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Kissimmee

$49+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 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 21, 2024.

Popular in

August

Cheapest in

February

Round-trip from

$103
(Kiwi.com)

One-way from

$50
(Cheapflightsfares)
High demand for flights, 24% potential price rise
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Best time to find cheap flights, 45% potential price drop
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From Chesapeake to Kissimmee
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One-way flight from Chesapeake to Kissimmee
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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 November 21, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/167:24 pmORF - MCO
Nonstop2h 19mFrontier
Thu 12/199:56 amMCO - ORF
1 stop4h 30mFrontier
Deal found 11/20$110
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/169:19 pmORF - MCO
Nonstop2h 12mMultiple Airlines
Thu 12/199:56 amMCO - ORF
1 stop4h 30mMultiple Airlines
Deal found 11/20$115
This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/59:19 pmORF - MCO
Nonstop2h 12mSpirit Airlines
Fri 12/66:11 pmMCO - ORF
Nonstop2h 13mSpirit Airlines
Deal found 11/20$118
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/79:34 pmORF - MCO
1 stop11h 42mBreeze Airways
Sat 12/146:41 pmMCO - ORF
1 stop13h 57mBreeze Airways
Deal found 11/20$194
This American Airlines deal was found by Cheapflights users on 11/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/143:33 pmORF - MCO
1 stop5h 01mAmerican Airlines
Tue 12/173:13 pmMCO - ORF
1 stop6h 11mAmerican Airlines
Deal found 11/20$236
This United deal was found by Cheapflights users on 11/20. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/148:10 pmORF - MCO
1 stop4h 39mUnited Airlines
Tue 12/1711:00 amMCO - ORF
2 stops12h 30mUnited Airlines
Deal found 11/20$311

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

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Any airport

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 1/5

9:45 am-11:59 am

Nonstop2h 14m

Orlando

Wed 1/15

3:26 pm-5:27 pm

Nonstop2h 01m

$103

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 1/20

3:46 pm-10:15 pm

1 stop6h 29m

Orlando

Sat 1/25

6:07 pm-8:10 pm

Nonstop2h 03m

$105

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 12/9

7:24 pm-9:43 pm

Nonstop2h 19m

Orlando

Mon 12/16

4:32 pm-6:34 pm

Nonstop2h 02m

$109

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/7

9:34 pm-9:16 am

1 stop11h 42m

Orlando

Sat 12/14

6:41 pm-8:38 am

1 stop13h 57m

$194

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 1/8

1:00 pm-7:42 pm

1 stop6h 42m

Orlando

Mon 1/13

6:20 pm-10:21 pm

1 stop4h 01m

$236

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/18

8:08 pm-12:52 am

1 stop4h 44m

Orlando

Wed 12/25

9:00 am-3:18 pm

1 stop6h 18m

$256

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 2/22

7:16 pm-9:35 pm

Nonstop2h 19m

$49

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 12/13

9:19 pm-11:31 pm

Nonstop2h 12m

$50

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/7

9:34 pm-9:16 am

1 stop11h 42m

$77

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 12/7

9:36 pm-10:11 pm

2 stops24h 35m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 14 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 November 15, 2024.

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 $270). 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 21, 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 18, 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.

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 November 21, 2024.

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 (1 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 November 21, 2024.
To help decide which airline to fly from Chesapeake to Kissimmee, see what other customers have to say about Spirit Airlines and American 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.
Breeze Airways
8.2
Very good
123 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.3

Overall

8.2

Crew

8.9

Reviews

1 / 8

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

Breeze Airways
8.2
Very good
123 reviews
Breeze Airways
8.2
Very good
123 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.3

Overall

8.2

Crew

8.9

Reviews

1 / 8

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

Southwest
8.1
Very good
5,005 reviews
Breeze Airways
8.2
Very good
123 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.3

Overall

8.2

Crew

8.9

Reviews

1 / 8

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

Delta
8.0
Very good
8,755 reviews
Breeze Airways
8.2
Very good
123 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.3

Overall

8.2

Crew

8.9

Reviews

1 / 8

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

United Airlines
7.4
Good
9,172 reviews
Breeze Airways
8.2
Very good
123 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.3

Overall

8.2

Crew

8.9

Reviews

1 / 8

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

American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.2
Very good
123 reviews

Boarding

8.4

Entertainment

6.6

Food

6.7

Comfort

8.3

Overall

8.2

Crew

8.9

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.

  • 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 ($50), Frontier ($51), and Breeze Airways ($77).

  • 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 (97%), Azul (89%) or JetBlue (89%) 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 $51. While the most popular route (Norfolk - Orlando) can be booked for $74 on average our data indicates $191 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 $270). 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$128FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$47Average$134FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$59Average$233FlexibilityNo cancel feeOn-time62%
FrontierCheapest$78Average$158FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$81Average$191FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$144Average$428FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$332FlexibilityNo cancel feeOn-time71%
DeltaCheapest$175Average$327FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$207Average$336FlexibilityNo cancel feeOn-time63%
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