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$100+ Cheap flights from Kissimmee, FL to Jamaica

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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MBJ
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
1 adult, Economy
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Cheap flight deals from Kissimmee to Jamaica

Keep the following information in mind while searching for Kissimmee to Jamaica flight deals. Data was last updated June 23, 2025.

Round-trip from

$262
(Cheapflightsfares)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$449
From Kissimmee to Jamaica
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One-way flight from Kissimmee to Jamaica
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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Kissimmee to Jamaica

Cheapest flights from Kissimmee to Jamaica
Explore the most affordable flight options available from Kissimmee to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 23, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 9/69:59 amMCO - MBJ
Nonstop2h 07mSpirit Airlines
Sat 9/1312:11 pmMBJ - MCO
Nonstop2h 09mSpirit Airlines
Deal found 6/21$262
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Sun 7/276:05 amMCO - MBJ
Nonstop2h 03mJetBlue
Thu 7/318:10 amMBJ - MCO
Nonstop2h 03mJetBlue
Deal found 6/23$306
This Cheapflightsfares deal was found by Cheapflights users on 6/22. 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.
Tue 8/129:38 pmMCO - KIN
1 stop14h 49mSpirit Airlines
Wed 8/2012:32 pmKIN - MCO
1 stop8h 49mSpirit Airlines
Deal found 6/22$323
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Sun 9/217:00 amMCO - MBJ
1 stop9h 09mAmerican Airlines
Wed 10/13:36 pmMBJ - MCO
2 stops19h 13mAmerican Airlines
Deal found 6/21$325
This CheapOair deal was found by Cheapflights users on 6/21. 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.
Mon 8/46:50 amMCO - MBJ
1 stop5h 15mMultiple Airlines
Tue 8/123:45 pmMBJ - MCO
1 stop15h 43mMultiple Airlines
Deal found 6/21$351
This Frontier deal was found by Cheapflights users on 6/22. 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.
Tue 8/56:45 amMCO - MBJ
1 stop8h 52mFrontier
Fri 8/89:05 amMBJ - MCO
1 stop7h 17mFrontier
Deal found 6/22$381
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 8/126:50 amMCO - KIN
1 stop14h 45mMultiple Airlines
Fri 8/2212:32 pmKIN - MCO
1 stop8h 49mMultiple Airlines
Deal found 6/23$400
This American Airlines deal was found by Cheapflights users on 6/23. 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.
Thu 11/206:00 amMCO - KIN
1 stop7h 55mAmerican Airlines
Tue 11/254:00 pmKIN - MCO
1 stop7h 46mAmerican Airlines
Deal found 6/23$519

Cheapflights Fare Finder

Customize your flight search to find flights from Kissimmee to Jamaica 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 June 23, 2025.
Use the filters below to find and compare flights from Kissimmee to Jamaica that are best for you.

Fly from

Kissimmee

Fly to

Jamaica

Route

Depart

Return

Price

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sat 9/6

9:59 am-11:06 am

Nonstop2h 07m

Montego Bay Sangster Intl

Sat 9/13

12:11 pm-3:20 pm

Nonstop2h 09m

$262

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sun 7/27

4:15 pm-5:25 pm

Nonstop2h 10m

Montego Bay Sangster Intl

Wed 8/6

1:10 pm-4:23 pm

Nonstop2h 13m

$306

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Tue 8/12

9:38 pm-11:27 am

1 stop14h 49m

Kingston Norman Manley

Wed 8/20

12:32 pm-10:21 pm

1 stop8h 49m

$323

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sun 9/21

7:00 am-3:09 pm

1 stop9h 09m

Montego Bay Sangster Intl

Wed 10/1

3:36 pm-11:49 am

2 stops19h 13m

$325

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Mon 8/4

6:50 am-11:05 am

1 stop5h 15m

Montego Bay Sangster Intl

Tue 8/12

3:45 pm-8:28 am

1 stop15h 43m

$351

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Tue 8/5

9:40 pm-7:55 am

1 stop11h 15m

Montego Bay Sangster Intl

Sat 8/9

12:12 pm-11:14 pm

1 stop10h 02m

$381

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Thu 8/7

6:50 am-11:00 am

1 stop5h 10m

Kingston Norman Manley

Fri 8/22

6:25 pm-7:44 pm

3 stops24h 19m

$408

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Mon 7/21

6:36 pm-1:29 pm

2 stops19h 53m

Kingston Norman Manley

Mon 7/28

6:00 am-12:06 am

2 stops17h 06m

$553

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Wed 9/3

7:20 pm-7:51 am

1 stop13h 31m

Kingston Norman Manley

Fri 9/12

2:10 am-5:45 pm

1 stop14h 35m

$616

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sat 7/19

8:10 pm-9:53 am

1 stop14h 43m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 22 results
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Best time to book a flight from Kissimmee to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Kissimmee 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 Kissimmee to Jamaica

