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Kissimmee

$58+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Kissimmee are usually found in March or January, booked 15 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 September 11, 2025.

Round-trip from

$114
(Kiwi.com)

One-way from

$58
(Cheapflightsfares)

Popular in

April

Cheapest in

March

Average price

$254
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. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:20 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Sat 10/116:06 amMCO - BOS
1 stop5h 20mSpirit Airlines
Deal found 9/11$114
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:20 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Thu 10/235:30 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Deal found 9/11$115
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3012:20 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Sat 10/2510:24 amMCO - BOS
Nonstop2h 56mSpirit Airlines
Deal found 9/11$117
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/228:47 amBOS - MCO
1 stop5h 27mMultiple Airlines
Wed 9/2410:42 amMCO - BOS
Nonstop3h 06mMultiple Airlines
Deal found 9/10$118
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:30 amBOS - MCO
1 stop5h 30mSouthwest
Tue 11/189:30 amMCO - BOS
1 stop7h 50mSouthwest
Deal found 9/11$119
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:47 amBOS - MCO
1 stop5h 32mMultiple Airlines
Tue 9/3010:42 amMCO - BOS
Nonstop3h 06mMultiple Airlines
Deal found 9/11$120
This Mytrip deal was found by Cheapflights users on 9/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:20 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Sat 10/118:15 pmMCO - BOS
1 stop11h 12mMultiple Airlines
Deal found 9/11$121
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:20 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Fri 10/245:30 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Deal found 9/11$122
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/412:20 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Wed 10/1510:24 amMCO - BOS
Nonstop2h 56mSpirit Airlines
Deal found 9/11$124
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:15 amBOS - MCO
1 stop5h 15mSouthwest
Wed 10/294:10 pmMCO - BOS
1 stop6h 05mSouthwest
Deal found 9/9$125
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2712:20 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Fri 10/37:38 pmMCO - BOS
1 stop12h 05mMultiple Airlines
Deal found 9/11$127

Cheapflights Fare Finder

 
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 September 11, 2025.
Use the filters below to find and compare flights from Boston to Kissimmee that are best for you.

Fly from

Boston

Fly to

Kissimmee

Route

Depart

Return

Price

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Thu 10/30

3:45 pm-12:10 am

1 stop8h 25m

Orlando

Sat 11/1

9:05 am-3:20 pm

2 stops6h 15m

$144

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 11/4

7:45 am-7:55 pm

2 stops12h 10m

Orlando

Wed 11/12

6:30 am-12:55 pm

1 stop6h 25m

$157

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Thu 10/30

3:45 pm-9:15 pm

1 stop5h 30m

Orlando

Tue 11/4

3:30 pm-10:15 pm

2 stops6h 45m

$158

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 11/12

2:10 pm-7:40 pm

1 stop5h 30m

Orlando

Sun 11/16

10:10 pm-8:15 am

1 stop10h 05m

$158

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 10/25

6:59 pm-10:20 pm

Nonstop3h 21m

Orlando

Sat 11/1

7:00 am-10:05 am

Nonstop3h 05m

$167

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 10/7

6:10 pm-9:34 pm

Nonstop3h 24m

Orlando

Sun 10/12

7:00 am-10:05 am

Nonstop3h 05m

$167

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 11/1

6:59 pm-10:20 pm

Nonstop3h 21m

Orlando

Sun 11/9

7:00 am-10:03 am

Nonstop3h 03m

$167

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Thu 10/23

3:50 pm-8:55 pm

1 stop5h 05m

Orlando

Tue 10/28

4:10 pm-10:15 pm

1 stop6h 05m

$168

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 11/12

12:20 pm-7:40 pm

1 stop7h 20m

Orlando

Sat 11/15

7:05 am-1:10 pm

1 stop6h 05m

$168

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 10/25

8:15 am-1:30 pm

1 stop5h 15m

Orlando

Wed 10/29

10:45 am-7:20 pm

2 stops8h 35m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 results
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2
3

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.

Cheapflights Insights

Everything you need to know about your flight from Boston to Kissimmee

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 August 29, 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 15 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 September 11, 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 September 7, 2025.

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Tuesday mornings when fares are most often at their lowest. Monday mornings 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 September 11, 2025.

The most flights from BOS to K1S are scheduled on a Thursday (46 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).

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

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 September 11, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Boston 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
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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.
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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.
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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.
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

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 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 34 flights from Logan Intl to Kissimmee per day from 10 different airlines.

  • How long is the flight from Boston to Kissimmee?

    Departing from Boston to Kissimmee will take you 3h 21m. The distance from Boston to Kissimmee is about 1121 mi. This flight may include one or multiple stops.

  • 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 Air France (81%), Frontier (79%) or Delta (77%) 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 $56. While the most popular route (Boston Logan Intl - Orlando) can be booked for $118 on average, our data indicates $379 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.

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Top 10 airlines flying from Boston to Kissimmee

Discover the top 10 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$202FlexibilityNo cancel feeOn-time65%
FrontierCheapest$49Average$148FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$51Average$199FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$93Average$283FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$104Average$297FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$315FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$146Average$355FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$162Average$343FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$166Average$261FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$192Average$348FlexibilityNo cancel feeOn-time69%

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