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$137+ Cheap flights from Kissimmee

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MCO — AKL
14 May — 21 May1
1 adult
1 adult, Economy, 0 bags

Find flights from Kissimmee within your budget

 
Find flights departing from Kissimmee that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 14 April 2026. In the last 7 days, Cheapflights users made a total of 134,765 searches

Fly to

Route

Departure

Return

Price

Cheapest return flight

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 20/5

07:35-09:45

Nonstop3h 10m

Chicago O'Hare Intl

Wed 20/5

19:35-23:20

Nonstop2h 45m

$289
Fastest return journey

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 23/5

07:00-09:10

Nonstop3h 10m

Chicago O'Hare Intl

Mon 25/5

06:00-09:40

Nonstop2h 40m

$341

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 26/5

07:05-12:50

1 stop6h 45m

Chicago O'Hare Intl

Thu 28/5

14:40-00:05

2 stops8h 25m

$358

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 13/5

08:30-12:50

1 stop5h 20m

Chicago O'Hare Intl

Mon 18/5

14:40-08:25

2 stops16h 45m

$368

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 12/5

21:10-12:50

2 stops16h 40m

Chicago O'Hare Intl

Mon 18/5

10:30-19:00

1 stop7h 30m

$368

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 2/5

08:05-15:30

2 stops8h 25m

Chicago O'Hare Intl

Tue 5/5

14:40-20:30

1 stop4h 50m

$384

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 9/5

08:05-15:30

2 stops8h 25m

Chicago O'Hare Intl

Sat 16/5

13:55-22:20

1 stop7h 25m

$384

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 2/5

07:15-15:30

2 stops9h 15m

Chicago O'Hare Intl

Mon 11/5

14:40-00:05

2 stops8h 25m

$392

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 11/5

21:55-12:50

2 stops15h 55m

Chicago O'Hare Intl

Mon 18/5

14:40-08:25

2 stops16h 45m

$413

OrlandoLas Vegas

MCO - LAS

MCOLAS

Orlando

Tue 1/9

06:40-12:43

1 stop9h 03m

Las Vegas Harry Reid Intl

Fri 11/9

06:00-18:59

1 stop9h 59m

$440

Flights are sorted by cheapest return flights first.

Deals found on 12/4

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Kissimmee

Have a flexible travel schedule? Discover the best time to fly from Kissimmee with our price prediction graph.
Estimated return 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.

Travel insights for flights from Kissimmee

Get recent, data-driven insights about flights from Kissimmee including ideal travel times, pricing trends, and more.

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

Currently, June is the cheapest month in which you can book a flight from Kissimmee (average of $327). Flying from Kissimmee in August will prove the most costly (average of $2,693). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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Related info for your journey

Access useful and relevant information related to your journey from Kissimmee. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 14 April 2026.

  • What is the cheapest airport to fly out of Kissimmee?

    Auckland Intl airport offers the cheapest routes to Amsterdam from $154. Tirana Rinas airport is a great option if you're flying to Rome from $332. Our top recommendation is to be generally flexible with your dates of travel for the best rates.

  • What is the cheapest month to fly from Kissimmee?

    At the present moment the cheapest month to fly from Kissimmee is currently June; with August being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Kissimmee?

    Here are some of the cheapest flight destinations from Kissimmee:
    Fly from Auckland to Christchurch from $154 round trip
    Fly from Auckland to Queenstown from $195 round trip
    Fly from Tirana to Rome from $332 round trip
    Fly from Brindisi to Barcelona from $351 round trip
    Fly from Vienna to Madrid from $401 round trip

  • How does Cheapflights help users find flights from Kissimmee?

    When you search for this flight from Kissimmee, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

  • Why should you use Cheapflights to find cheap flight tickets from Kissimmee?

    It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Kissimmee.

  • Can Cheapflights find flights from Kissimmee with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Kissimmee flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Kissimmee become cheaper?

    Yes, Cheapflights has a feature called Price Alerts, which offers users the ability to be notified when flight prices change. Track prices for your flight from Kissimmee today and book when you’re ready!

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Kissimmee?

When you search for this flight from Kissimmee, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

Why should you use Cheapflights to find cheap flight tickets from Kissimmee?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Kissimmee.

Can Cheapflights find flights from Kissimmee with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Kissimmee flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Kissimmee become cheaper?

Yes, Cheapflights has a feature called Price Alerts, which offers users the ability to be notified when flight prices change. Track prices for your flight from Kissimmee today and book when you’re ready!

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