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Jamaica

$98+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MBJ
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Super.com deal was found by Cheapflights users on 1/27. 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.
Thu 2/263:06 pm
MCO
-
MBJ
Nonstop2h 05m
JetBlue
Thu 3/56:17 pm
MBJ
-
MCO
Nonstop2h 08m
JetBlue
Deal found 1/27$295
This Priceline deal was found by Cheapflights users on 1/27. 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.
Fri 2/206:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Wed 2/251:00 pm
MBJ
-
MCO
1 stop10h 54m
Spirit Airlines
Deal found 1/27$296
This Expedia deal was found by Cheapflights users on 1/28. 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.
Fri 2/277:48 pm
MCO
-
MBJ
1 stop15h 36m
Multiple Airlines
Tue 3/36:17 pm
MBJ
-
MCO
Nonstop2h 08m
Multiple Airlines
Deal found 1/28$297
This JetBlue deal was found by Cheapflights users on 1/27. 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.
Fri 2/203:06 pm
MCO
-
MBJ
Nonstop2h 05m
JetBlue
Wed 2/256:17 pm
MBJ
-
MCO
Nonstop2h 08m
JetBlue
Deal found 1/27$298
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/86:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Sat 2/141:00 pm
MBJ
-
MCO
1 stop10h 54m
Spirit Airlines
Deal found 1/29$299
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 2/96:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Fri 2/131:00 pm
MBJ
-
MCO
1 stop10h 54m
Spirit Airlines
Deal found 1/28$301
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:05 am
MCO
-
MBJ
1 stop8h 05m
Southwest
Mon 2/234:15 pm
MBJ
-
MCO
Nonstop2h 05m
Southwest
Deal found 1/27$302
This CheapOair deal was found by Cheapflights users on 1/28. 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.
Tue 3/38:35 pm
MCO
-
MBJ
2 stops15h 27m
Spirit Airlines
Tue 3/1712:00 pm
MBJ
-
MCO
1 stop6h 21m
Spirit Airlines
Deal found 1/28$303
This CheapOair deal was found by Cheapflights users on 1/27. 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 2/96:00 am
MCO
-
MBJ
1 stop6h 02m
Multiple Airlines
Fri 2/136:17 pm
MBJ
-
MCO
Nonstop2h 08m
Multiple Airlines
Deal found 1/27$304
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Fri 3/62:50 pm
MCO
-
MBJ
1 stop21h 12m
Spirit Airlines
Tue 3/1011:57 am
MBJ
-
MCO
1 stop10h 57m
Spirit Airlines
Deal found 1/27$305
This Expedia deal was found by Cheapflights users on 1/27. 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.
Fri 4/109:39 pm
MCO
-
MBJ
1 stop15h 29m
Multiple Airlines
Sat 4/1812:00 pm
MBJ
-
MCO
1 stop10h 58m
Multiple Airlines
Deal found 1/27$306
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/86:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Tue 2/171:00 pm
MBJ
-
MCO
1 stop10h 54m
Spirit Airlines
Deal found 1/29$307

Find flight deals from Kissimmee to Jamaica

Keep the following information in mind while searching for Kissimmee to Jamaica flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$295
(Super.com)

One-way from

$98
(Super.com)

Popular in

December

Cheapest in

November

Average price

$386
Provider with most accurate pricing for Orlando (ORL)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Montego Bay Sangster Intl flights.
Search Deals
From Kissimmee to Jamaica
Search Deals
One-way flight from Kissimmee to Jamaica
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Mon 2/9

3:02 pm-5:07 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Fri 2/13

6:17 pm-8:25 pm

Nonstop2h 08m

$298

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Fri 2/20

3:06 pm-5:11 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Tue 2/24

6:17 pm-8:25 pm

Nonstop2h 08m

$298

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Mon 3/2

3:06 pm-5:11 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Mon 3/9

5:17 pm-8:28 pm

Nonstop2h 11m

$298

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Fri 2/20

3:06 pm-5:11 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Mon 2/23

6:17 pm-8:25 pm

Nonstop2h 08m

$298

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Fri 2/20

3:06 pm-5:11 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Wed 2/25

6:17 pm-8:25 pm

Nonstop2h 08m

$298

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Fri 2/27

10:15 pm-12:10 pm

1 stop13h 55m

Montego Bay Sangster Intl

Fri 3/6

1:55 pm-4:00 pm

Nonstop2h 05m

$302

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Tue 3/31

6:00 am-10:58 am

1 stop5h 58m

Montego Bay Sangster Intl

Sat 4/4

1:13 pm-12:25 am

1 stop10h 12m

$310

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Wed 3/11

6:00 am-11:02 am

1 stop6h 02m

Montego Bay Sangster Intl

Thu 3/19

12:00 pm-7:21 pm

1 stop6h 21m

$311

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Tue 4/7

6:00 am-10:58 am

1 stop5h 58m

Montego Bay Sangster Intl

Sun 4/12

12:00 pm-11:50 pm

1 stop10h 50m

$311

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Mon 3/16

8:55 pm-10:00 am

1 stop14h 05m

Montego Bay Sangster Intl

Wed 3/25

4:49 pm-9:46 am

1 stop15h 57m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 43 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 $125). Flying from Kissimmee to Jamaica in February is currently the most expensive (average of $290). 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 January 29, 2026.

One of the essential ways to save on airfare from Kissimmee to Jamaica is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 29% on airfare.

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 January 29, 2026.
Peruse reviews from past customers who have flown with Southwest, Copa Airlines, 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
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Copa Airlines
7.5
Good
1,560 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,206 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,891 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,394 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    JetBlue and Spirit Airlines can get you from Kissimmee to Jamaica in just under 2h 05m. Your travel time can differ by up to 3h 55m. 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 cheapest airlines to fly from Kissimmee to Jamaica one-way?

    One-way options have recently been found by users for as low as $85 on Spirit Airlines. Other airlines that offer cheap prices include JetBlue from $124 and American Airlines from $132 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 JetBlue (81%), Southwest (50%) or Spirit Airlines (33%) 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 $125. While the most popular route (Orlando - Montego Bay Sangster Intl) can be booked for $278 on average, our data indicates $298 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 $125). Flying from Kissimmee to Jamaica in February is currently the most expensive (average of $290). 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

Browse thousands of different options on Cheapflights for your next trip

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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 7 airlines flying from Kissimmee to Jamaica

Discover the top 7 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$112Average$352FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$277Average$495FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$321Average$594FlexibilityNo cancel feeOn-time71%
DeltaCheapest$330Average$523FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$339Average$498FlexibilityNo cancel feeOn-time63%
FrontierCheapest$380Average$433FlexibilityNo cancel feeOn-time62%
Copa AirlinesCheapest$425Average$518FlexibilityNo cancel feeOn-time70%

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