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Evansville

$59+ 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 12/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — EVV
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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Cheap flight deals from Kissimmee to Evansville

Keep the following information in mind while searching for Kissimmee to Evansville flight deals. Data was last updated November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$108
(Breeze Airways)

One-way from

$59
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$107
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
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One-way flight from Kissimmee to Evansville Dress Regional
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Highest demand for flights based on searches. 4% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/13:25 pmMCO - EVV
Nonstop2h 30mBreeze Airways
Fri 12/55:35 pmEVV - MCO
Nonstop2h 07mBreeze Airways
Deal found 11/24$131
This CheapOair deal was found by Cheapflights users on 11/24. 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.
Fri 12/2610:12 amMCO - EVV
Nonstop2h 30mBreeze Airways
Fri 1/212:22 pmEVV - MCO
Nonstop2h 07mBreeze Airways
Deal found 11/24$132
This Breeze Airways deal was found by Cheapflights users on 11/23. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/53:25 pmMCO - EVV
Nonstop2h 30mBreeze Airways
Mon 12/85:35 pmEVV - MCO
Nonstop2h 07mBreeze Airways
Deal found 11/23$256
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/275:30 amMCO - EVV
1 stop4h 56mDelta
Wed 12/314:26 pmEVV - MCO
1 stop4h 59mDelta
Deal found 11/24$259
This American Airlines deal was found by Cheapflights users on 11/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMCO - EVV
1 stop5h 41mAmerican Airlines
Wed 12/315:10 amEVV - MCO
2 stops7h 17mAmerican Airlines
Deal found 11/24$264
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2210:12 amMCO - EVV
Nonstop2h 30mBreeze Airways
Fri 12/2612:22 pmEVV - MCO
Nonstop2h 07mBreeze Airways
Deal found 11/24$302
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2610:12 amMCO - EVV
Nonstop2h 30mMultiple Airlines
Wed 12/318:29 amEVV - MCO
2 stops24h 36mMultiple Airlines
Deal found 11/24$316
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:30 pmMCO - EVV
1 stop4h 17mDelta
Thu 1/14:26 pmEVV - MCO
1 stop7h 00mDelta
Deal found 11/24$324
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Fri 12/266:00 amMCO - EVV
1 stop5h 41mAmerican Airlines
Wed 12/315:10 amEVV - MCO
2 stops7h 17mAmerican Airlines
Deal found 11/25$329
This Delta deal was found by Cheapflights users on 11/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:15 amMCO - EVV
1 stop4h 11mDelta
Mon 12/85:55 pmEVV - MCO
1 stop5h 55mDelta
Deal found 11/23$370
This American Airlines deal was found by Cheapflights users on 11/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:08 amMCO - EVV
1 stop9h 07mAmerican Airlines
Mon 12/2911:07 amEVV - MCO
1 stop6h 55mAmerican Airlines
Deal found 11/24$381

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 November 25, 2025.
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

Fri 12/26

10:12 am-11:42 am

Nonstop2h 30m

Evansville Dress Regional

Fri 1/2

12:22 pm-3:29 pm

Nonstop2h 07m

$132

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Fri 1/9

5:30 am-10:55 am

1 stop6h 25m

Evansville Dress Regional

Mon 1/12

5:59 pm-11:04 pm

1 stop4h 05m

$231

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Thu 2/5

8:00 am-11:37 am

1 stop4h 37m

Evansville Dress Regional

Sat 2/7

3:48 pm-10:56 pm

1 stop6h 08m

$245

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Fri 12/5

3:25 pm-4:55 pm

Nonstop2h 30m

Evansville Dress Regional

Mon 12/8

5:35 pm-8:42 pm

Nonstop2h 07m

$256

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Sat 12/27

5:30 am-9:26 am

1 stop4h 56m

Evansville Dress Regional

Wed 12/31

4:26 pm-10:25 pm

1 stop4h 59m

$259

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Wed 12/24

3:15 pm-8:47 pm

1 stop6h 32m

Evansville Dress Regional

Wed 12/31

4:26 pm-10:25 pm

1 stop4h 59m

$259

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Sat 12/27

6:15 am-9:26 am

1 stop4h 11m

Evansville Dress Regional

Thu 1/1

4:26 pm-12:26 am

1 stop7h 00m

$259

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Wed 12/24

11:04 am-5:29 pm

2 stops7h 25m

Evansville Dress Regional

Wed 12/31

5:10 am-1:27 pm

2 stops7h 17m

$269

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Mon 12/22

10:12 am-11:42 am

Nonstop2h 30m

Evansville Dress Regional

Fri 12/26

12:22 pm-3:29 pm

Nonstop2h 07m

$302

OrlandoEvansville

MCO - EVV

MCOEVV

Orlando

Fri 1/9

6:15 am-10:55 am

1 stop5h 40m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 21 results
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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 January is currently the most expensive (average of $121). 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 November 25, 2025.

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.

How much does it cost to fly round-trip from Kissimmee to Evansville?

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 November 25, 2025.
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
237 reviews

Boarding

8.4

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
Breeze Airways
8.2
Very good
237 reviews
Breeze Airways
8.2
Very good
237 reviews

Boarding

8.4

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
Delta
7.9
Good
7,998 reviews
Breeze Airways
8.2
Very good
237 reviews

Boarding

8.4

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!
American Airlines
7.2
Good
11,039 reviews
Breeze Airways
8.2
Very good
237 reviews

Boarding

8.4

Entertainment

6.6

Comfort

8.2

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 14
10.0
Excellent

Kim,Nov 2025

PWM - RSW

You guys did a great job getting us here. Thank you!!

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 Breeze Airways, Delta, and American Airlines fly from Kissimmee to Evansville in about 2h 30m. The time it takes to get you to your destination can typically vary by up to 3h 55m. Kissimmee and Evansville are separated by a distance of 754 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Kissimmee to Evansville?

    On average you can expect to pay $136 for a flight from Kissimmee to Evansville. The cheapest flight overall is $98 while the most popular route, (Orlando - Evansville Dress Regional) is currently priced at $108.

  • 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 January is currently the most expensive (average of $121). 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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$68Average$145FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$98Average$123FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$230Average$416FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$263Average$418FlexibilityNo cancel feeOn-time71%

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