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$71+ Cheap flights from Kissimmee, FL to Boston (BOS)

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Boston Logan Intl are usually found in January or February, booked 70 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Kissimmee to Boston

Keep the following information in mind while searching for Kissimmee to Boston flight deals. Data was last updated November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$78
(Kiwi.com)

One-way from

$71
(JetBlue)

Popular in

June

Cheapest in

January

Average price

$157
Provider with most accurate pricing for Orlando (ORL)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Boston Logan Intl flights.
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From Kissimmee to Boston Logan Intl
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One-way flight from Kissimmee to Boston Logan Intl
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Highest demand for flights based on searches. 14% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% 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 Kissimmee to Boston

Cheapest flights from Kissimmee to Boston
Explore the most affordable flight options available from Kissimmee to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

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.
Fri 12/56:45 amMCO - BOS
Nonstop3h 12mMultiple Airlines
Sun 12/78:11 pmBOS - MCO
Nonstop3h 24mMultiple Airlines
Deal found 11/5$78
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/127:00 amMCO - BOS
Nonstop3h 03mSpirit Airlines
Mon 12/1511:08 amBOS - MCO
Nonstop3h 20mSpirit Airlines
Deal found 11/6$79
This Cheapflightsfares deal was found by Cheapflights users on 11/6. 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.
Thu 12/113:59 pmMCO - BOS
Nonstop3h 07mSpirit Airlines
Sun 12/1411:08 amBOS - MCO
Nonstop3h 20mSpirit Airlines
Deal found 11/6$80
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/67:00 amMCO - BOS
Nonstop3h 01mSpirit Airlines
Mon 12/811:08 amBOS - MCO
Nonstop3h 20mSpirit Airlines
Deal found 11/6$81
This Super.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/56:45 amMCO - BOS
Nonstop3h 12mFrontier
Mon 12/811:23 amBOS - MCO
1 stop6h 04mFrontier
Deal found 11/6$83
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.
Thu 12/256:40 amMCO - BOS
Nonstop3h 12mFrontier
Thu 1/811:47 amBOS - MCO
Nonstop3h 33mFrontier
Deal found 11/5$84
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.
Thu 12/256:40 amMCO - BOS
Nonstop3h 12mMultiple Airlines
Wed 12/3112:29 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Deal found 11/5$85
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.
Thu 12/47:00 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Fri 12/1212:17 pmBOS - MCO
Nonstop3h 28mMultiple Airlines
Deal found 11/5$86
This Super.com deal was found by Cheapflights users on 11/6. 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.
Sun 12/217:35 amMCO - BOS
Nonstop3h 06mFrontier
Sat 1/312:22 pmBOS - MCO
Nonstop3h 28mFrontier
Deal found 11/6$87
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:15 amMCO - BOS
Nonstop3h 06mMultiple Airlines
Sat 1/312:29 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Deal found 11/5$89

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Boston 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 6, 2025.
Use the filters below to find and compare flights from Kissimmee to Boston that are best for you.

Fly from

Kissimmee

Fly to

Boston

Route

Depart

Return

Price

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 12/3

3:42 pm-6:44 pm

Nonstop3h 02m

Boston Logan Intl

Mon 12/8

2:59 pm-6:20 pm

Nonstop3h 21m

$116

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 11/21

8:47 pm-9:12 am

1 stop12h 25m

Boston Logan Intl

Mon 11/24

10:59 am-2:24 pm

Nonstop3h 25m

$121

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 12/13

6:00 am-11:59 am

1 stop5h 59m

Boston Logan Intl

Sat 12/13

5:30 pm-9:02 pm

Nonstop3h 32m

$127

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 12/6

9:25 am-2:45 pm

1 stop5h 20m

Boston Logan Intl

Tue 12/9

12:20 pm-7:55 pm

2 stops7h 35m

$128

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 12/3

3:30 pm-10:15 pm

2 stops6h 45m

Boston Logan Intl

Wed 12/10

12:20 pm-5:10 pm

1 stop4h 50m

$128

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 12/27

7:15 am-10:21 am

Nonstop3h 06m

Boston Logan Intl

Wed 12/31

12:29 pm-3:45 pm

Nonstop3h 16m

$136

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 12/16

10:05 am-1:04 pm

Nonstop2h 59m

Boston Logan Intl

Sun 2/1

2:15 pm-5:38 pm

Nonstop3h 23m

$138

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 12/6

3:43 pm-10:26 pm

1 stop6h 43m

Boston Logan Intl

Thu 12/11

6:05 am-12:02 pm

1 stop5h 57m

$140

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 12/4

9:55 am-12:54 pm

Nonstop2h 59m

Boston Logan Intl

Sun 12/7

8:00 am-11:23 am

Nonstop3h 23m

$140

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Mon 12/15

8:20 am-12:55 pm

1 stop4h 35m

Boston Logan Intl

Wed 12/17

12:20 pm-7:55 pm

2 stops7h 35m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 22 results
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Best time to book a flight from Kissimmee to Boston

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

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

Use this chart to determine the optimal time to book a round-trip flight from Kissimmee to Boston. Price data was last updated on October 31, 2025.

The price you pay for your flight from Kissimmee to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 70 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 Kissimmee to Boston?

Currently, February is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $37). Flying from Kissimmee to Boston in July is currently the most expensive (average of $71). 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 K1S to BOS?

Find hourly flight availability from Kissimmee to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Kissimmee to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 57% on your trip compared to booking a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Boston. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Tuesday evenings 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 Kissimmee to Boston

Explore weekly flight availability from Kissimmee to Boston. 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 6, 2025.

The most flights from K1S to BOS are scheduled on a Thursday (60 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (30 on average).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated November 6, 2025.
Get a feel of what it's like to fly with Delta, American Airlines, and JetBlue from Kissimmee to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,040 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,122 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.8
Fair
3,115 reviews
Delta
7.9
Good
8,001 reviews

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

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

    Most people fly into Boston Logan Intl (BOS) if they book a flight to Boston from Kissimmee. On average, Logan Intl has 44 inbound flights from Kissimmee per day from 8 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How long is the flight from Kissimmee to Boston?

    For as low as $116, JetBlue can have you in Boston from Kissimmee in 3h 02m. The distance between Kissimmee and Boston is about 1121 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Before booking your flight to Boston from Kissimmee, check out the most reliable airlines to get you to your destination on time: Korean Air (93%), Japan Airlines (93%), Frontier( 89%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $988, our data shows the cheapest flight currently is $55. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $54 for that flight.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $37). Flying from Kissimmee to Boston in July is currently the most expensive (average of $71). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Alternative routes for Kissimmee to Boston

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Top 8 airlines flying from Kissimmee to Boston

Discover the top 8 airlines that operate flights from Kissimmee to Boston. 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 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$133FlexibilityNo cancel feeOn-time65%
FrontierCheapest$37Average$134FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$53Average$193FlexibilityNo cancel feeOn-time88%
DeltaCheapest$104Average$254FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$114Average$242FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$156Average$272FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$167Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$311FlexibilityNo cancel feeOn-time69%

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