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Kissimmee

$40+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
ene. 2 — ene. 91
vie. 1/2
vie. 1/9
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 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 diciembre 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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.
mar. 12/307:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
mar. 1/64:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/2$92
This Super.com deal was found by Cheapflights users on 12/2. 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.
lun. 12/158:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
sáb. 12/204:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/2$93
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
lun. 12/156:15 amORF - MCO
Nonstop2h 15mBreeze Airways
vie. 12/193:00 pmMCO - ORF
Nonstop2h 10mBreeze Airways
Deal found 12/2$98
This Super.com deal was found by Cheapflights users on 12/1. 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.
sáb. 12/207:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
mar. 12/234:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/1$100
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
lun. 12/88:00 amORF - MCO
Nonstop2h 15mBreeze Airways
vie. 12/1210:55 amMCO - ORF
Nonstop2h 10mBreeze Airways
Deal found 12/2$102
This Cheapflightsfares deal was found by Cheapflights users on 12/1. 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.
lun. 12/158:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
mar. 12/304:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/1$105
This Super.com deal was found by Cheapflights users on 12/1. 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.
jue. 12/257:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
mar. 1/64:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/1$111
This Mytrip deal was found by Cheapflights users on 12/1. 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.
lun. 12/158:11 pmORF - MCO
1 stop11h 34mSpirit Airlines
jue. 12/184:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/1$115
This Cheapflightsfares deal was found by Cheapflights users on 12/2. 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.
dom. 12/148:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
lun. 12/224:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/2$119
This Expedia deal was found by Cheapflights users on 12/1. 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.
vie. 12/128:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
lun. 12/155:46 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 12/1$120
This Expedia deal was found by Cheapflights users on 11/30. 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.
dom. 12/148:38 amORF - MCO
Nonstop2h 12mMultiple Airlines
mié. 12/174:51 pmMCO - ORF
Nonstop2h 10mMultiple Airlines
Deal found 11/30$121
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
lun. 12/88:00 amORF - MCO
Nonstop2h 15mMultiple Airlines
lun. 12/155:46 amMCO - ORF
Nonstop1h 57mMultiple Airlines
Deal found 12/2$123

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 diciembre 3, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$88
(Frontier)

One-way from

$40
(Super.com)

Popular in

November

Cheapest in

September

Average price

$251
Provider with most accurate pricing for Norfolk-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Orlando (ORL) flights.
Search Deals
From Chesapeake to Kissimmee
Search Deals
One-way flight from Chesapeake to Kissimmee
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 diciembre 3, 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

sáb. 2/14

6:45 am-8:57 am

Nonstop2h 12m

Orlando

dom. 2/22

7:50 pm-9:50 pm

Nonstop2h 00m

$109

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mar. 12/23

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

lun. 12/29

6:45 am-2:06 pm

1 stop7h 21m

$137

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 12/8

8:38 am-10:50 am

Nonstop2h 12m

Orlando

jue. 12/11

10:02 am-4:47 pm

1 stop6h 45m

$139

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 1/12

12:40 pm-5:40 pm

1 stop5h 00m

Orlando

mar. 1/13

11:50 am-8:30 pm

1 stop8h 40m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

jue. 2/5

6:11 pm-12:59 am

1 stop6h 48m

Orlando

mié. 2/11

11:10 am-5:19 pm

1 stop6h 09m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

vie. 1/30

7:33 pm-11:59 pm

1 stop4h 26m

Orlando

dom. 2/1

9:46 pm-6:38 pm

2 stops20h 52m

$181

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 1/19

7:33 pm-9:59 am

3 stops38h 26m

Orlando

sáb. 1/24

7:50 pm-9:50 pm

Nonstop2h 00m

$188

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mié. 1/14

4:10 pm-6:25 pm

Nonstop2h 15m

Orlando

mié. 1/21

7:00 am-12:10 pm

1 stop5h 10m

$192

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mar. 1/27

6:30 am-1:04 pm

1 stop6h 34m

Orlando

sáb. 1/31

5:45 pm-11:27 pm

1 stop5h 42m

$201

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

sáb. 12/27

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

lun. 12/29

4:40 pm-6:45 pm

Nonstop2h 05m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 20 results
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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 November 28, 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 $42). Flying from Chesapeake to Kissimmee in June is currently the most expensive (average of $83). 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 diciembre 3, 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 3% 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 November 29, 2025.

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

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 diciembre 3, 2025.
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.
Breeze Airways
8.2
Very good
241 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Comfort

8.2

Overall

8.2

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Breeze Airways
8.2
Very good
241 reviews
Breeze Airways
8.2
Very good
241 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Comfort

8.2

Overall

8.2

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Southwest
8.0
Very good
4,254 reviews
Breeze Airways
8.2
Very good
241 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Comfort

8.2

Overall

8.2

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
American Airlines
7.2
Good
11,046 reviews
Breeze Airways
8.2
Very good
241 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Comfort

8.2

Overall

8.2

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Spirit Airlines
6.3
Okay
8,161 reviews
Breeze Airways
8.2
Very good
241 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Comfort

8.2

Overall

8.2

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Frontier
5.8
Fair
3,092 reviews
Breeze Airways
8.2
Very good
241 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Comfort

8.2

Overall

8.2

Entertainment

6.6

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

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 $109, Spirit Airlines can have you in Kissimmee from Chesapeake in 2h 12m. 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 ($39), and Breeze Airways ($54).

  • 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 JetBlue (86%), Southwest (86%) or Azul (79%) 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 $38. While the most popular route (Norfolk - Orlando) can be booked for $51 on average, our data indicates $168 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 $42). Flying from Chesapeake to Kissimmee in June is currently the most expensive (average of $83). 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 diciembre 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$160FlexibilityNo cancel feeOn-time65%
FrontierCheapest$54Average$152FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$75Average$129FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$100Average$339FlexibilityNo cancel feeOn-time63%
Breeze AirwaysCheapest$102Average$219FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$117Average$240FlexibilityNo cancel feeOn-time62%
DeltaCheapest$129Average$351FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$343FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$428FlexibilityNo cancel feeOn-time69%

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