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$66+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$86
(Kiwi.com)

One-way from

$66
(Frontier)

Popular in

June

Cheapest in

January

Average price

$197
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. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/11. 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.
Fri 10/315:25 amMCO - BOS
Nonstop3h 03mFrontier
Mon 11/108:58 amBOS - MCO
Nonstop3h 20mFrontier
Deal found 10/11$86
This CheapOair deal was found by Cheapflights users on 10/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:25 amMCO - BOS
Nonstop3h 03mFrontier
Mon 11/108:40 amBOS - MCO
1 stop8h 12mFrontier
Deal found 10/11$93
This Priceline deal was found by Cheapflights users on 10/14. 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.
Fri 11/75:25 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Mon 11/1012:59 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Deal found 10/14$94
This Cheapflightsfares deal was found by Cheapflights users on 10/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/89:42 amMCO - BOS
Nonstop2h 59mSpirit Airlines
Mon 11/1012:59 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 10/12$96
This Orbitz deal was found by Cheapflights users on 10/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:25 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Mon 11/312:59 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Deal found 10/13$99
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 11/85:25 amMCO - BOS
Nonstop3h 03mFrontier
Mon 11/1012:20 pmBOS - MCO
1 stop9h 07mFrontier
Deal found 10/14$100
This Priceline deal was found by Cheapflights users on 10/14. 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 11/87:10 amMCO - BOS
1 stop7h 50mSpirit Airlines
Sat 11/151:36 pmBOS - MCO
Nonstop3h 18mSpirit Airlines
Deal found 10/14$101
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/85:25 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Sun 11/1612:59 pmBOS - MCO
Nonstop3h 16mMultiple Airlines
Deal found 10/12$102
This Priceline deal was found by Cheapflights users on 10/14. 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.
Fri 10/315:25 amMCO - BOS
Nonstop3h 03mFrontier
Mon 11/38:40 amBOS - MCO
1 stop8h 12mFrontier
Deal found 10/14$103
This Orbitz deal was found by Cheapflights users on 10/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:25 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Tue 11/412:00 pmBOS - MCO
1 stop7h 23mMultiple Airlines
Deal found 10/13$104
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:30 pmMCO - BOS
Nonstop3h 07mMultiple Airlines
Sun 12/1411:06 amBOS - MCO
Nonstop3h 33mMultiple Airlines
Deal found 10/12$105

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 October 14, 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

Sat 11/8

7:00 am-10:05 am

Nonstop3h 05m

Boston Logan Intl

Wed 11/12

7:22 pm-10:49 pm

Nonstop3h 27m

$147

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 11/5

12:00 pm-2:55 pm

Nonstop2h 55m

Boston Logan Intl

Tue 11/18

10:05 am-1:20 pm

Nonstop3h 15m

$147

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 11/7

7:00 am-10:05 am

Nonstop3h 05m

Boston Logan Intl

Tue 11/18

7:21 pm-10:45 pm

Nonstop3h 24m

$147

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 11/5

2:00 pm-5:02 pm

Nonstop3h 02m

Boston Logan Intl

Sun 11/16

4:20 pm-7:45 pm

Nonstop3h 25m

$147

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 11/5

7:59 pm-10:59 pm

Nonstop3h 00m

Boston Logan Intl

Thu 11/13

9:59 am-4:32 pm

1 stop6h 33m

$157

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 10/28

6:05 am-12:00 pm

1 stop5h 55m

Boston Logan Intl

Tue 10/28

6:10 pm-9:34 pm

Nonstop3h 24m

$157

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 10/30

7:05 am-2:16 pm

1 stop7h 11m

Boston Logan Intl

Sun 11/2

7:00 am-10:20 am

Nonstop3h 20m

$157

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 11/5

12:16 pm-5:52 pm

1 stop5h 36m

Boston Logan Intl

Wed 11/12

3:10 pm-6:39 pm

Nonstop3h 29m

$157

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 11/1

2:00 pm-5:02 pm

Nonstop3h 02m

Boston Logan Intl

Sat 11/1

7:35 pm-10:55 pm

Nonstop3h 20m

$160

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 11/14

6:35 pm-10:55 pm

1 stop4h 20m

Boston Logan Intl

Sun 11/16

6:50 am-2:25 pm

1 stop7h 35m

$162

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 20 results
1
2

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 10, 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 October 14, 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 October 12, 2025.

Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Wednesday 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 October 14, 2025.

The most flights from K1S to BOS are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 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 October 14, 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
8.0
Very good
7,975 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
8.0
Very good
7,975 reviews
Delta
8.0
Very good
7,975 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
11,042 reviews
Delta
8.0
Very good
7,975 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
2,906 reviews
Delta
8.0
Very good
7,975 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
8,096 reviews
Delta
8.0
Very good
7,975 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
3,135 reviews
Delta
8.0
Very good
7,975 reviews

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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 47 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 $147, Delta can have you in Boston from Kissimmee in 2h 55m. The distance between Kissimmee and Boston is about 1121 mi. Generally, flights for this route are nonstop.

  • 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 (92%), ITA Airways (90%), Scandinavian Airlines( 89%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $683, our data shows the cheapest flight currently is $73. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $63 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$132FlexibilityNo cancel feeOn-time65%
FrontierCheapest$39Average$131FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$53Average$206FlexibilityNo cancel feeOn-time88%
DeltaCheapest$101Average$256FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$109Average$240FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$156Average$263FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$167Average$355FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$198Average$292FlexibilityNo cancel feeOn-time69%

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