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Jamaica

$99+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MBJ
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
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 August 21, 2025.

Round-trip from

$270
(SmartFares)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$406
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 ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 21, 2025.

This SmartFares deal was found by Cheapflights users on 8/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/511:00 amMCO - MBJ
Nonstop2h 05mJetBlue
Wed 9/101:13 pmMBJ - MCO
Nonstop2h 09mJetBlue
Deal found 8/21$270
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:31 amMCO - MBJ
1 stop5h 34mSpirit Airlines
Sat 9/2012:10 pmMBJ - MCO
1 stop10h 18mSpirit Airlines
Deal found 8/21$284
This JetBlue deal was found by Cheapflights users on 8/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2912:33 pmMCO - MBJ
Nonstop2h 11mJetBlue
Fri 11/144:31 pmMBJ - MCO
Nonstop2h 09mJetBlue
Deal found 8/20$286
This Priceline deal was found by Cheapflights users on 8/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/811:00 amMCO - MBJ
Nonstop2h 05mJetBlue
Sat 9/131:19 pmMBJ - MCO
Nonstop2h 10mJetBlue
Deal found 8/21$288
This Priceline deal was found by Cheapflights users on 8/20. 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.
Mon 9/811:00 amMCO - MBJ
Nonstop2h 05mJetBlue
Wed 9/101:13 pmMBJ - MCO
Nonstop2h 09mJetBlue
Deal found 8/20$290
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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.
Mon 10/138:37 pmMCO - MBJ
1 stop15h 23mSpirit Airlines
Thu 10/1612:09 pmMBJ - MCO
1 stop9h 42mSpirit Airlines
Deal found 8/21$291
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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.
Mon 9/88:35 pmMCO - MBJ
1 stop15h 30mSpirit Airlines
Sat 9/1312:10 pmMBJ - MCO
1 stop10h 18mSpirit Airlines
Deal found 8/21$292
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/76:31 amMCO - MBJ
1 stop5h 34mSpirit Airlines
Wed 9/1012:10 pmMBJ - MCO
1 stop10h 18mSpirit Airlines
Deal found 8/21$293
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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.
Fri 10/38:35 pmMCO - MBJ
1 stop15h 30mSpirit Airlines
Tue 10/712:09 pmMBJ - MCO
1 stop9h 48mSpirit Airlines
Deal found 8/21$294
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2311:57 amMCO - MBJ
Nonstop2h 04mSpirit Airlines
Sat 8/302:06 pmMBJ - MCO
Nonstop2h 09mSpirit Airlines
Deal found 8/20$295
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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.
Sun 8/316:20 amMCO - MBJ
1 stop5h 54mSpirit Airlines
Sat 9/612:10 pmMBJ - MCO
1 stop10h 18mSpirit Airlines
Deal found 8/21$296
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:31 amMCO - KIN
1 stop5h 31mSpirit Airlines
Wed 9/2412:08 pmKIN - MCO
1 stop10h 20mSpirit Airlines
Deal found 8/20$316

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 August 21, 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 9/13

6:31 am-11:05 am

1 stop5h 34m

Montego Bay Sangster Intl

Sat 9/20

12:10 pm-11:28 pm

1 stop10h 18m

$284

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Tue 9/23

11:00 am-12:05 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Fri 10/3

1:13 pm-4:22 pm

Nonstop2h 09m

$286

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sat 9/13

10:50 am-11:54 am

Nonstop2h 04m

Montego Bay Sangster Intl

Thu 9/18

1:13 pm-4:22 pm

Nonstop2h 09m

$286

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sun 9/21

11:00 am-12:05 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Thu 10/2

1:13 pm-4:22 pm

Nonstop2h 09m

$286

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sat 10/25

10:50 am-11:54 am

Nonstop2h 04m

Montego Bay Sangster Intl

Wed 10/29

3:40 pm-6:47 pm

Nonstop2h 07m

$286

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sun 9/21

11:00 am-12:05 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Fri 10/3

1:13 pm-4:22 pm

Nonstop2h 09m

$286

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Wed 11/12

12:35 pm-2:46 pm

Nonstop2h 11m

Montego Bay Sangster Intl

Wed 11/19

4:31 pm-6:40 pm

Nonstop2h 09m

$286

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Tue 9/23

11:00 am-12:05 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Sat 9/27

1:19 pm-4:29 pm

Nonstop2h 10m

$286

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Wed 9/17

6:31 am-11:02 am

1 stop5h 31m

Kingston Norman Manley

Wed 9/24

12:08 pm-11:28 pm

1 stop10h 20m

$316

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Mon 9/15

8:35 pm-11:02 am

1 stop15h 27m

Kingston Norman Manley

Sat 9/27

12:08 pm-11:28 pm

1 stop10h 20m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 41 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 $560). 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 August 21, 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 Friday afternoons 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 August 21, 2025.

The most flights from K1S to JM0 are scheduled on a Thursday (5 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 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 August 21, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and American Airlines from Kissimmee to Jamaica 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
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,916 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,029 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Kissimmee to Jamaica?

    Spirit Airlines and JetBlue can get you from Kissimmee to Jamaica in just under 2h 05m. Your travel time can differ by up to 3h 29m. Kissimmee and Jamaica are separated by a distance of 718 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 Southwest (83%), JetBlue (80%) or Spirit Airlines (77%) 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 $122. While the most popular route (Orlando - Montego Bay Sangster Intl) can be booked for $256 on average our data indicates $301 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 $560). 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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Tampa to Christiansted flights
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Miami to George Town flights
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Miami to Castries flights
Miami to St. George's flights
Miami to St. John's flights
Fort Lauderdale to Port of Spain flights

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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$358FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$287Average$509FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$322Average$579FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$328Average$554FlexibilityNo cancel feeOn-time71%
DeltaCheapest$370Average$525FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$380Average$452FlexibilityNo cancel feeOn-time62%

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