Fri 1/307:50 pmMCO - ORF
Nonstop2h 00mMultiple Airlines
Deal found 1/5$81
This Super.com deal was found by Cheapflights users on 1/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:18 pmORF - MCO
Nonstop2h 15mFrontier
Mon 2/1610:52 amMCO - ORF
Nonstop2h 05mFrontier
Deal found 1/5$83
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/306:45 amORF - MCO
Nonstop2h 12mSpirit Airlines
Tue 2/39:01 amMCO - ORF
1 stop9h 37mSpirit Airlines
Deal found 1/6$84
This Cheapflightsfares deal was found by Cheapflights users on 1/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/227:33 pmORF - MCO
1 stop4h 26mSpirit Airlines
Thu 1/297:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 1/5$85
This Priceline deal was found by Cheapflights users on 1/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2212:35 pmORF - MCO
Nonstop2h 15mFrontier
Sat 3/2812:24 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 1/6$88
This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:45 amORF - MCO
Nonstop2h 12mSpirit Airlines
Sat 3/77:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 1/6$90

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia Beach 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 January 6, 2026.
Use the filters below to find and compare flights from Virginia Beach to Kissimmee that are best for you.

Fly from

Virginia Beach

Fly to

Kissimmee

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 2/13

3:18 pm-5:33 pm

Nonstop2h 15m

Orlando

Mon 2/16

10:52 am-12:57 pm

Nonstop2h 05m

$99

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 1/16

6:45 am-8:57 am

Nonstop2h 12m

Orlando

Sun 1/18

7:50 pm-9:50 pm

Nonstop2h 00m

$160

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 6/17

6:05 am-8:17 am

Nonstop2h 12m

Orlando

Tue 6/23

9:40 pm-11:39 pm

Nonstop1h 59m

$161

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 2/13

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

Mon 2/16

10:52 am-12:57 pm

Nonstop2h 05m

$168

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 2/20

6:14 pm-12:06 am

1 stop5h 52m

Orlando

Fri 2/27

5:30 am-9:18 am

1 stop3h 48m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 2/1

4:15 pm-6:30 pm

Nonstop2h 15m

Orlando

Sat 2/7

8:45 am-10:40 am

Nonstop1h 55m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 2/23

10:05 am-7:00 pm

2 stops8h 55m

Orlando

Thu 2/26

5:05 pm-11:00 pm

1 stop5h 55m

$186

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 2/17

4:40 pm-9:40 pm

1 stop5h 00m

Orlando

Wed 2/18

8:50 am-4:45 pm

2 stops7h 55m

$205

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/11

6:30 am-12:10 pm

1 stop5h 40m

Orlando

Sun 2/15

9:15 am-11:10 am

Nonstop1h 55m

$244

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 1/19

6:45 am-8:57 am

Nonstop2h 12m

$50

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 18 results
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Best time to book a flight from Virginia Beach to Kissimmee

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

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

Use this chart to determine the optimal time to book a round-trip flight from Virginia Beach to Kissimmee. Price data was last updated on January 2, 2026.

Booking 32 days in advance of your planned departure date is, on average, the best time to get cheap flights from Virginia Beach to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, September is the cheapest month in which you can book a flight from Virginia Beach to Kissimmee (average of $42). Flying from Virginia Beach to Kissimmee in December is currently the most expensive (average of $84). 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 V1B to K1S?

Find hourly flight availability from Virginia Beach 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 January 6, 2026.

A simple way to save on the total cost of your ticket is to fly from Virginia Beach to Kissimmee in the afternoon. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Virginia Beach to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Kissimmee. Price data was last updated on January 3, 2026.

Travelers seeking maximum savings on their Virginia Beach to Kissimmee flight should consider departing on Tuesday afternoons 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.

Weekly flight availability from Virginia Beach to Kissimmee

Explore weekly flight availability from Virginia Beach to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 6, 2026.

The most flights from V1B to K1S are scheduled on a Tuesday (8 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).

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 January 6, 2026.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, and American Airlines from Virginia Beach 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.
Breeze Airways
8.2
Very good
255 reviews

Boarding

8.3

Overall

8.2

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
255 reviews
Breeze Airways
8.2
Very good
255 reviews

Boarding

8.3

Overall

8.2

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
8.0
Very good
4,249 reviews
Breeze Airways
8.2
Very good
255 reviews

Boarding

8.3

Overall

8.2

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,088 reviews
Breeze Airways
8.2
Very good
255 reviews

Boarding

8.3

Overall

8.2

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Spirit Airlines
6.3
Okay
8,283 reviews
Breeze Airways
8.2
Very good
255 reviews

Boarding

8.3

Overall

8.2

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Frontier
5.7
Fair
3,064 reviews
Breeze Airways
8.2
Very good
255 reviews

Boarding

8.3

Overall

8.2

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

Related info for your journey

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

    Airlines like Frontier, Spirit Airlines, and Delta fly from Virginia Beach to Kissimmee in about 2h 12m. The time it takes to get you to your destination can typically vary by up to 3h 40m. Airlines will cover a distance of 655 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $37 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $39 and Breeze Airways from $49 one-way.

  • What are the most reliable airlines from Virginia Beach to Kissimmee?

    Before booking your flight to Kissimmee from Virginia Beach, check out the most reliable airlines to get you to your destination on time: JetBlue (81%), Azul (81%), Spirit Airlines( 63%).

  • What are the cheapest flights from Virginia Beach to Kissimmee?

    Looking at all options, your cheapest flight can be booked for $50. While the most popular route (Norfolk - Orlando) can be booked for $64 on average, our data indicates $220 when flying from Virginia Beach to Kissimmee.

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

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

  • How can I find direct flights from Virginia Beach to Kissimmee?

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

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

    Yes. Cheapflights offers flight deals from Virginia Beach 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 Virginia Beach to Kissimmee?

    Currently, September is the cheapest month in which you can book a flight from Virginia Beach to Kissimmee (average of $42). Flying from Virginia Beach to Kissimmee in December is currently the most expensive (average of $84). 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 9 airlines flying from Virginia Beach to Kissimmee

Discover the top 9 airlines that operate flights from Virginia Beach 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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$47Average$152FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$150FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$75Average$130FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$100Average$220FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$102Average$334FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$117Average$235FlexibilityNo cancel feeOn-time62%
DeltaCheapest$129Average$351FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$353FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$427FlexibilityNo cancel feeOn-time69%

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