HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jamaica

$110+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MBJ
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Jamaica with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 27, 2025.

This Priceline deal was found by Cheapflights users on 10/26. 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.
Sun 11/234:45 pmMCO - MBJ
Nonstop2h 04mJetBlue
Wed 11/266:00 pmMBJ - MCO
Nonstop2h 07mJetBlue
Deal found 10/26$306
This Priceline deal was found by Cheapflights users on 10/24. 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 11/1212:35 pmMCO - MBJ
Nonstop2h 11mJetBlue
Tue 11/253:00 pmMBJ - MCO
Nonstop2h 07mJetBlue
Deal found 10/24$308
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 12/76:44 amMCO - MBJ
1 stop5h 26mSpirit Airlines
Thu 12/111:05 pmMBJ - MCO
1 stop4h 24mSpirit Airlines
Deal found 10/26$311
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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 11/25:30 amMCO - MBJ
1 stop5h 32mSpirit Airlines
Tue 12/21:07 pmMBJ - MCO
1 stop5h 21mSpirit Airlines
Deal found 10/26$313
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 11/46:53 amMCO - MBJ
1 stop5h 09mSpirit Airlines
Sat 11/81:07 pmMBJ - MCO
1 stop9h 01mSpirit Airlines
Deal found 10/25$316
This Southwest deal was found by Cheapflights users on 10/26. 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.
Mon 12/812:50 pmMCO - MBJ
Nonstop2h 05mSouthwest
Wed 12/101:00 pmMBJ - MCO
1 stop9h 30mSouthwest
Deal found 10/26$317
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
Sun 11/25:30 amMCO - MBJ
1 stop5h 32mSpirit Airlines
Sat 11/81:07 pmMBJ - MCO
1 stop9h 01mSpirit Airlines
Deal found 10/27$320
This JetBlue deal was found by Cheapflights users on 10/26. 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 12/51:25 pmMCO - MBJ
Nonstop2h 10mJetBlue
Tue 12/94:52 pmMBJ - MCO
Nonstop2h 08mJetBlue
Deal found 10/26$321
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Mon 11/107:50 pmMCO - MBJ
1 stop16h 12mSpirit Airlines
Thu 12/111:05 pmMBJ - MCO
1 stop24h 19mSpirit Airlines
Deal found 10/25$323
This Cheapflightsfares deal was found by Cheapflights users on 10/24. 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.
Thu 10/306:06 amMCO - MBJ
1 stop5h 54mSpirit Airlines
Sat 11/112:09 pmMBJ - MCO
1 stop8h 03mSpirit Airlines
Deal found 10/24$324
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Sat 11/155:00 amMCO - MBJ
2 stops9h 12mAmerican Airlines
Fri 11/2111:17 amMBJ - MCO
1 stop6h 14mAmerican Airlines
Deal found 10/25$326
This CheapOair deal was found by Cheapflights users on 10/24. 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.
Sat 10/256:06 amMCO - MBJ
1 stop5h 54mSpirit Airlines
Wed 10/2912:09 pmMBJ - MCO
1 stop10h 00mSpirit Airlines
Deal found 10/24$327

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 October 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$306
(Priceline)

One-way from

$110
(Cheapflightsfares)

Popular in

December

Cheapest in

November

Average price

$411
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 27, 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

