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$153+ Cheap flights from Kissimmee, FL to Jackson, MS (JAN)

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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — JAN
Feb 23 — Mar 21
Mon 2/23
Mon 3/2
1 adult, Economy
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Cheap flight deals from Kissimmee to Jackson

Cheapest flights from Kissimmee to Jackson
Explore the most affordable flight options available from Kissimmee to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 24, 2026.

This American Airlines deal was found by Cheapflights users on 1/23. 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 3/286:59 pm
MCO
-
JAN
1 stop6h 00m
American Airlines
Sat 4/46:42 pm
JAN
-
MCO
1 stop4h 52m
American Airlines
Deal found 1/23$323
This American Airlines deal was found by Cheapflights users on 1/22. 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.
Tue 3/241:06 pm
MCO
-
JAN
1 stop4h 53m
American Airlines
Sat 3/286:42 pm
JAN
-
MCO
1 stop4h 52m
American Airlines
Deal found 1/22$337
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/126:00 am
MCO
-
JAN
1 stop7h 40m
American Airlines
Mon 2/166:42 pm
JAN
-
MCO
1 stop4h 50m
American Airlines
Deal found 1/21$343
This Southwest deal was found by Cheapflights users on 1/21. 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 2/129:45 am
MCO
-
JAN
1 stop7h 30m
Southwest
Mon 2/1611:50 am
JAN
-
MCO
2 stops6h 55m
Southwest
Deal found 1/21$344
This Southwest deal was found by Cheapflights users on 1/22. 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 5/712:35 pm
MCO
-
JAN
2 stops9h 25m
Southwest
Mon 5/1112:15 pm
JAN
-
MCO
1 stop7h 00m
Southwest
Deal found 1/22$348
This Southwest deal was found by Cheapflights users on 1/23. 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 2/1311:30 am
MCO
-
JAN
1 stop5h 45m
Southwest
Sat 2/2112:25 pm
JAN
-
MCO
2 stops9h 30m
Southwest
Deal found 1/23$349
This Southwest deal was found by Cheapflights users on 1/23. 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.
Sat 3/287:45 am
MCO
-
JAN
1 stop5h 00m
Southwest
Sat 4/45:50 am
JAN
-
MCO
2 stops8h 55m
Southwest
Deal found 1/23$351
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/137:52 pm
MCO
-
JAN
1 stop4h 52m
American Airlines
Mon 2/166:42 pm
JAN
-
MCO
1 stop4h 50m
American Airlines
Deal found 1/21$353

Find flight deals from Kissimmee to Jackson

Keep the following information in mind while searching for Kissimmee to Jackson flight deals. Data was last updated January 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$323
(American Airlines)

One-way from

$153
(United Airlines)

Popular in

March

Cheapest in

November

Average price

$375
Provider with most accurate pricing for Orlando (ORL)-Jackson-Evers Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Jackson-Evers Intl flights.
Search Deals
From Kissimmee to Jackson-Evers Intl
Search Deals
One-way flight from Kissimmee to Jackson-Evers Intl
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 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 Jackson 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 24, 2026.
Use the filters below to find and compare flights from Kissimmee to Jackson that are best for you.

Fly from

Kissimmee

Fly to

Jackson

Route

Depart

Return

Price

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Fri 2/13

11:30 am-4:15 pm

1 stop5h 45m

Jackson-Evers Intl

Sat 2/21

12:25 pm-10:55 pm

2 stops9h 30m

$349

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Sat 3/28

7:45 am-11:45 am

1 stop5h 00m

Jackson-Evers Intl

Sat 4/4

5:50 am-3:45 pm

2 stops8h 55m

$351

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Thu 2/12

11:50 am-9:15 pm

2 stops10h 25m

Jackson-Evers Intl

Mon 2/16

11:50 am-7:45 pm

2 stops6h 55m

$360

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Fri 4/3

5:30 am-8:35 am

1 stop4h 05m

Jackson-Evers Intl

Mon 4/6

7:06 pm-1:04 am

1 stop4h 58m

$369

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Wed 1/28

11:47 am-4:02 pm

1 stop5h 15m

Jackson-Evers Intl

Sat 1/31

2:00 pm-10:12 pm

1 stop7h 12m

$371

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Sat 2/7

9:00 am-4:02 pm

1 stop8h 02m

Jackson-Evers Intl

Sun 2/8

5:15 pm-11:14 pm

1 stop4h 59m

$372

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Sat 2/7

6:05 am-12:20 pm

1 stop7h 15m

Jackson-Evers Intl

Sun 2/8

1:25 pm-7:00 pm

1 stop4h 35m

$372

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Wed 1/28

3:20 pm-8:00 pm

1 stop5h 40m

Jackson-Evers Intl

Sat 1/31

6:00 am-4:40 pm

2 stops9h 40m

$376

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Sat 2/7

7:00 am-12:25 pm

1 stop6h 25m

Jackson-Evers Intl

Sun 2/8

6:15 am-1:12 pm

1 stop5h 57m

$383

OrlandoJackson

MCO - JAN

MCOJAN

Orlando

Tue 4/21

10:35 am-5:30 pm

2 stops7h 55m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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

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

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

Currently, May is the cheapest month in which you can book a flight from Kissimmee to Jackson, Mississippi (average of $198). Flying from Kissimmee to Jackson, Mississippi in January is currently the most expensive (average of $373). 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.

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

Reviews of airlines servicing Jackson

Get insights into the airlines that provide service to Jackson. 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 Jackson. Reviews last updated January 24, 2026.
See what other customers who have flown with Delta from Kissimmee to Jackson have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,110 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,110 reviews
Delta
7.9
Good
8,110 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Entertainment

7.8

Comfort

7.9

Crew

8.5

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Jackson. 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 into for flights to Jackson from Kissimmee?

    Jackson-Evers Intl (JAN) is the airport you will fly into if you book a flight from Kissimmee to Jackson. You should not have trouble finding flights to Jackson-Evers Intl from Kissimmee; the airport handles an average of 0 inbound flights from Kissimmee per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Jackson airport from Kissimmee. It is only a 6.3 mi journey from Jackson-Evers Intl (JAN) to Jackson’s city center.

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

    Departing from Kissimmee to Jackson, Mississippi will take you 5h 45m. The distance from Kissimmee to Jackson, Mississippi is about 587 mi.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $97. Southwest flights start at $124 while deals on Delta start at $174 one-way.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Kissimmee to Jackson, Mississippi (average of $198). Flying from Kissimmee to Jackson, Mississippi in January is currently the most expensive (average of $373). 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

Traveling to a place near Jackson?

Book flights to Jackson if you plan to visit one of these locations
Vicksburg
Clinton
Flowood
Pearl

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Top airline flying from Kissimmee to Jackson

Discover the top airline that operate flights from Kissimmee to Jackson. 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 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$257Average$387FlexibilityNo cancel feeOn-timeN/A

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