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Kissimmee

$153+ Cheap flights from Jackson, MS (JAN) 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MCO
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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Cheapflights Tip: The best prices from Jackson-Evers Intl to Kissimmee are usually found in August or January, booked 40 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Jackson to Kissimmee

Cheapest flights from Jackson to Kissimmee
Explore the most affordable flight options available from Jackson to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 22, 2025.

This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:32 pmJAN - MCO
1 stop4h 51mDelta
Tue 1/65:30 amMCO - JAN
1 stop4h 11mDelta
Deal found 12/20$373
This Southwest deal was found by Cheapflights users on 12/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:10 pmJAN - MCO
1 stop3h 50mSouthwest
Fri 12/266:30 pmMCO - JAN
1 stop4h 35mSouthwest
Deal found 12/20$374
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:25 amJAN - MCO
1 stop4h 40mSouthwest
Sat 12/275:50 pmMCO - JAN
1 stop5h 40mSouthwest
Deal found 12/21$426
This Southwest deal was found by Cheapflights users on 12/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:20 amJAN - MCO
1 stop7h 10mSouthwest
Mon 12/296:45 amMCO - JAN
1 stop5h 20mSouthwest
Deal found 12/21$427
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/282:03 pmJAN - MCO
1 stop5h 09mUnited Airlines
Tue 1/63:30 pmMCO - JAN
1 stop7h 27mUnited Airlines
Deal found 12/20$433
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/282:03 pmJAN - MCO
1 stop5h 09mUnited Airlines
Sun 1/119:00 amMCO - JAN
1 stop5h 22mUnited Airlines
Deal found 12/21$445
This Delta deal was found by Cheapflights users on 12/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amJAN - MCO
1 stop6h 10mDelta
Tue 1/68:00 amMCO - JAN
1 stop4h 17mDelta
Deal found 12/20$456

Find flight deals from Jackson to Kissimmee

Keep the following information in mind while searching for Jackson to Kissimmee flight deals. Data was last updated December 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$305
(Southwest)

One-way from

$153
(American Airlines)

Popular in

October

Cheapest in

August

Average price

$456
Provider with most accurate pricing for Jackson-Evers Intl-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Jackson-Evers Intl-Orlando (ORL) flights.
Search Deals
From Jackson-Evers Intl to Kissimmee
Search Deals
One-way flight from Jackson-Evers Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Jackson 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 December 22, 2025.
Use the filters below to find and compare flights from Jackson to Kissimmee that are best for you.

Fly from

Jackson

Fly to

Kissimmee

Route

Depart

Return

Price

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Wed 3/4

3:20 pm-10:15 pm

1 stop5h 55m

Orlando

Tue 3/10

7:10 am-11:30 am

1 stop5h 20m

$305

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Sat 1/17

12:50 pm-9:06 pm

1 stop7h 16m

Orlando

Tue 1/20

6:00 am-12:25 pm

1 stop7h 25m

$316

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Mon 1/19

5:15 pm-11:14 pm

1 stop4h 59m

Orlando

Mon 1/26

9:00 am-1:22 pm

1 stop5h 22m

$327

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Sat 2/14

4:15 pm-10:55 pm

1 stop5h 40m

Orlando

Sat 2/21

11:10 am-3:40 pm

1 stop5h 30m

$327

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Tue 3/3

1:25 pm-8:00 pm

2 stops5h 35m

Orlando

Sat 3/7

1:05 pm-9:50 pm

2 stops9h 45m

$338

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Sun 1/11

2:00 pm-10:12 pm

1 stop7h 12m

Orlando

Wed 1/14

9:00 am-1:22 pm

1 stop5h 22m

$340

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Sat 1/3

6:30 pm-12:10 am

1 stop4h 40m

Orlando

Sat 1/10

9:20 am-5:10 pm

2 stops8h 50m

$344

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Wed 1/14

6:40 am-4:05 pm

2 stops8h 25m

Orlando

Fri 1/16

10:20 am-3:40 pm

1 stop6h 20m

$345

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Sun 1/11

11:50 am-7:00 pm

2 stops6h 10m

Orlando

Wed 1/14

3:20 pm-8:00 pm

1 stop5h 40m

$345

JacksonOrlando

JAN - MCO

JANMCO

Jackson-Evers Intl

Sun 2/1

2:00 pm-7:44 pm

1 stop4h 44m

Orlando

Sat 2/7

7:00 am-1:22 pm

1 stop7h 22m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 21 results
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Best time to book a flight from Jackson to Kissimmee

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

How far ahead should I book a flight from Jackson, Mississippi to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Jackson to Kissimmee. Price data was last updated on December 19, 2025.

Booking 40 days in advance of your planned departure date is, on average, the best time to get cheap flights from Jackson, Mississippi to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Jackson, Mississippi to Kissimmee?

Currently, September is the cheapest month in which you can book a flight from Jackson, Mississippi to Kissimmee (average of $224). Flying from Jackson, Mississippi to Kissimmee in November is currently the most expensive (average of $348). 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 JAN to K1S?

Find hourly flight availability from Jackson 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 December 22, 2025.

It’s typically best to fly out from Jackson, Mississippi to Kissimmee in the evening. Doing so could potentially save you 14% on the flight price compared to flying in the morning, which is usually more expensive.

How much does it cost to fly round-trip from Jackson, Mississippi to Kissimmee?

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 December 22, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Jackson to Kissimmee by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
8,014 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
United Airlines
7.4
Good
9,102 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
11,051 reviews
Southwest
8.0
Very good
4,254 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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 Jackson to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Jackson to Kissimmee?

    Jackson-Evers Intl (JAN) is the airport you will fly out of if you book a flight from Jackson to Kissimmee. You should not have trouble finding flights to Kissimmee from Jackson-Evers Intl; the airport handles an average of 0 outbound flights to Kissimmee per day. You should also have plenty of airline options to choose from since 4 airlines have flights from the Jackson airport to Kissimmee. It is only a 6.3 mi journey to Jackson-Evers Intl (JAN) from Jackson’s city center.

  • How long is the flight from Jackson, Mississippi to Kissimmee?

    Airlines like Southwest, American Airlines, and United Airlines fly from Jackson, Mississippi to Kissimmee in about 4h 59m. The time it takes to get you to your destination can typically vary by up to 2h 17m. The distance from Jackson, Mississippi to Kissimmee is about 587 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Jackson, Mississippi to Kissimmee one-way?

    The cheapest airlines for a one-way flight from Jackson, Mississippi to Kissimmee are Delta ($124), Southwest ($137), and American Airlines ($191).

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jackson 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 Jackson, Mississippi to Kissimmee?

    Currently, September is the cheapest month in which you can book a flight from Jackson, Mississippi to Kissimmee (average of $224). Flying from Jackson, Mississippi to Kissimmee in November is currently the most expensive (average of $348). 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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Top 4 airlines flying from Jackson to Kissimmee

Discover the top 4 airlines that operate flights from Jackson 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 December 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$232Average$368FlexibilityNo cancel feeOn-time69%
DeltaCheapest$253Average$388FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$254Average$381FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$258Average$414FlexibilityNo cancel feeOn-time71%

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