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Kissimmee

$39+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chesapeake to Kissimmee are usually found in February or March, booked 64 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap flight deals from Chesapeake to Kissimmee

Keep the following information in mind while searching for Chesapeake to Kissimmee flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$92
(Kiwi.com)

One-way from

$39
(Booking.com)

Popular in

October

Cheapest in

February

Average price

$194
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
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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. 8% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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.
Sat 3/89:05 amORF - MCO
Nonstop2h 14mMultiple Airlines
Fri 3/145:24 pmMCO - ORF
Nonstop2h 03mMultiple Airlines
Deal found 2/19$92
This Frontier deal was found by Cheapflights users on 2/19. 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.
Sun 3/96:38 pmORF - MCO
Nonstop2h 18mFrontier
Sat 3/156:11 amMCO - ORF
Nonstop2h 04mFrontier
Deal found 2/19$93
This eDestinos deal was found by Cheapflights users on 2/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/58:32 pmORF - MCO
Nonstop2h 14mSpirit Airlines
Thu 3/65:55 amMCO - ORF
1 stop4h 35mSpirit Airlines
Deal found 2/18$95

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 February 20, 2025.

Fly from

Chesapeake

Fly to

Kissimmee

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 3/8

9:05 am-11:19 am

Nonstop2h 14m

Orlando

Fri 3/14

5:24 pm-7:27 pm

Nonstop2h 03m

$92

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 3/9

6:38 pm-8:56 pm

Nonstop2h 18m

Orlando

Sat 3/15

6:11 am-8:15 am

Nonstop2h 04m

$93

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 3/5

8:32 pm-10:46 pm

Nonstop2h 14m

Orlando

Thu 3/6

5:55 am-10:30 am

1 stop4h 35m

$95

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 3/5

4:19 pm-8:39 pm

1 stop4h 20m

Orlando

Thu 3/6

6:15 am-12:11 pm

1 stop5h 56m

$277

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 2/25

7:00 am-9:16 am

Nonstop2h 16m

$39

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 3/1

7:16 pm-9:35 pm

Nonstop2h 19m

$48

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 3/2

4:05 pm-3:35 pm

1 stop23h 30m

$73

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 5/20

6:00 pm-12:06 am

1 stop6h 06m

$95

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 3/9

4:05 pm-7:19 am

3 stops39h 14m

$116

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 3/19

6:32 am-2:20 pm

1 stop7h 48m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February 14, 2025.

The best time to book flights from Chesapeake to Kissimmee is 64 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 February 20, 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 February 16, 2025.

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

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 February 20, 2025.
To help decide which airline to fly from Chesapeake to Kissimmee, see what other customers have to say about Southwest, Breeze Airways and Delta. 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
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Breeze Airways
8.1
Very good
150 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 ($39), Frontier ($48), 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 (82%), Azul (74%) or JetBlue (74%) 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 $57. While the most popular route (Norfolk - Orlando) can be booked for $61 on average our data indicates $195 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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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$139FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$45Average$139FlexibilityNo cancel feeOn-time88%
FrontierCheapest$48Average$165FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$107Average$192FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$118Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$133Average$403FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$334FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$349FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$207Average$374FlexibilityNo cancel feeOn-time63%
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