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Kissimmee

$149+ Cheap flights from Jamaica 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MBJ — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Jamaica to Kissimmee

Cheapest flights from Jamaica to Kissimmee
Explore the most affordable flight options available from Jamaica to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

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.
Fri 2/612:57 pm
MBJ
-
MCO
1 stop11h 02m
Spirit Airlines
Sun 3/16:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Deal found 1/28$265
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/3012:57 pm
MBJ
-
MCO
1 stop11h 02m
Spirit Airlines
Mon 2/236:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Deal found 1/27$266
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 1/306:17 pm
MBJ
-
MCO
Nonstop2h 08m
JetBlue
Mon 2/233:06 pm
MCO
-
MBJ
Nonstop2h 05m
JetBlue
Deal found 1/27$267
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 2/201:00 pm
MBJ
-
MCO
1 stop10h 54m
Spirit Airlines
Mon 3/92:50 pm
MCO
-
MBJ
1 stop21h 12m
Spirit Airlines
Deal found 1/27$269
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:30 pm
MBJ
-
MCO
1 stop8h 45m
Southwest
Sun 2/2210:55 am
MCO
-
MBJ
Nonstop2h 05m
Southwest
Deal found 1/28$272
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.
Tue 2/312:57 pm
MBJ
-
MCO
1 stop11h 02m
Spirit Airlines
Thu 2/196:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Deal found 1/27$274
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.
Wed 2/412:57 pm
MBJ
-
MCO
1 stop11h 02m
Spirit Airlines
Fri 2/206:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Deal found 1/27$275
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/221:00 pm
MBJ
-
MCO
1 stop18h 39m
Spirit Airlines
Sat 3/76:00 am
MCO
-
MBJ
1 stop6h 02m
Spirit Airlines
Deal found 1/29$276
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1112:57 pm
MBJ
-
MCO
1 stop6h 33m
Multiple Airlines
Sat 2/143:06 pm
MCO
-
MBJ
Nonstop2h 05m
Multiple Airlines
Deal found 1/28$280
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/111:07 am
MBJ
-
MCO
1 stop10h 53m
American Airlines
Thu 3/58:43 am
MCO
-
MBJ
1 stop4h 50m
American Airlines
Deal found 1/27$281
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.
Fri 2/201:00 pm
MBJ
-
MCO
1 stop10h 54m
Spirit Airlines
Mon 2/239:54 pm
MCO
-
MBJ
2 stops14h 08m
Spirit Airlines
Deal found 1/28$287
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.
Thu 2/261:17 pm
KIN
-
MCO
1 stop10h 37m
Spirit Airlines
Sun 3/16:00 am
MCO
-
KIN
1 stop6h 15m
Spirit Airlines
Deal found 1/27$318

Find flight deals from Jamaica to Kissimmee

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$266
(Southwest)

One-way from

$149
(Super.com)

Popular in

April

Cheapest in

June

Average price

$350
Provider with most accurate pricing for Montego Bay Sangster Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montego Bay Sangster Intl-Orlando (ORL) flights.
Search Deals
From Jamaica to Kissimmee
Search Deals
One-way flight from Jamaica to Kissimmee
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 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 Jamaica 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 January 29, 2026.
Use the filters below to find and compare flights from Jamaica to Kissimmee that are best for you.

Fly from

Jamaica

Fly to

Kissimmee

Route

Depart

Return

Price

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Mon 2/23

4:15 pm-6:20 pm

Nonstop2h 05m

Orlando

Fri 3/6

7:55 am-3:30 pm

1 stop7h 35m

$266

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Wed 3/4

1:00 pm-7:31 am

2 stops18h 31m

Orlando

Wed 3/11

6:00 am-11:02 am

1 stop6h 02m

$267

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Fri 2/20

1:00 pm-11:54 pm

1 stop10h 54m

Orlando

Mon 2/23

6:54 pm-12:02 pm

1 stop17h 08m

$269

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Thu 2/19

1:00 pm-11:54 pm

1 stop10h 54m

Orlando

Fri 3/6

6:54 pm-12:02 pm

1 stop17h 08m

$269

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Fri 2/20

1:30 pm-10:15 pm

1 stop8h 45m

Orlando

Mon 2/23

1:15 pm-3:15 pm

Nonstop2h 00m

$272

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Fri 2/20

1:30 pm-10:15 pm

1 stop8h 45m

Orlando

Sun 2/22

10:55 am-1:00 pm

Nonstop2h 05m

$272

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Sat 3/28

12:00 pm-11:50 pm

1 stop10h 50m

Orlando

Tue 4/7

10:57 pm-10:58 am

2 stops13h 01m

$274

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Fri 2/20

6:17 pm-8:25 pm

Nonstop2h 08m

Orlando

Mon 2/23

6:00 am-12:02 pm

1 stop6h 02m

$276

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Sun 3/1

6:17 pm-8:25 pm

Nonstop2h 08m

Orlando

Sat 3/7

3:06 pm-5:11 pm

Nonstop2h 05m

$281

Montego BayOrlando

MBJ - MCO

MBJMCO

Montego Bay Sangster Intl

Mon 3/2

6:17 pm-8:25 pm

Nonstop2h 08m

Orlando

Wed 3/4

3:06 pm-5:11 pm

Nonstop2h 05m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 36 results
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Best time to book a flight from Jamaica to Kissimmee

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

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

Currently, November is the cheapest month in which you can book a flight from Jamaica to Kissimmee (average of $180). Flying from Jamaica to Kissimmee in December is currently the most expensive (average of $264). 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 JM to K1S?

Find hourly flight availability from Jamaica 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 January 29, 2026.

When flying from Jamaica to Kissimmee, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 34% versus a flight in the morning.

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 January 29, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and American Airlines from Jamaica 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
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
Delta
7.9
Good
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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 Jamaica to Kissimmee. 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 Jamaica to Kissimmee?

    Airlines like Southwest and Spirit Airlines fly from Jamaica to Kissimmee in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 16h 26m. Jamaica and Kissimmee are separated by a distance of 718 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Jamaica to Kissimmee one-way?

    $130 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on JetBlue and American Airlines, with prices starting from $168 and $191, respectively.

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

    Consider JetBlue (85%), Southwest (59%) or Spirit Airlines (56%) when booking your flight. These represent the most reliable airlines when flying from Jamaica to Kissimmee.

  • What are the cheapest flights from Jamaica to Kissimmee?

    On average you can expect to pay $354 for a flight from Jamaica to Kissimmee. The cheapest flight overall is $130 while the most popular route, (Montego Bay Sangster Intl - Orlando) is currently priced at $231.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Jamaica to Kissimmee (average of $180). Flying from Jamaica to Kissimmee in December is currently the most expensive (average of $264). 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 Jamaica to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Jamaica to Kissimmee

Discover the top 5 airlines that operate flights from Jamaica 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$165Average$311FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$269Average$453FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$284Average$469FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$300Average$434FlexibilityNo cancel feeOn-time63%
DeltaCheapest$462Average$549FlexibilityNo cancel feeOn-timeN/A

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