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Kissimmee

$43+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Nov 18 — Nov 251
Tue 11/18
Tue 11/25
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Kissimmee are usually found in September or May, booked 31 days in advance, depart on a Thursday 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 October 19, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Priceline)

One-way from

$43
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$237
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. 14% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 19, 2025.

This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/91:11 pmORF - MCO
Nonstop2h 10mFrontier
Thu 11/135:25 amMCO - ORF
1 stop9h 00mFrontier
Deal found 10/19$99
This Priceline deal was found by Cheapflights users on 10/17. 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.
Thu 11/132:00 pmORF - MCO
Nonstop2h 09mMultiple Airlines
Mon 11/1710:27 amMCO - ORF
Nonstop1h 57mMultiple Airlines
Deal found 10/17$100
This Expedia deal was found by Cheapflights users on 10/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2410:28 amORF - MCO
Nonstop2h 12mMultiple Airlines
Fri 11/286:32 pmMCO - ORF
Nonstop1h 59mMultiple Airlines
Deal found 10/16$102
This Priceline deal was found by Cheapflights users on 10/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/29:03 pmORF - MCO
Nonstop2h 07mSpirit Airlines
Thu 11/66:09 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/18$104
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:02 pmORF - MCO
1 stop4h 06mSpirit Airlines
Wed 11/123:40 pmMCO - ORF
Nonstop1h 58mSpirit Airlines
Deal found 10/19$105
This Cheapflightsfares deal was found by Cheapflights users on 10/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/29:03 pmORF - MCO
Nonstop2h 07mSpirit Airlines
Fri 11/710:27 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 10/18$108
This CheapOair deal was found by Cheapflights users on 10/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/141:19 pmORF - MCO
Nonstop2h 11mSpirit Airlines
Fri 11/216:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/17$110
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Sun 11/161:06 pmORF - MCO
Nonstop2h 10mFrontier
Sun 11/2311:14 amMCO - ORF
Nonstop2h 01mFrontier
Deal found 10/17$114
This Cheapflightsfares deal was found by Cheapflights users on 10/17. 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.
Sat 11/86:02 pmORF - MCO
1 stop4h 06mSpirit Airlines
Tue 11/113:40 pmMCO - ORF
Nonstop1h 58mSpirit Airlines
Deal found 10/17$115
This Priceline deal was found by Cheapflights users on 10/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/211:42 amORF - MCO
1 stop5h 21mFrontier
Thu 11/610:20 amMCO - ORF
Nonstop2h 01mFrontier
Deal found 10/18$118

Cheapflights Fare Finder

 
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 October 19, 2025.
Use the filters below to find and compare flights from Chesapeake to Kissimmee that are best for you.

Fly from

Chesapeake

Fly to

Kissimmee

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 1/11

8:32 pm-10:42 pm

Nonstop2h 10m

Orlando

Fri 1/16

5:30 pm-7:37 pm

Nonstop2h 07m

$124

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 11/10

1:19 pm-3:30 pm

Nonstop2h 11m

Orlando

Tue 11/11

10:15 pm-6:58 pm

3 stops20h 43m

$172

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/7

6:03 pm-12:50 am

1 stop6h 47m

Orlando

Sat 12/13

6:15 am-1:26 pm

1 stop7h 11m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 1/14

5:30 am-9:49 am

1 stop4h 19m

Orlando

Tue 1/20

6:15 am-11:47 am

1 stop5h 32m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 1/11

6:05 pm-12:01 am

1 stop5h 56m

Orlando

Fri 1/16

5:15 pm-10:55 pm

1 stop5h 40m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/11

7:00 am-2:37 pm

1 stop7h 37m

Orlando

Mon 12/15

9:00 am-2:09 pm

1 stop5h 09m

$203

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/31

12:15 pm-5:10 pm

1 stop4h 55m

Orlando

Thu 1/1

6:30 am-11:45 am

1 stop5h 15m

$211

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/11

12:38 pm-4:25 pm

1 stop3h 47m

Orlando

Mon 12/15

9:10 am-11:20 am

Nonstop2h 10m

$218

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 12/17

6:00 am-11:06 am

1 stop5h 06m

Orlando

Wed 12/24

2:27 pm-11:41 pm

2 stops9h 14m

$226

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 2/4

8:32 pm-10:42 pm

Nonstop2h 10m

$50

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/17

Showing 1-10 of 19 results
1
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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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Kissimmee

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 October 10, 2025.

The best time to book flights from Chesapeake to Kissimmee is 31 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, September is the cheapest month in which you can book a flight from Chesapeake to Kissimmee (average of $40). Flying from Chesapeake to Kissimmee in December is currently the most expensive (average of $86). 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 October 19, 2025.

When flying from Chesapeake to Kissimmee, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 4% versus a flight at noon.

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 October 19, 2025.

Travelers seeking maximum savings on their Chesapeake to Kissimmee flight should consider departing on Tuesday evenings when fares are most often at their lowest. Wednesday at noon 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 October 19, 2025.

The most flights from C6E to K1S are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, 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 October 19, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and American Airlines from Chesapeake 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.
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,976 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,026 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,104 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,134 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chesapeake to Kissimmee?

    For as low as $124, Spirit Airlines can have you in Kissimmee from Chesapeake in 2h 10m. Chesapeake and Kissimmee are separated by a distance of 655 mi. This flight may include one or multiple stops.

  • 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 Southwest (84%), JetBlue (72%) or Azul (72%) 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 $40. While the most popular route (Norfolk - Orlando) can be booked for $74 on average, our data indicates $178 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, September is the cheapest month in which you can book a flight from Chesapeake to Kissimmee (average of $40). Flying from Chesapeake to Kissimmee in December is currently the most expensive (average of $86). 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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Alternative routes for Chesapeake to Kissimmee

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 October 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$168FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$133FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$134FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$101Average$216FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$106Average$342FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$117Average$269FlexibilityNo cancel feeOn-time62%
DeltaCheapest$134Average$343FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$343FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$436FlexibilityNo cancel feeOn-time69%

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