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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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Kissimmee are usually found in March or June, booked 31 days in advance, depart on a Tuesday 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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$88
(FlightHub)

One-way from

$43
(FlightHub)

Popular in

October

Cheapest in

March

Average price

$245
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. 8% potential increase in price ($22 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 May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/1511:21 amORF - MCO
Nonstop2h 07mMultiple Airlines
Mon 5/198:29 amMCO - ORF
Nonstop2h 00mMultiple Airlines
Deal found 4/29$88
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 5/1512:13 pmORF - MCO
Nonstop2h 03mSpirit Airlines
Sun 5/188:29 amMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 4/29$89
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/110:43 amORF - MCO
Nonstop2h 01mFrontier
Thu 6/57:40 amMCO - ORF
Nonstop2h 13mFrontier
Deal found 4/30$98
This Delta deal was found by Cheapflights users on 4/29. 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 6/17:40 pmORF - MCO
1 stop4h 44mDelta
Fri 6/67:52 pmMCO - ORF
1 stop4h 26mDelta
Deal found 4/29$177
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/105:50 pmORF - MCO
1 stop5h 56mJetBlue
Tue 9/169:45 amMCO - ORF
1 stop7h 05mJetBlue
Deal found 4/30$209
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/205:00 amORF - MCO
1 stop3h 42mAmerican Airlines
Mon 6/302:06 pmMCO - ORF
1 stop4h 56mAmerican Airlines
Deal found 4/30$247

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 May 1, 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

Thu 5/15

11:21 am-1:28 pm

Nonstop2h 07m

Orlando

Sun 5/18

8:29 am-10:29 am

Nonstop2h 00m

$88

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 5/15

12:13 pm-2:16 pm

Nonstop2h 03m

Orlando

Sun 5/18

8:29 am-10:29 am

Nonstop2h 00m

$89

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 6/1

10:43 am-12:44 pm

Nonstop2h 01m

Orlando

Thu 6/5

7:40 am-9:53 am

Nonstop2h 13m

$98

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 6/1

7:40 pm-12:24 am

1 stop4h 44m

Orlando

Fri 6/6

7:52 pm-12:18 am

1 stop4h 26m

$177

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 6/20

1:37 pm-6:42 pm

1 stop5h 05m

Orlando

Fri 7/4

12:01 pm-6:03 pm

1 stop6h 02m

$199

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 9/10

5:50 pm-11:46 pm

1 stop5h 56m

Orlando

Tue 9/16

9:45 am-4:50 pm

1 stop7h 05m

$209

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 9/10

3:45 pm-5:50 pm

Nonstop2h 05m

Orlando

Tue 9/16

9:05 am-11:00 am

Nonstop1h 55m

$283

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 5/15

12:13 pm-2:16 pm

Nonstop2h 03m

$43

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 5/15

11:21 am-1:28 pm

Nonstop2h 07m

$44

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 6/15

11:35 am-7:18 am

1 stop19h 43m

$87

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 17 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 April 25, 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, 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 $289). 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 May 1, 2025.

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 March 30, 2025.

Travelers seeking maximum savings on their Chesapeake to Kissimmee flight should consider departing on Monday evenings when fares are most often at their lowest. Friday 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 May 1, 2025.

The most flights from C6E to K1S are scheduled on a Thursday (6 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 May 1, 2025.
To help decide which airline to fly from Chesapeake to Kissimmee, see what other customers have to say about Breeze Airways, Southwest and Delta. 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
8.1
Very good
160 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,294 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,934 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,696 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,922 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 ($43), Frontier ($44), and Delta ($89).

  • 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 (95%), Southwest (80%) or JetBlue (76%) 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 $41. While the most popular route (Norfolk - Orlando) can be booked for $45 on average our data indicates $179 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 $289). 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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$150FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$158FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$76Average$135FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$108Average$200FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$122Average$258FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$144Average$378FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$151Average$361FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$166Average$329FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$339FlexibilityNo cancel feeOn-timeN/A

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