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Evansville

$45+ Cheap flights from Kissimmee, FL to Evansville (EVV)

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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EVV
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap flight deals from Kissimmee to Evansville

Cheapest flights from Kissimmee to Evansville
Explore the most affordable flight options available from Kissimmee to Evansville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 28, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
MCO
-
EVV
1 stop5h 40m
American Airlines
Sun 2/226:57 pm
EVV
-
MCO
1 stop4h 35m
American Airlines
Deal found 1/26$251
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.
Wed 2/112:45 pm
MCO
-
EVV
1 stop7h 48m
American Airlines
Sun 2/156:57 pm
EVV
-
MCO
1 stop4h 35m
American Airlines
Deal found 1/27$279
This American Airlines deal was found by Cheapflights users on 1/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
MCO
-
EVV
1 stop5h 40m
American Airlines
Thu 2/266:57 pm
EVV
-
MCO
1 stop4h 35m
American Airlines
Deal found 1/26$320
This American Airlines deal was found by Cheapflights users on 1/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:00 am
MCO
-
EVV
1 stop6h 37m
American Airlines
Sat 2/143:50 pm
EVV
-
MCO
1 stop8h 02m
American Airlines
Deal found 1/26$330
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.
Thu 7/239:57 am
MCO
-
EVV
1 stop6h 54m
American Airlines
Sun 8/25:35 am
EVV
-
MCO
1 stop6h 29m
American Airlines
Deal found 1/27$444

Find flight deals from Kissimmee to Evansville

Keep the following information in mind while searching for Kissimmee to Evansville flight deals. Data was last updated January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$45
(Flightnetwork)

Popular in

January

Cheapest in

November

Average price

$412
Provider with most accurate pricing for Orlando (ORL)-Evansville Dress Regional flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Evansville Dress Regional flights.
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From Kissimmee to Evansville Dress Regional
Search Deals
One-way flight from Kissimmee to Evansville Dress Regional
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 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 Evansville 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 28, 2026.
Use the filters below to find and compare flights from Kissimmee to Evansville that are best for you.

Fly from

Kissimmee

Fly to

Evansville

Route

Depart

Return

Price

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Thu 2/19

6:00 am-10:40 am

1 stop5h 40m

Evansville Dress Regional

Sun 2/22

6:57 pm-12:32 am

1 stop4h 35m

$251

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Wed 2/11

2:45 pm-9:33 pm

1 stop7h 48m

Evansville Dress Regional

Sun 2/15

6:57 pm-12:32 am

1 stop4h 35m

$279

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Thu 2/19

6:00 am-10:40 am

1 stop5h 40m

Evansville Dress Regional

Thu 2/26

6:57 pm-12:32 am

1 stop4h 35m

$320

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Tue 2/10

2:05 pm-8:58 pm

2 stops7h 53m

Evansville Dress Regional

Sat 2/14

6:55 pm-12:32 am

1 stop4h 37m

$335

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Thu 7/23

9:57 am-3:51 pm

1 stop6h 54m

Evansville Dress Regional

Sun 8/2

5:35 am-1:04 pm

1 stop6h 29m

$444

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Thu 7/2

6:30 am-11:56 am

1 stop6h 26m

Evansville Dress Regional

Mon 7/6

5:35 am-11:44 am

1 stop5h 09m

$454

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Fri 2/27

5:34 pm-7:06 pm

Nonstop2h 32m

$51

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Mon 5/4

5:34 pm-7:06 pm

Nonstop2h 32m

$51

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Wed 2/18

6:15 am-10:33 am

1 stop5h 18m

$119

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Mon 3/2

6:15 am-10:33 am

1 stop5h 18m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 18 results
1
2

Best time to book a flight from Kissimmee to Evansville

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

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

Currently, May is the cheapest month in which you can book a flight from Kissimmee to Evansville (average of $55). Flying from Kissimmee to Evansville in March is currently the most expensive (average of $102). 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 EVV?

Find hourly flight availability from Kissimmee to Evansville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 28, 2026.

When flying from Kissimmee to Evansville, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Evansville

Get insights into the airlines that provide service to Evansville. 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 Evansville. Reviews last updated January 28, 2026.
Read reviews from past customers who have flown Breeze Airways, Delta, and American Airlines from Kissimmee to Evansville. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

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
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

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
8,124 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

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
11,201 reviews
Breeze Airways
8.2
Very good
263 reviews

Overall

8.2

Food

6.7

Comfort

8.2

Crew

8.7

Boarding

8.3

Entertainment

6.6

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 Kissimmee to Evansville. 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 Evansville from Kissimmee?

    Evansville Dress Regional (EVV) is the airport you will fly into if you book a flight from Kissimmee to Evansville. You should not have trouble finding flights to Dress Regional 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 4 airlines have flights to the Evansville airport from Kissimmee. It is only a 4.4 mi journey from Dress Regional (EVV) to Evansville’s city center.

  • How long is the flight from Kissimmee to Evansville?

    Airlines like American Airlines fly from Kissimmee to Evansville in about 5h 40m. The time it takes to get you to your destination can typically vary by up to . Kissimmee and Evansville are separated by a distance of 754 mi.

  • What are the cheapest flights from Kissimmee to Evansville?

    On average you can expect to pay $177 for a flight from Kissimmee to Evansville. The cheapest flight overall is $69 while the most popular route, (Orlando - Evansville Dress Regional) is currently priced at $313.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Kissimmee to Evansville (average of $55). Flying from Kissimmee to Evansville in March is currently the most expensive (average of $102). 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 Evansville?

Book flights to Evansville if you plan to visit one of these locations
Vincennes
Jasper

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Top 4 airlines flying from Kissimmee to Evansville

Discover the top 4 airlines that operate flights from Kissimmee to Evansville. 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 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$64Average$109FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$92Average$148FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$216Average$418FlexibilityNo cancel feeOn-time71%
DeltaCheapest$230Average$393FlexibilityNo cancel feeOn-timeN/A

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