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Kissimmee

$44+ Cheap flights from Evansville (EVV) 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — MCO
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheapflights Tip: The best prices from Evansville Dress Regional to Kissimmee are usually found in September or February, booked 69 days in advance, depart on a Monday or Wednesday and return on a Monday

Cheap flight deals from Evansville to Kissimmee

Cheapest flights from Evansville to Kissimmee
Explore the most affordable flight options available from Evansville to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 2026.

This Mytrip deal was found by Cheapflights users on 2/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:46 pm
EVV
-
MCO
Nonstop2h 11m
Breeze Airways
Mon 3/235:34 pm
MCO
-
EVV
Nonstop2h 32m
Breeze Airways
Deal found 2/15$101
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 2/237:46 pm
EVV
-
MCO
Nonstop2h 11m
Breeze Airways
Fri 2/275:34 pm
MCO
-
EVV
Nonstop2h 32m
Breeze Airways
Deal found 2/15$107
This Mytrip deal was found by Cheapflights users on 2/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:46 pm
EVV
-
MCO
Nonstop2h 11m
Breeze Airways
Fri 3/135:34 pm
MCO
-
EVV
Nonstop2h 32m
Breeze Airways
Deal found 2/17$177
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Sat 7/114:29 pm
EVV
-
MCO
Nonstop2h 09m
Breeze Airways
Sat 7/182:24 pm
MCO
-
EVV
Nonstop2h 25m
Breeze Airways
Deal found 2/15$182
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 3/167:46 pm
EVV
-
MCO
Nonstop2h 11m
Breeze Airways
Fri 4/35:34 pm
MCO
-
EVV
Nonstop2h 32m
Breeze Airways
Deal found 2/14$187
This Breeze Airways deal was found by Cheapflights users on 2/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/167:46 pm
EVV
-
MCO
Nonstop2h 11m
Breeze Airways
Fri 2/205:34 pm
MCO
-
EVV
Nonstop2h 32m
Breeze Airways
Deal found 2/15$193
This Breeze Airways deal was found by Cheapflights users on 2/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:46 pm
EVV
-
MCO
Nonstop2h 11m
Breeze Airways
Mon 4/205:34 pm
MCO
-
EVV
Nonstop2h 32m
Breeze Airways
Deal found 2/16$198

Find flight deals from Evansville to Kissimmee

Keep the following information in mind while searching for Evansville to Kissimmee flight deals. Data was last updated February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$101
(Mytrip)

One-way from

$44
(Booking.com)

Popular in

January

Cheapest in

September

Average price

$158
Provider with most accurate pricing for Evansville Dress Regional-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Evansville Dress Regional-Orlando (ORL) flights.
Search Deals
From Evansville Dress Regional to Kissimmee
Search Deals
One-way flight from Evansville Dress Regional to Kissimmee
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Evansville 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 February 18, 2026.
Use the filters below to find and compare flights from Evansville to Kissimmee that are best for you.

Fly from

Evansville

Fly to

Kissimmee

Route

Depart

Return

Price

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 3/16

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Mon 3/23

5:34 pm-7:06 pm

Nonstop2h 32m

$101

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 3/2

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Fri 3/6

5:34 pm-7:06 pm

Nonstop2h 32m

$103

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 4/13

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Mon 4/20

5:34 pm-7:06 pm

Nonstop2h 32m

$198

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Fri 2/20

7:46 pm-10:57 pm

Nonstop2h 11m

Orlando

Fri 2/27

5:34 pm-7:06 pm

Nonstop2h 32m

$218

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 3/16

8:09 am-9:57 am

2 stops24h 48m

Orlando

Mon 3/23

5:34 pm-7:06 pm

Nonstop2h 32m

$228

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Tue 4/28

5:58 pm-12:06 am

1 stop5h 08m

Orlando

Sat 5/2

6:15 am-9:24 am

1 stop4h 09m

$259

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Wed 5/13

4:29 pm-7:38 pm

Nonstop2h 09m

$44

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Mon 3/2

7:46 pm-10:57 pm

Nonstop2h 11m

$49

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Fri 2/27

7:46 pm-10:57 pm

Nonstop2h 11m

$68

EvansvilleOrlando

EVV - MCO

EVVMCO

Evansville Dress Regional

Fri 3/13

7:46 pm-10:57 pm

Nonstop2h 11m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 17 results
1
2

Best time to book a flight from Evansville to Kissimmee

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

How far ahead should I book a flight from Evansville to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Evansville to Kissimmee. Price data was last updated on February 13, 2026.

To ensure you get the cheapest price possible for a flight from Evansville to Kissimmee, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, June is the cheapest month in which you can book a flight from Evansville to Kissimmee (average of $51). Flying from Evansville to Kissimmee in February is currently the most expensive (average of $99). 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 EVV to K1S?

Find hourly flight availability from Evansville 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 February 18, 2026.

A simple way to save on the total cost of your ticket is to fly from Evansville to Kissimmee in the evening. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.

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 February 18, 2026.
Read through reviews of airlines operating flights from Evansville to Kissimmee, such as Breeze Airways, Delta, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
270 reviews

Entertainment

6.7

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
270 reviews
Breeze Airways
8.1
Very good
270 reviews

Entertainment

6.7

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,208 reviews
Breeze Airways
8.1
Very good
270 reviews

Entertainment

6.7

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,304 reviews
Breeze Airways
8.1
Very good
270 reviews

Entertainment

6.7

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Comfort

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Related info for your journey

Find useful and relevant information for your journey from Evansville 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 Evansville to Kissimmee?

    For a flight from Evansville to Kissimmee, you will be flying from Dress Regional. Evansville Dress Regional (EVV) is just 4.4 mi from the center of the city. Dress Regional is the only Evansville airport and it handles 0 outbound flights to Kissimmee per day. 4 airlines have flights to Kissimmee from Evansville Dress Regional on a regular basis.

  • How long is the flight from Evansville to Kissimmee?

    Departing from Evansville to Kissimmee will take you 2h 11m. There are 754 mi between Evansville and Kissimmee. Most flights are nonstop.

  • What are the cheapest flights from Evansville to Kissimmee?

    Looking at all options, your cheapest flight can be booked for $40. While the most popular route (Evansville Dress Regional - Orlando) can be booked for $103 on average, our data indicates $113 when flying from Evansville to Kissimmee.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Evansville to Kissimmee (average of $51). Flying from Evansville to Kissimmee in February is currently the most expensive (average of $99). 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 Evansville to Kissimmee

Discover the top 4 airlines that operate flights from Evansville 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 February 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$76Average$161FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$98Average$138FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$230Average$393FlexibilityNo cancel feeOn-time71%
DeltaCheapest$230Average$392FlexibilityNo cancel feeOn-timeN/A

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