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Kissimmee

$253+ Cheap flights from Helena (HLN) 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
HLN — MCO
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Helena to Kissimmee

Cheapest flights from Helena to Kissimmee
Explore the most affordable flight options available from Helena to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This United Airlines deal was found by Cheapflights users on 2/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:30 pm
HLN
-
MCO
1 stop6h 55m
United Airlines
Tue 3/179:00 am
MCO
-
HLN
2 stops14h 25m
United Airlines
Deal found 2/12$334
This United Airlines deal was found by Cheapflights users on 2/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:25 pm
HLN
-
MCO
1 stop7h 05m
United Airlines
Tue 3/39:00 am
MCO
-
HLN
2 stops14h 16m
United Airlines
Deal found 2/12$394
This United Airlines deal was found by Cheapflights users on 2/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/122:30 pm
HLN
-
MCO
1 stop6h 55m
United Airlines
Tue 3/179:26 am
MCO
-
HLN
2 stops13h 59m
United Airlines
Deal found 2/12$414
This United Airlines deal was found by Cheapflights users on 2/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 am
HLN
-
MCO
1 stop6h 54m
United Airlines
Fri 8/288:20 am
MCO
-
HLN
1 stop7h 07m
United Airlines
Deal found 2/10$428
This United Airlines deal was found by Cheapflights users on 2/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:30 pm
HLN
-
MCO
1 stop6h 38m
United Airlines
Sat 9/510:30 am
MCO
-
HLN
1 stop7h 35m
United Airlines
Deal found 2/9$429
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:22 pm
HLN
-
MCO
1 stop27h 37m
Alaska Airlines
Wed 4/297:15 am
MCO
-
HLN
1 stop12h 30m
Alaska Airlines
Deal found 2/11$458
This United Airlines deal was found by Cheapflights users on 2/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/252:25 pm
HLN
-
MCO
1 stop7h 05m
United Airlines
Thu 3/56:00 am
MCO
-
HLN
1 stop9h 38m
United Airlines
Deal found 2/11$459
This Delta deal was found by Cheapflights users on 2/12. 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.
Thu 3/51:10 pm
HLN
-
MCO
1 stop8h 40m
Delta
Tue 4/77:10 am
MCO
-
HLN
1 stop7h 11m
Delta
Deal found 2/12$464

Find flight deals from Helena to Kissimmee

Keep the following information in mind while searching for Helena to Kissimmee flight deals. Data was last updated February 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(United Airlines)

One-way from

$253
(Alaska Airlines)

Popular in

November

Cheapest in

September

Average price

$856
Provider with most accurate pricing for Helena-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Helena-Orlando (ORL) flights.
Search Deals
From Helena to Kissimmee
Search Deals
One-way flight from Helena to Kissimmee
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($224 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($57 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 Helena 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 13, 2026.
Use the filters below to find and compare flights from Helena to Kissimmee that are best for you.

Fly from

Helena

Fly to

Kissimmee

Route

Depart

Return

Price

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Wed 3/11

2:30 pm-11:25 pm

1 stop6h 55m

Orlando

Tue 3/17

9:00 am-9:25 pm

2 stops14h 25m

$334

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Fri 2/27

2:25 pm-11:30 pm

1 stop7h 05m

Orlando

Tue 3/3

9:00 am-9:16 pm

2 stops14h 16m

$394

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Thu 3/12

2:30 pm-11:25 pm

1 stop6h 55m

Orlando

Thu 3/19

6:00 am-1:38 pm

1 stop9h 38m

$408

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Thu 3/12

2:30 pm-11:25 pm

1 stop6h 55m

Orlando

Tue 3/17

9:26 am-9:25 pm

2 stops13h 59m

$414

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Wed 4/22

6:22 pm-11:59 pm

1 stop27h 37m

Orlando

Wed 4/29

7:15 am-5:45 pm

1 stop12h 30m

$458

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Wed 4/22

6:15 am-8:09 pm

2 stops11h 54m

Orlando

Wed 4/29

12:06 pm-9:33 pm

2 stops11h 27m

$458

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Thu 3/5

1:10 pm-11:50 pm

1 stop8h 40m

Orlando

Tue 4/7

7:10 am-12:21 pm

1 stop7h 11m

$464

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Sat 5/2

6:22 pm-5:55 am

2 stops33h 33m

Orlando

Fri 5/8

7:27 pm-5:45 pm

2 stops24h 18m

$473

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Thu 3/19

2:30 pm-11:25 pm

1 stop6h 55m

Orlando

Mon 3/23

6:00 am-1:38 pm

1 stop9h 38m

$476

HelenaOrlando

HLN - MCO

HLNMCO

Helena

Wed 3/4

4:36 pm-5:40 am

2 stops35h 04m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 12 results
1
2

Best time to book a flight from Helena to Kissimmee

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

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

Currently, July is the cheapest month in which you can book a flight from Helena to Kissimmee (average of $128). Flying from Helena to Kissimmee in October is currently the most expensive (average of $305). 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.

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 13, 2026.
Peruse reviews from past customers who have flown with Delta and United Airlines from Helena to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,194 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,194 reviews
Delta
7.9
Good
8,194 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
9,283 reviews
Delta
7.9
Good
8,194 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

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

    Helena (HLN), located 2.7 mi from the city center, is the airport you fly out of when you book flights from Helena to Kissimmee. 2 airlines have flights from Helena to Kissimmee on a regular basis. Booking flights from Helena to Kissimmee should not be difficult; the airport handles an average of 0 outbound flights to Kissimmee per day.

  • How long is the flight from Helena to Kissimmee?

    For as low as $334, United Airlines can have you in Kissimmee from Helena in 6h 55m. The distance between Helena and Kissimmee is about 2075 mi.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Helena to Kissimmee (average of $128). Flying from Helena to Kissimmee in October is currently the most expensive (average of $305). 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 2 airlines flying from Helena to Kissimmee

Discover the top 2 airlines that operate flights from Helena 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 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$399Average$623FlexibilityNo cancel feeOn-time69%
DeltaCheapest$460Average$791FlexibilityNo cancel feeOn-timeN/A

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