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Kissimmee

$68+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
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 November 5, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$127
(Delta)

One-way from

$68
(Kiwi.com)

Popular in

June

Cheapest in

March

Average price

$302
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, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 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 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 November 5, 2025.

This Super.com deal was found by Cheapflights users on 11/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/159:23 amBOS - MCO
Nonstop3h 20mFrontier
Mon 11/247:00 amMCO - BOS
Nonstop3h 04mFrontier
Deal found 11/5$124
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/88:28 amBOS - MCO
2 stops8h 59mMultiple Airlines
Sat 12/137:00 amMCO - BOS
Nonstop3h 01mMultiple Airlines
Deal found 11/5$125
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Thu 11/205:45 pmBOS - MCO
Nonstop3h 21mSpirit Airlines
Wed 11/266:40 pmMCO - BOS
1 stop4h 17mSpirit Airlines
Deal found 11/4$127
This Frontier deal was found by Cheapflights users on 11/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/159:23 amBOS - MCO
Nonstop3h 20mFrontier
Tue 11/257:00 amMCO - BOS
Nonstop3h 04mFrontier
Deal found 11/5$128
This Priceline deal was found by Cheapflights users on 11/4. 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.
Mon 11/2410:59 amBOS - MCO
Nonstop3h 25mMultiple Airlines
Wed 11/261:52 pmMCO - BOS
Nonstop2h 58mMultiple Airlines
Deal found 11/4$129
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sun 11/2310:46 amBOS - MCO
Nonstop3h 25mMultiple Airlines
Thu 11/271:52 pmMCO - BOS
Nonstop2h 58mMultiple Airlines
Deal found 11/4$130
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Mon 12/85:45 amBOS - MCO
1 stop11h 44mSpirit Airlines
Fri 12/126:34 pmMCO - BOS
1 stop5h 22mSpirit Airlines
Deal found 11/4$131
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Sun 12/75:45 amBOS - MCO
1 stop11h 44mSpirit Airlines
Mon 12/153:59 pmMCO - BOS
Nonstop3h 07mSpirit Airlines
Deal found 11/4$132
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Tue 12/29:54 pmBOS - MCO
2 stops16h 48mSpirit Airlines
Sat 12/67:00 amMCO - BOS
Nonstop3h 01mSpirit Airlines
Deal found 11/4$133
This Cheapflightsfares deal was found by Cheapflights users on 11/4. 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.
Mon 12/15:45 pmBOS - MCO
Nonstop3h 21mSpirit Airlines
Wed 12/31:52 pmMCO - BOS
Nonstop2h 58mSpirit Airlines
Deal found 11/4$134
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Tue 12/25:45 pmBOS - MCO
Nonstop3h 21mSpirit Airlines
Mon 12/87:00 amMCO - BOS
Nonstop3h 03mSpirit Airlines
Deal found 11/4$135
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Tue 11/1812:00 pmBOS - MCO
1 stop7h 23mMultiple Airlines
Mon 11/247:00 amMCO - BOS
Nonstop3h 04mMultiple Airlines
Deal found 11/4$136

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 November 5, 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

Sat 12/6

12:45 pm-5:55 pm

1 stop5h 10m

Orlando

Wed 12/10

2:10 pm-9:40 pm

1 stop7h 30m

$127

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Fri 1/9

6:00 am-5:27 pm

1 stop11h 27m

Orlando

Sun 1/18

5:15 am-7:52 am

1 stop26h 37m

$138

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 12/6

5:05 pm-10:50 pm

1 stop5h 45m

Orlando

Sat 12/13

7:00 am-2:27 pm

1 stop7h 27m

$147

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 12/2

5:13 pm-11:47 pm

1 stop6h 34m

Orlando

Wed 12/3

6:35 pm-1:27 am

1 stop6h 52m

$147

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 1/14

7:30 pm-10:55 pm

Nonstop3h 25m

Orlando

Sun 1/18

6:00 am-8:58 am

Nonstop2h 58m

$154

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Fri 1/9

2:15 pm-5:38 pm

Nonstop3h 23m

Orlando

Sun 1/18

6:00 am-8:58 am

Nonstop2h 58m

$154

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 1/17

6:00 pm-9:29 pm

Nonstop3h 29m

Orlando

Mon 1/26

6:59 pm-10:01 pm

Nonstop3h 02m

$154

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Mon 12/15

1:35 pm-8:10 pm

1 stop6h 35m

Orlando

Tue 12/16

6:30 am-12:55 pm

1 stop6h 25m

$157

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Thu 1/22

3:43 pm-7:09 pm

Nonstop3h 26m

Orlando

Sun 1/25

11:00 pm-1:04 am

2 stops26h 04m

$160

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 1/17

10:05 am-3:29 pm

1 stop5h 24m

Orlando

Sat 1/24

6:00 am-12:15 pm

1 stop6h 15m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 21 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.

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 October 31, 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, March is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $38). Flying from Boston to Kissimmee in June is currently the most expensive (average of $87). 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 November 5, 2025.

One of the essential ways to save on airfare from Boston to Kissimmee is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 9% on airfare.

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 November 2, 2025.

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Wednesday afternoons 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 November 5, 2025.

The most flights from BOS to K1S are scheduled on a Monday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

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 November 5, 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
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

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
8,004 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

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
11,042 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

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
2,907 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

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
8,115 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

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
3,116 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

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 32 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 5h 10m. The distance from Boston to Kissimmee is about 1121 mi. This flight may include one or multiple stops.

  • 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 Southwest ($69), JetBlue ($74), and Delta ($74).

  • 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 Spirit Airlines (86%), Icelandair (82%) or Aeromexico (81%) 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 $68. While the most popular route (Boston Logan Intl - Orlando) can be booked for $54 on average, our data indicates $504 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, March is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $38). Flying from Boston to Kissimmee in June is currently the most expensive (average of $87). 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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$201FlexibilityNo cancel feeOn-time65%
FrontierCheapest$49Average$152FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$51Average$181FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$93Average$255FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$110Average$295FlexibilityNo cancel feeOn-time62%
DeltaCheapest$117Average$319FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$120Average$324FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$166Average$261FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$167Average$360FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$299FlexibilityNo cancel feeOn-time69%

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