Fri 1/23

3:02 pm-5:07 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Sun 1/25

6:17 pm-8:25 pm

Nonstop2h 08m

$337

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Fri 12/5

1:25 pm-3:35 pm

Nonstop2h 10m

Montego Bay Sangster Intl

Mon 12/8

4:52 pm-7:00 pm

Nonstop2h 08m

$354

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Wed 11/26

4:16 pm-6:20 pm

Nonstop2h 04m

Montego Bay Sangster Intl

Sat 11/29

8:07 pm-10:14 pm

Nonstop2h 07m

$354

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Wed 11/12

12:50 pm-2:55 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Fri 11/21

1:50 pm-4:00 pm

Nonstop2h 10m

$361

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Fri 11/14

12:35 pm-2:46 pm

Nonstop2h 11m

Montego Bay Sangster Intl

Tue 11/18

4:31 pm-6:40 pm

Nonstop2h 09m

$361

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Sun 11/16

10:45 am-12:50 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Sun 12/14

1:50 pm-4:00 pm

Nonstop2h 10m

$369

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Wed 11/19

12:35 pm-2:46 pm

Nonstop2h 11m

Montego Bay Sangster Intl

Sun 11/23

8:07 pm-10:14 pm

Nonstop2h 07m

$369

OrlandoMontego Bay

MCO - MBJ

MCOMBJ

Orlando

Wed 11/12

12:50 pm-2:55 pm

Nonstop2h 05m

Montego Bay Sangster Intl

Wed 11/19

1:00 pm-10:30 pm

1 stop9h 30m

$372

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Mon 12/1

7:50 pm-1:21 pm

1 stop17h 31m

Kingston Norman Manley

Sat 12/6

1:19 pm-7:45 am

1 stop18h 26m

$374

OrlandoKingston

MCO - KIN

MCOKIN

Orlando

Fri 12/5

6:44 am-12:14 pm

1 stop5h 30m

Kingston Norman Manley

Mon 12/8

1:19 pm-7:45 am

1 stop18h 26m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 36 results
1
2
3
4

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 $133). Flying from Kissimmee to Jamaica in February is currently the most expensive (average of $285). 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 October 27, 2025.

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 evening tend to be the most expensive. A flight at noon could potentially save you up to 47% on airfare.

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 Tuesday evenings when fares are most often at their lowest. Sunday evenings 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 October 27, 2025.

The most flights from K1S to JM0 are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 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 October 27, 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
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

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
7.9
Good
7,996 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

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
11,031 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

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
2,906 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

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
8,112 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

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?

    JetBlue, Southwest, and Spirit Airlines can get you from Kissimmee to Jamaica in just under 2h 05m. Your travel time can differ by up to 15h 26m. 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 JetBlue (79%), Southwest (73%) or Spirit Airlines (67%) 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 $132. While the most popular route (Orlando - Montego Bay Sangster Intl) can be booked for $277 on average, our data indicates $331 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 $133). Flying from Kissimmee to Jamaica in February is currently the most expensive (average of $285). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kissimmee to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Orlando to Punta Cana flights
Miami to Santo Domingo flights
Miami to Luis Munoz Marin Intl flights
Fort Lauderdale to Santo Domingo flights
Fort Lauderdale to Punta Cana flights
Miami to Punta Cana flights
Orlando to Ponce flights
Orlando to Santiago de los Caballeros flights
Orlando to Montego Bay flights
Miami to Cap Haitien flights
Orlando to Aguadilla flights
Orlando to Santo Domingo flights
Fort Lauderdale to Montego Bay flights
Miami to Nassau flights
Fort Lauderdale to Kingston flights
Jacksonville to Luis Munoz Marin Intl flights
Miami to Havana flights
Miami to Montego Bay flights
West Palm Beach to Luis Munoz Marin Intl flights
Miami to Oranjestad flights
Miami to Port of Spain flights
Miami to Simpson Bay flights
Fort Lauderdale to Nassau flights
Miami to Willemstad flights
Orlando to Oranjestad flights
Miami to Santiago de los Caballeros flights
Orlando to Nassau flights
Miami to Saint Thomas Island flights
Miami to Castries flights
Miami to Providenciales flights
Fort Lauderdale to Santiago de los Caballeros flights
Tampa to Simpson Bay flights
Miami to Bridgetown flights
Tampa to Santo Domingo flights
Tampa to Punta Cana flights
Fort Lauderdale to Saint Thomas Island flights
Orlando to Saint Thomas Island flights
Fort Lauderdale to Aguadilla flights
Miami to St. John's flights
Miami to Kingston flights
Pensacola to Luis Munoz Marin Intl flights
Tampa to George Town flights
Miami to George Town flights
Miami to The Valley flights
Tampa to Montego Bay flights
Tampa to Oranjestad flights
Fort Lauderdale to Oranjestad 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$124Average$362FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$292Average$504FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$351Average$563FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$355Average$497FlexibilityNo cancel feeOn-time63%
DeltaCheapest$370Average$526FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$378Average$432FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.