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Kissimmee

$50+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Kissimmee are usually found in May or July, booked 56 days in advance, depart on a Thursday or Tuesday 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 July 31, 2025.

Round-trip from

$86
(Mytrip)

One-way from

$50
(FlightHub)

Popular in

November

Cheapest in

May

Average price

$196
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. 13% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/225:20 pmORF - MCO
Nonstop2h 08mSpirit Airlines
Sat 8/302:26 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 7/30$86
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Fri 8/225:20 pmORF - MCO
Nonstop2h 08mMultiple Airlines
Mon 8/256:56 pmMCO - ORF
Nonstop2h 11mMultiple Airlines
Deal found 7/31$92
This Justfly.com deal was found by Cheapflights users on 7/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:39 pmORF - MCO
Nonstop2h 14mFrontier
Sun 8/246:56 pmMCO - ORF
Nonstop2h 11mFrontier
Deal found 7/29$102

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 July 31, 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

Fri 8/22

5:20 pm-7:28 pm

Nonstop2h 08m

Orlando

Sat 8/30

2:26 pm-4:25 pm

Nonstop1h 59m

$86

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 8/22

5:20 pm-7:28 pm

Nonstop2h 08m

Orlando

Mon 8/25

6:56 pm-9:07 pm

Nonstop2h 11m

$92

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 8/14

7:39 pm-9:53 pm

Nonstop2h 14m

Orlando

Sun 8/24

6:56 pm-9:07 pm

Nonstop2h 11m

$102

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 10/12

4:17 pm-6:26 pm

Nonstop2h 09m

$50

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 12/8

5:15 pm-7:30 pm

Nonstop2h 15m

$51

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 12/7

6:00 pm-8:10 pm

Nonstop2h 10m

$52

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 8/29

5:20 pm-7:28 pm

Nonstop2h 08m

$55

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 10/29

7:00 am-2:37 pm

1 stop7h 37m

$89

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 12/4

8:27 pm-12:17 am

1 stop3h 50m

$93

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 25, 2025.

The best time to book flights from Chesapeake to Kissimmee is 53 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 $288). 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 July 31, 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 July 27, 2025.

Travelers seeking maximum savings on their Chesapeake to Kissimmee flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday 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 July 31, 2025.

The most flights from C6E to K1S are scheduled on a Thursday (6 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chesapeake to Kissimmee?

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 July 31, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Breeze Airways 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
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Frontier ($50), Breeze Airways ($51), and Southwest ($52).

  • 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 (81%), Southwest (77%) or JetBlue (69%) 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 $58 on average our data indicates $161 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 $288). 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 2,558,603 searches. Data last updated July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$42Average$161FlexibilityNo cancel feeOn-time65%
FrontierCheapest$50Average$142FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$76Average$135FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$105Average$202FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$125Average$255FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$128Average$346FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$144Average$363FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$167Average$321FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$348FlexibilityNo cancel feeOn-timeN/A

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