Kissimmee

$41+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Nov 10 — Nov 171
1 adult
Sun 11/10
Sun 11/17
We work with more than 300 partners to bring you better travel deals

...and more

Find cheap flights from Chesapeake to Kissimmee with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Chesapeake to Kissimmee are usually found in February or January, booked 44 days in advance, depart on a Saturday or Tuesday and return on a Saturday

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 November 5, 2024.

Popular in

August

Cheapest in

February

Round-trip from

$86
(FlightHub)

One-way from

$41
(eDestinos)
High demand for flights, 26% potential price rise
Best time to find cheap flights, 44% potential price drop
From Chesapeake to Kissimmee
One-way flight from Chesapeake to Kissimmee

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 November 5, 2024.

This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/169:54 amORF - MCO
1 stop14h 17mFrontier
Tue 12/1710:40 amMCO - ORF
Nonstop2h 02mFrontier
Deal found 11/4$123
This FareScan deal was found by Cheapflights users on 11/4. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/158:06 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Sat 11/235:30 amMCO - ORF
1 stop17h 25mSpirit Airlines
Deal found 11/4$126
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/217:00 pmORF - MCO
Nonstop2h 11mMultiple Airlines
Sun 11/245:10 amMCO - ORF
1 stop10h 57mMultiple Airlines
Deal found 11/4$140
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/32:48 pmORF - MCO
2 stops10h 01mUnited Airlines
Thu 12/58:00 amMCO - ORF
1 stop5h 57mUnited Airlines
Deal found 11/5$301
This Mytrip deal was found by Cheapflights users on 11/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/108:00 amORF - MCO
1 stop11h 35mBreeze Airways
Wed 11/136:41 pmMCO - ORF
1 stop13h 57mBreeze Airways
Deal found 11/4$313
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/246:56 amORF - MCO
1 stop4h 44mDelta
Tue 12/35:00 pmMCO - ORF
1 stop4h 53mDelta
Deal found 11/4$315

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/22

9:01 pm-11:18 pm

Nonstop2h 17m

$72

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/8

9:19 pm-11:31 pm

Nonstop2h 12m

$74

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 11/21

8:23 pm-12:25 pm

2 stops16h 02m

$81

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/7

2:00 pm-8:51 pm

1 stop6h 51m

$113

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/8

6:09 pm-11:34 pm

1 stop5h 25m

$143

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 12/9

2:45 pm-12:49 am

2 stops10h 04m

$153

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 11/21

8:00 am-12:21 am

3 stops16h 21m

$162

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/8

4:30 pm-11:55 pm

2 stops7h 25m

$196

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 12/16

9:54 am-12:11 am

1 stop14h 17m

Orlando

Tue 12/17

10:40 am-12:42 pm

Nonstop2h 02m

$123

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 11/15

8:06 pm-10:16 pm

Nonstop2h 10m

Orlando

Sat 11/23

5:30 am-10:55 pm

1 stop17h 25m

$126

Flights are sorted by cheapest first

Deals found on 11/4

Showing 1-10 of 12 results
1
2

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 November 1, 2024.

The best time to book flights from Chesapeake to Kissimmee is 44 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, December is the cheapest month in which you can book a flight from Chesapeake to Kissimmee (average of $203). Flying from Chesapeake to Kissimmee in November is currently the most expensive (average of $263). 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 November 5, 2024.

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 November 3, 2024.

Travelers seeking maximum savings on their Chesapeake to Kissimmee flight should consider departing on Tuesday mornings 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.

