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$70+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Boston Logan Intl are usually found in February or January, booked 21 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 August 18, 2025.

Round-trip from

$97
(FlightHub)

One-way from

$70
(FlightHub)

Popular in

June

Cheapest in

February

Average price

$196
From Kissimmee to Boston Logan Intl
Search Deals
One-way flight from Kissimmee to Boston Logan Intl
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Highest demand for flights based on searches. 18% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 10/235:30 amMCO - BOS
Nonstop3h 03mFrontier
Sun 10/269:18 amBOS - MCO
Nonstop3h 20mFrontier
Deal found 8/18$95
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/610:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
Sat 9/1312:20 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 8/17$97
This Priceline deal was found by Cheapflights users on 8/17. 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.
Wed 9/1710:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
Mon 9/222:53 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 8/17$99
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 9/410:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
Thu 9/112:53 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 8/17$101
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:55 amMCO - BOS
1 stop17h 45mSpirit Airlines
Sun 11/166:15 amBOS - MCO
Nonstop3h 17mSpirit Airlines
Deal found 8/17$102
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:30 amMCO - BOS
Nonstop3h 03mFrontier
Mon 10/279:18 amBOS - MCO
Nonstop3h 20mFrontier
Deal found 8/16$103
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/1310:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
Sat 9/203:00 pmBOS - MCO
1 stop8h 28mSpirit Airlines
Deal found 8/17$104
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 8/316:30 amMCO - BOS
Nonstop3h 09mSpirit Airlines
Wed 9/310:34 amBOS - MCO
Nonstop3h 13mSpirit Airlines
Deal found 8/17$105
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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.
Fri 11/76:59 pmMCO - BOS
Nonstop3h 09mSpirit Airlines
Sun 11/96:15 amBOS - MCO
Nonstop3h 17mSpirit Airlines
Deal found 8/16$108
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/1110:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
Sat 9/133:00 pmBOS - MCO
1 stop8h 28mSpirit Airlines
Deal found 8/16$109
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
Sun 9/72:53 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 8/16$111

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 August 18, 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

Tue 9/9

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Sat 9/13

3:00 pm-11:28 pm

1 stop8h 28m

$97

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 9/10

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Fri 9/12

2:53 pm-6:09 pm

Nonstop3h 16m

$97

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 10/23

5:30 am-8:33 am

Nonstop3h 03m

Boston Logan Intl

Sun 10/26

9:18 am-12:38 pm

Nonstop3h 20m

$101

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 9/4

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Thu 9/11

2:53 pm-6:09 pm

Nonstop3h 16m

$101

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 11/15

6:55 am-12:40 am

1 stop17h 45m

Boston Logan Intl

Sun 11/16

6:15 am-9:32 am

Nonstop3h 17m

$102

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 9/13

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Sat 9/20

3:00 pm-11:28 pm

1 stop8h 28m

$104

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sun 9/14

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Sat 9/20

3:00 pm-11:28 pm

1 stop8h 28m

$104

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 10/2

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Tue 10/7

12:31 pm-3:49 pm

Nonstop3h 18m

$108

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 11/14

6:59 pm-10:08 pm

Nonstop3h 09m

Boston Logan Intl

Mon 11/17

6:15 am-9:32 am

Nonstop3h 17m

$108

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 10/2

10:42 am-1:48 pm

Nonstop3h 06m

Boston Logan Intl

Wed 10/8

12:31 pm-3:49 pm

Nonstop3h 18m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

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 August 8, 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 21 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, January is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $218). Flying from Kissimmee to Boston in July is currently the most expensive (average of $311). 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 August 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kissimmee to Boston as you normally would.

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 August 17, 2025.

Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday 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 August 18, 2025.

The most flights from K1S to BOS are scheduled on a Saturday (58 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (27 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 August 18, 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
7,981 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

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
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

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
2,915 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

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
8,038 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

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
3,212 reviews
Delta
8.0
Very good
7,981 reviews

Food

7.3

Boarding

8.2

Overall

8.0

Crew

8.5

Entertainment

7.9

Comfort

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 45 inbound flights from Kissimmee per day from 9 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 $101, Spirit Airlines can have you in Boston from Kissimmee in 3h 03m. 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: KLM (100%), Air France (90%), ITA Airways( 90%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $1,049, our data shows the cheapest flight currently is $59. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $85 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, January is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $218). Flying from Kissimmee to Boston in July is currently the most expensive (average of $311). 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
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Swansea
Saugus
Burlington
Braintree

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Top 9 airlines flying from Kissimmee to Boston

Discover the top 9 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$126FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$37Average$128FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$49Average$111FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$53Average$172FlexibilityNo cancel feeOn-time88%
DeltaCheapest$96Average$320FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$97Average$236FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$352FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$176Average$316FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$198Average$325FlexibilityNo cancel feeOn-time69%

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