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Kissimmee

$39+ Cheap flights from Boston (BOS) 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from Boston Logan Intl to Kissimmee are usually found in March or May, booked 30 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Boston to Kissimmee

Keep the following information in mind while searching for Boston to Kissimmee flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$75
(Cheapflightsfares)

One-way from

$39
(Cheapflightsfares)

Popular in

April

Cheapest in

March

Average price

$273
Provider with most accurate pricing for Boston Logan Intl-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Orlando (ORL) flights.
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From Boston Logan Intl to Kissimmee
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One-way flight from Boston Logan Intl to Kissimmee
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Boston to Kissimmee

Cheapest flights from Boston to Kissimmee
Explore the most affordable flight options available from Boston to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on febrero 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/75:45 amBOS - MCO
Nonstop3h 24mSpirit Airlines
mar. 3/1110:04 amMCO - BOS
Nonstop2h 57mSpirit Airlines
Deal found 2/20$75
This Flightnetwork deal was found by Cheapflights users on 2/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/110:02 pmBOS - MCO
1 stop9h 46mMultiple Airlines
mar. 4/89:30 pmMCO - BOS
Nonstop3h 17mMultiple Airlines
Deal found 2/19$77
This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/76:00 amBOS - MCO
Nonstop3h 32mFrontier
lun. 4/149:30 pmMCO - BOS
Nonstop3h 17mFrontier
Deal found 2/20$78
This Delta deal was found by Cheapflights users on 2/20. 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.
sáb. 3/17:50 pmBOS - MCO
Nonstop3h 28mDelta
jue. 3/67:05 amMCO - BOS
Nonstop3h 00mDelta
Deal found 2/20$137
This JetBlue deal was found by Cheapflights users on 2/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 3/79:59 pmBOS - MCO
Nonstop3h 18mJetBlue
mar. 3/117:00 amMCO - BOS
Nonstop3h 00mJetBlue
Deal found 2/19$167

Find flights from Boston to Kissimmee within your budget

Customize your flight search to find flights from Boston 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 febrero 20, 2025.

Fly from

Boston

Fly to

Kissimmee

Route

Depart

Return

Price

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

vie. 3/7

5:45 am-9:09 am

Nonstop3h 24m

Orlando

mar. 3/11

10:04 am-1:01 pm

Nonstop2h 57m

$75

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

dom. 3/2

6:00 am-9:34 am

Nonstop3h 34m

Orlando

mié. 3/12

1:13 pm-4:12 pm

Nonstop2h 59m

$76

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

lun. 4/7

6:00 am-9:32 am

Nonstop3h 32m

Orlando

lun. 4/14

9:30 pm-12:47 am

Nonstop3h 17m

$78

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

sáb. 3/1

7:50 pm-11:18 pm

Nonstop3h 28m

Orlando

mar. 3/4

7:05 am-10:05 am

Nonstop3h 00m

$137

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

vie. 3/7

9:59 pm-1:17 am

Nonstop3h 18m

Orlando

mar. 3/11

7:00 am-10:00 am

Nonstop3h 00m

$167

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

dom. 4/6

6:00 am-9:32 am

Nonstop3h 32m

$39

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

mar. 3/25

8:00 am-5:49 pm

1 stop9h 49m

$41

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

jue. 2/27

8:59 pm-12:17 am

Nonstop3h 18m

$79

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

jue. 2/27

10:05 am-5:24 pm

1 stop7h 19m

$89

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

jue. 5/8

6:00 am-10:59 pm

2 stops16h 59m

$97

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 14 results
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Best time to book a flight from Boston to Kissimmee

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

Travel insights for flights from Boston to Kissimmee

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

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

Use this chart to determine the optimal time to book a round-trip flight from Boston to Kissimmee. Price data was last updated on February 14, 2025.

The price you pay for your flight from Boston to Kissimmee may vary depending on when you book. For the best chance of a lower fare, look to book 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, May is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $206). Flying from Boston to Kissimmee in November is currently the most expensive (average of $289). 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 BOS to K1S?

Find hourly flight availability from Boston 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 febrero 20, 2025.

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

What is the cheapest day to fly from Boston to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Boston to Kissimmee. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Kissimmee

Explore weekly flight availability from Boston to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated febrero 20, 2025.

The most flights from BOS to K1S are scheduled on a Monday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 febrero 20, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta from Boston to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

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

    If you book a flight to Kissimmee from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 55 flights from Logan Intl to Kissimmee per day from 9 different airlines.

  • What are the cheapest airlines to fly from Boston to Kissimmee one-way?

    The cheapest airlines for a one-way flight from Boston to Kissimmee are Frontier ($39), Spirit Airlines ($42), and Delta ($69).

  • What are the most reliable airlines from Boston to Kissimmee?

    No one likes to see their flight delayed. When booking a flight from Boston to Kissimmee consider choosing American Airlines (100%), Air France (83%) or Scandinavian Airlines (76%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Kissimmee?

    Looking at all options, your cheapest flight can be booked for $35. While the most popular route (Boston Logan Intl - Orlando) can be booked for $39 on average our data indicates $535 when flying from Boston to Kissimmee.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $206). Flying from Boston to Kissimmee in November is currently the most expensive (average of $289). 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 9 airlines flying from Boston to Kissimmee

Discover the top 9 airlines that operate flights from Boston 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$42Average$148FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$61Average$204FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$85Average$282FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$93Average$284FlexibilityNo cancel feeOn-time88%
DeltaCheapest$113Average$337FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$114Average$277FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$174Average$344FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$210Average$370FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$271Average$498FlexibilityNo cancel feeOn-time63%
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