Kissimmee

$42+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Feb 19 — Feb 261
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Cheapflights Tip: The best prices from Chesapeake to Kissimmee are usually found in September or May, booked 32 days in advance, depart on a Thursday or Sunday and return on a Thursday

Cheap 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 January 20, 2026.

This Frontier deal was found by Cheapflights users on 1/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/319:10 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Sat 2/76:10 pm
MCO
-
ORF
Nonstop2h 05m
Frontier
Deal found 1/18$74
This Kiwi.com deal was found by Cheapflights users on 1/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:45 am
ORF
-
MCO
Nonstop2h 12m
Multiple Airlines
Tue 2/2410:00 am
MCO
-
ORF
Nonstop2h 05m
Multiple Airlines
Deal found 1/18$78
This Super.com deal was found by Cheapflights users on 1/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/54:01 pm
ORF
-
MCO
Nonstop2h 16m
Frontier
Sat 2/149:30 am
MCO
-
ORF
Nonstop2h 05m
Frontier
Deal found 1/18$79
This Frontier deal was found by Cheapflights users on 1/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/54:01 pm
ORF
-
MCO
Nonstop2h 16m
Frontier
Thu 2/124:22 pm
MCO
-
ORF
Nonstop2h 06m
Frontier
Deal found 1/18$80
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/66:45 am
ORF
-
MCO
Nonstop2h 12m
Multiple Airlines
Sat 2/76:10 pm
MCO
-
ORF
Nonstop2h 05m
Multiple Airlines
Deal found 1/20$85
This Super.com deal was found by Cheapflights users on 1/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/56:45 am
ORF
-
MCO
Nonstop2h 12m
Spirit Airlines
Wed 2/113:19 pm
MCO
-
ORF
Nonstop2h 01m
Spirit Airlines
Deal found 1/19$86
This Priceline deal was found by Cheapflights users on 1/18. 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 2/89:37 pm
ORF
-
MCO
Nonstop2h 15m
Multiple Airlines
Sun 2/157:50 pm
MCO
-
ORF
Nonstop2h 00m
Multiple Airlines
Deal found 1/18$87
This Super.com deal was found by Cheapflights users on 1/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/249:10 pm
ORF
-
MCO
Nonstop2h 15m
Frontier
Thu 1/291:00 pm
MCO
-
ORF
Nonstop2h 06m
Frontier
Deal found 1/19$88
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/107:33 pm
ORF
-
MCO
1 stop4h 26m
Multiple Airlines
Fri 2/1312:26 pm
MCO
-
ORF
Nonstop2h 07m
Multiple Airlines
Deal found 1/19$90
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:42 pm
ORF
-
MCO
Nonstop2h 16m
Frontier
Mon 3/26:00 am
MCO
-
ORF
Nonstop2h 04m
Frontier
Deal found 1/20$91
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:31 pm
ORF
-
MCO
1 stop4h 23m
Multiple Airlines
Sat 2/281:46 pm
MCO
-
ORF
Nonstop2h 06m
Multiple Airlines
Deal found 1/20$92
This Kiwi.com deal was found by Cheapflights users on 1/17. 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.
Wed 2/46:15 pm
ORF
-
MCO
1 stop5h 44m
Multiple Airlines
Sat 2/76:10 pm
MCO
-
ORF
Nonstop2h 05m
Multiple Airlines
Deal found 1/17$93

Find flight deals from Chesapeake to Kissimmee

Keep the following information in mind while searching for Chesapeake to Kissimmee flight deals. Data was last updated January 20, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$74
(Frontier)

One-way from

$42
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$193
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
From Chesapeake to Kissimmee
One-way flight from Chesapeake to Kissimmee
Highest demand for flights based on searches. 12% potential increase in price ($28 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in January 2026

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 January 20, 2026.
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

Fri 5/22

5:24 pm-7:40 pm

Nonstop2h 16m

Orlando

Fri 5/29

8:20 pm-10:38 pm

Nonstop2h 18m

$128

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 5/15

5:24 pm-7:40 pm

Nonstop2h 16m

Orlando

Sat 5/23

7:27 pm-9:45 pm

Nonstop2h 18m

$133

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 2/17

6:20 pm-12:06 am

1 stop5h 46m

Orlando

Wed 2/18

6:15 am-11:30 am

1 stop5h 15m

$179

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 5/29

5:24 pm-7:40 pm

Nonstop2h 16m

Orlando

Tue 6/2

12:05 pm-6:16 pm

1 stop6h 11m

$192

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 2/21

5:10 pm-10:50 pm

1 stop5h 40m

Orlando

Tue 2/24

8:50 am-4:45 pm

2 stops7h 55m

$222

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 4/22

4:25 pm-10:40 pm

1 stop6h 15m

Orlando

Mon 4/27

7:35 pm-9:35 pm

Nonstop2h 00m

$227

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 3/2

11:50 am-6:30 pm

1 stop6h 40m

Orlando

Sat 3/7

8:35 am-5:10 pm

2 stops8h 35m

$232

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 2/23

3:30 pm-7:54 pm

1 stop4h 24m

Orlando

Sat 2/28

8:00 am-2:23 pm

1 stop6h 23m

$245

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 3/16

8:20 am-10:30 am

Nonstop2h 10m

$49

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 4/18

6:05 am-8:17 am

Nonstop2h 12m

$50

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/17

Showing 1-10 of 20 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.

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 January 16, 2026.

The best time to book flights from Chesapeake to Kissimmee is 32 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 $43). Flying from Chesapeake to Kissimmee in December is currently the most expensive (average of $84). 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 January 20, 2026.

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 evening, which can drop the price by up to 27% 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 January 17, 2026.

Travelers seeking maximum savings on their Chesapeake to Kissimmee flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday mornings 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 January 20, 2026.

The most flights from C6E to K1S are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 January 20, 2026.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, 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.

Comfort

8.2

Entertainment

6.7

Overall

8.2

Food

6.7

Crew

8.7

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Comfort

8.2

Entertainment

6.7

Overall

8.2

Food

6.7

Crew

8.7

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Comfort

8.2

Entertainment

6.7

Overall

8.2

Food

6.7

Crew

8.7

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Comfort

8.2

Entertainment

6.7

Overall

8.2

Food

6.7

Crew

8.7

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Comfort

8.2

Entertainment

6.7

Overall

8.2

Food

6.7

Crew

8.7

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Comfort

8.2

Entertainment

6.7

Overall

8.2

Food

6.7

Crew

8.7

Boarding

8.3

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 $128, Breeze Airways can have you in Kissimmee from Chesapeake in 2h 16m. Chesapeake and Kissimmee are separated by a distance of 655 mi. This flight may include one or multiple stops.

  • 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 Frontier ($37), Spirit Airlines ($40), and Breeze Airways ($49).

  • 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 Azul (83%), JetBlue (83%) or Southwest (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 $65 on average, our data indicates $236 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 $43). Flying from Chesapeake to Kissimmee in December is currently the most expensive (average of $84). 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

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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.

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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$41Average$143FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$132FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$57Average$150FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$90Average$225FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$98Average$213FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$98Average$338FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$104Average$334FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$138Average$437FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$163Average$353FlexibilityNo cancel feeOn-time71%

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