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 November 5, 2024.
To help decide which airline to fly from Chesapeake to Kissimmee, see what other customers have to say about Spirit Airlines and Frontier. 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.
8.2
Very good
118 reviews

Food

6.8

Entertainment

6.6

Overall

8.2

Crew

9.0

Comfort

8.3

Boarding

8.4

Reviews

1 / 8

Good flight on Breeze, on time, comfortable, friendly pilot and crew

8.2
Very good
118 reviews
8.2
Very good
118 reviews

Food

6.8

Entertainment

6.6

Overall

8.2

Crew

9.0

Comfort

8.3

Boarding

8.4

Reviews

1 / 8

Good flight on Breeze, on time, comfortable, friendly pilot and crew

8.1
Very good
5,082 reviews
8.2
Very good
118 reviews

Food

6.8

Entertainment

6.6

Overall

8.2

Crew

9.0

Comfort

8.3

Boarding

8.4

Reviews

1 / 8

Good flight on Breeze, on time, comfortable, friendly pilot and crew

8.0
Very good
8,830 reviews
8.2
Very good
118 reviews

Food

6.8

Entertainment

6.6

Overall

8.2

Crew

9.0

Comfort

8.3

Boarding

8.4

Reviews

1 / 8

Good flight on Breeze, on time, comfortable, friendly pilot and crew

7.4
Good
9,215 reviews
8.2
Very good
118 reviews

Food

6.8

Entertainment

6.6

Overall

8.2

Crew

9.0

Comfort

8.3

Boarding

8.4

Reviews

1 / 8

Good flight on Breeze, on time, comfortable, friendly pilot and crew

7.2
Good
10,000 reviews
8.2
Very good
118 reviews

Food

6.8

Entertainment

6.6

Overall

8.2

Crew

9.0

Comfort

8.3

Boarding

8.4

Reviews

1 / 8

Good flight on Breeze, on time, comfortable, friendly pilot and crew

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.
  • Can I find flights from Chesapeake to Kissimmee for under $100 on Cheapflights?

    Yes, there are multiple flights from Chesapeake to Kissimmee for under $100. The cheapest flight booked recently is on Spirit Airlines for just $86, but on average you can expect to pay $87.

  • Are there nonstop flights from Chesapeake to Kissimmee for under $100 on Cheapflights?

    Cheapflights has at least 4 direct flights from Chesapeake to Kissimmee under $100. A good price for a nonstop flight from Chesapeake to Kissimmee is less than $168.

  • Are there last-minute flights available from Chesapeake to Kissimmee for under $200?

    There are currently 5+ open flights from Chesapeake to Kissimmee within the next 7 days for less than $200.

  • 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 ($41), Frontier ($64), and Breeze Airways ($81).

  • 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 (100%), Azul (95%) or JetBlue (94%) 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 $67. While the most popular route (Norfolk - Orlando) can be booked for $87 on average our data indicates $188 when flying from Chesapeake to Kissimmee.

  • What does RIC to MCO mean?

    RIC stands for Richmond Byrd Intl Airport, while MCO stands for Orlando Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Tampa Airport (TPA), Orlando Sanford Intl Airport (SFB), Daytona Beach Airport (DAB), Melbourne Airport (MLB).

  • Can I find deals for flights from Chesapeake to Kissimmee that include extra baggage allowance?

    The amount of baggage you can bring on your Chesapeake to Kissimmee flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chesapeake to Kissimmee with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chesapeake to Kissimmee flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chesapeake to Kissimmee that allow pets onboard?

    Many airlines flying from Chesapeake to Kissimmee offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chesapeake to Kissimmee?

    Yes, you can often find last-minute deals on Chesapeake to Kissimmee flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chesapeake to Kissimmee flight deals updated?

    The Chesapeake to Kissimmee flight deals you see on this page were last updated on 11/5.

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

    Currently, December is the cheapest month in which you can book a flight from Chesapeake to Kissimmee (average of $203). Flying from Chesapeake to Kissimmee in November is currently the most expensive (average of $263). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.

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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$126FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$47Average$138FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$59Average$226FlexibilityNo cancel feeOn-time62%
FrontierCheapest$78Average$144FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$81Average$188FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$165Average$338FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$320FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$316FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$189Average$402FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.