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Kissimmee

$48+ Cheap flights from Chesapeake, 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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The best prices from Chesapeake to Kissimmee are usually found in February or January, booked 43 days in advance, depart on a Tuesday or Saturday and return on a Thursday

Cheap flight deals from Chesapeake to Kissimmee

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Kissimmee (K1S). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$83
(Frontier)

One-way from

$48
(Cheapflightsfares)

Popular in

November

Cheapest in

February

Average price

$173
From Chesapeake to Kissimmee
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One-way flight from Chesapeake to Kissimmee
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Highest demand for flights based on searches. 16% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Find flight deals from Chesapeake to Kissimmee

Cheapest flights from Chesapeake to Kissimmee
Explore the most affordable flight options available from Chesapeake to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 21, 2025.

This Frontier deal was found by Cheapflights users on 1/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/17:16 pmORF - MCO
Nonstop2h 19mFrontier
mar. 3/43:28 pmMCO - ORF
Nonstop2h 06mFrontier
Deal found 1/21$83
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
lun. 2/247:00 amORF - MCO
Nonstop2h 16mMultiple Airlines
jue. 2/2711:10 amMCO - ORF
Nonstop2h 05mMultiple Airlines
Deal found 1/21$87
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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.
jue. 1/305:25 amORF - MCO
Nonstop2h 10mSpirit Airlines
sáb. 2/16:12 pmMCO - ORF
Nonstop2h 03mSpirit Airlines
Deal found 1/21$95
This United Airlines deal was found by Cheapflights users on 1/21. 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.
sáb. 3/18:00 pmORF - MCO
1 stop4h 30mUnited Airlines
mar. 3/45:24 pmMCO - ORF
1 stop6h 02mUnited Airlines
Deal found 1/21$237
This Southwest deal was found by Cheapflights users on 1/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/1112:55 pmORF - MCO
Nonstop2h 10mSouthwest
dom. 2/168:00 amMCO - ORF
2 stops7h 25mSouthwest
Deal found 1/20$257

Find flights from Chesapeake to Kissimmee within your budget

Customize your flight search to find flights from Chesapeake 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 enero 21, 2025.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

dom. 2/16

6:12 pm-8:30 pm

Nonstop2h 18m

Orlando

jue. 2/20

11:10 am-1:15 pm

Nonstop2h 05m

$87

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 2/10

5:25 am-7:35 am

Nonstop2h 10m

Orlando

jue. 2/13

11:10 am-1:15 pm

Nonstop2h 05m

$89

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

dom. 2/2

5:25 am-7:35 am

Nonstop2h 10m

Orlando

mié. 2/5

6:09 am-3:36 pm

1 stop9h 27m

$96

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

sáb. 3/1

8:00 pm-12:30 am

1 stop4h 30m

Orlando

mar. 3/4

4:20 pm-11:36 pm

1 stop7h 16m

$237

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mar. 2/11

12:55 pm-3:05 pm

Nonstop2h 10m

Orlando

dom. 2/16

8:00 am-3:25 pm

2 stops7h 25m

$257

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

dom. 2/16

6:10 pm-12:31 am

1 stop6h 21m

Orlando

jue. 2/20

6:03 am-10:17 am

1 stop4h 14m

$262

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 1/27

5:25 am-7:35 am

Nonstop2h 10m

$48

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

dom. 3/23

7:11 pm-9:30 pm

Nonstop2h 19m

$52

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

jue. 2/6

3:00 pm-9:10 pm

1 stop6h 10m

$73

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

jue. 2/6

12:51 pm-9:03 pm

2 stops8h 12m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 13 results
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Best time to book a flight from Chesapeake to Kissimmee

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

Travel insights for flights from Chesapeake to Kissimmee

Get recent, data-driven insights about flights from Chesapeake to Kissimmee including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Kissimmee. Price data was last updated on January 17, 2025.

The best time to book flights from Chesapeake 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 Chesapeake to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Chesapeake to Kissimmee (average of $206). Flying from Chesapeake to Kissimmee in November is currently the most expensive (average of $289). 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 C6E to K1S?

Find hourly flight availability from Chesapeake 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 enero 21, 2025.

When flying from Chesapeake to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

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

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

Weekly flight availability from Chesapeake to Kissimmee

Explore weekly flight availability from Chesapeake 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 enero 21, 2025.

The most flights from C6E to K1S are scheduled on a Monday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (4 on average).

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 enero 21, 2025.
To help decide which airline to fly from Chesapeake to Kissimmee, see what other customers have to say about Spirit Airlines, Frontier and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Breeze Airways
8.1
Very good
143 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

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

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

    The cheapest airlines for a one-way flight from Chesapeake to Kissimmee are Spirit Airlines ($48), Frontier ($52), and Breeze Airways ($73).

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

    No one likes to see their flight delayed. When booking a flight from Chesapeake to Kissimmee consider choosing Spirit Airlines (72%), Azul (63%) or JetBlue (63%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chesapeake to Kissimmee?

    Looking at all options, your cheapest flight can be booked for $70. While the most popular route (Norfolk - Orlando) can be booked for $88 on average our data indicates $196 when flying from Chesapeake to Kissimmee.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Chesapeake to Kissimmee (average of $206). Flying from Chesapeake to Kissimmee in November is currently the most expensive (average of $289). 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.

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Chesapeake to Kissimmee

Discover the top 9 airlines that operate flights from Chesapeake 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$127FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$45Average$139FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$59Average$252FlexibilityNo cancel feeOn-time62%
FrontierCheapest$78Average$164FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$102Average$200FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$133Average$433FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$330FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$341FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$207Average$367FlexibilityNo cancel feeOn-time63%
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