What is the cheapest month to book a flight from Kissimmee to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Kissimmee to Jamaica (average of $403). Flying from Kissimmee to Jamaica in July is currently the most expensive (average of $569). 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 K1S to JM?

Find hourly flight availability from Kissimmee to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 23, 2025.

When flying from Kissimmee to Jamaica, 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 Kissimmee to Jamaica?

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Jamaica. Price data was last updated on December 16, 2024.

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

Weekly flight availability from Kissimmee to Jamaica

Explore weekly flight availability from Kissimmee to Jamaica. 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 June 23, 2025.

The most flights from K1S to JM0 are scheduled on a Saturday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated June 23, 2025.
Read reviews from past customers who have flown Caribbean Airlines, Southwest and Copa Airlines from Kissimmee to Jamaica. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.2
Very good
160 reviews

Boarding

8.2

Overall

8.2

Food

6.8

Comfort

7.9

Crew

8.5

Entertainment

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
Caribbean Airlines
8.2
Very good
160 reviews
Caribbean Airlines
8.2
Very good
160 reviews

Boarding

8.2

Overall

8.2

Food

6.8

Comfort

7.9

Crew

8.5

Entertainment

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
Southwest
8.0
Very good
4,278 reviews
Caribbean Airlines
8.2
Very good
160 reviews

Boarding

8.2

Overall

8.2

Food

6.8

Comfort

7.9

Crew

8.5

Entertainment

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
Copa Airlines
7.5
Good
1,460 reviews
Caribbean Airlines
8.2
Very good
160 reviews

Boarding

8.2

Overall

8.2

Food

6.8

Comfort

7.9

Crew

8.5

Entertainment

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
United Airlines
7.4
Good
8,831 reviews
Caribbean Airlines
8.2
Very good
160 reviews

Boarding

8.2

Overall

8.2

Food

6.8

Comfort

7.9

Crew

8.5

Entertainment

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.
JetBlue
7.3
Good
2,922 reviews
Caribbean Airlines
8.2
Very good
160 reviews

Boarding

8.2

Overall

8.2

Food

6.8

Comfort

7.9

Crew

8.5

Entertainment

6.8

Reviews

1 / 9
6.0
Good

Anonymous,Mar 2025

JFK - GEO

Air hostesses were friendly. There should be more options for tea.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Jamaica. 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 Kissimmee to Jamaica one-way?

    One-way options have recently been found by users for as low as $100 on Spirit Airlines. Other airlines that offer cheap prices include JetBlue from $132 and American Airlines from $137 one-way.

  • What are the most reliable airlines from Kissimmee to Jamaica?

    No one likes to see their flight delayed. When booking a flight from Kissimmee to Jamaica consider choosing Spirit Airlines (100%), JetBlue (96%) or Southwest (81%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Kissimmee to Jamaica?

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Orlando - Montego Bay Sangster Intl) can be booked for $262 on average our data indicates $342 when flying from Kissimmee to Jamaica.

  • Can I find deals for flights from Kissimmee to Jamaica that include hotel bookings?

    Yes. In addition to deals on Kissimmee to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kissimmee to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kissimmee to Jamaica.

  • Can I find deals for business class flights from Kissimmee to Jamaica?

    Yes. Cheapflights offers flight deals from Kissimmee to Jamaica 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 Kissimmee to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Kissimmee to Jamaica (average of $403). Flying from Kissimmee to Jamaica in July is currently the most expensive (average of $569). 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 Kissimmee to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Kissimmee to Jamaica

Discover the top 6 airlines that operate flights from Kissimmee to Jamaica. 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 June 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$97Average$362FlexibilityNo cancel feeOn-time65%
FrontierCheapest$302Average$452FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$302Average$510FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$321Average$491FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$350Average$565FlexibilityNo cancel feeOn-time71%
DeltaCheapest$370Average$534FlexibilityNo cancel feeOn-timeN/A

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