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$59+ 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 4/4. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Boston Logan Intl are usually found in January or March, booked 70 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap 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 February 12, 2026.

This Expedia deal was found by Cheapflights users on 2/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:50 am
MCO
-
BOS
Nonstop2h 58m
Spirit Airlines
Tue 3/179:45 am
BOS
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 2/10$73
This Expedia deal was found by Cheapflights users on 2/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:00 pm
MCO
-
BOS
Nonstop3h 01m
Spirit Airlines
Tue 3/179:45 am
BOS
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 2/9$78
This Expedia deal was found by Cheapflights users on 2/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:00 pm
MCO
-
BOS
Nonstop3h 01m
Spirit Airlines
Tue 3/104:22 pm
BOS
-
MCO
Nonstop3h 28m
Spirit Airlines
Deal found 2/9$80
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:50 am
MCO
-
BOS
Nonstop2h 58m
Spirit Airlines
Tue 3/1012:43 pm
BOS
-
MCO
Nonstop3h 27m
Spirit Airlines
Deal found 2/10$81
This Expedia deal was found by Cheapflights users on 2/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:50 am
MCO
-
BOS
Nonstop2h 58m
Spirit Airlines
Sun 3/84:22 pm
BOS
-
MCO
Nonstop3h 28m
Spirit Airlines
Deal found 2/11$82
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Tue 5/127:05 am
MCO
-
BOS
Nonstop3h 16m
Multiple Airlines
Sat 5/167:00 am
BOS
-
MCO
Nonstop3h 10m
Multiple Airlines
Deal found 2/11$83
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:05 am
MCO
-
BOS
Nonstop3h 16m
Frontier
Mon 5/1811:16 am
BOS
-
MCO
Nonstop3h 24m
Frontier
Deal found 2/10$85
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:50 am
MCO
-
BOS
Nonstop2h 58m
Spirit Airlines
Wed 3/44:22 pm
BOS
-
MCO
Nonstop3h 28m
Spirit Airlines
Deal found 2/9$86
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:05 am
MCO
-
BOS
Nonstop3h 16m
Frontier
Mon 5/1111:16 am
BOS
-
MCO
Nonstop3h 24m
Frontier
Deal found 2/9$87
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
MCO
-
BOS
Nonstop3h 06m
Multiple Airlines
Sun 3/812:43 pm
BOS
-
MCO
Nonstop3h 27m
Multiple Airlines
Deal found 2/9$89
This Spirit deal was found by Cheapflights users on 2/11. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:00 pm
MCO
-
BOS
Nonstop3h 01m
Spirit Airlines
Sun 3/84:22 pm
BOS
-
MCO
Nonstop3h 28m
Spirit Airlines
Deal found 2/11$90

Find flight deals from Kissimmee to Boston

Keep the following information in mind while searching for Kissimmee to Boston flight deals. Data was last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$73
(Expedia)

One-way from

$59
(Vakatrip)

Popular in

June

Cheapest in

January

Average price

$162
Provider with most accurate pricing for Orlando (ORL)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Boston Logan Intl flights.
Search Deals
From Kissimmee to Boston Logan Intl
Search Deals
One-way flight from Kissimmee to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 12, 2026.
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

Thu 3/12

6:33 pm-9:33 pm

Nonstop3h 00m

Boston Logan Intl

Sun 3/15

4:23 pm-7:36 pm

Nonstop3h 13m

$125

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 3/12

6:33 pm-9:33 pm

Nonstop3h 00m

Boston Logan Intl

Sat 3/21

7:14 pm-10:31 pm

Nonstop3h 17m

$139

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 2/25

7:05 am-10:07 am

Nonstop3h 02m

Boston Logan Intl

Sun 3/1

7:54 pm-11:26 pm

Nonstop3h 32m

$197

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 6/4

7:24 am-10:35 am

Nonstop3h 11m

Boston Logan Intl

Sat 6/6

6:00 am-12:51 pm

1 stop6h 51m

$207

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 5/28

7:05 am-2:15 pm

1 stop7h 10m

Boston Logan Intl

Thu 6/4

8:20 pm-11:39 pm

Nonstop3h 19m

$217

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 6/4

7:24 am-10:35 am

Nonstop3h 11m

Boston Logan Intl

Mon 6/8

11:05 am-5:26 pm

1 stop6h 21m

$217

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 2/26

5:58 pm-10:48 pm

1 stop4h 50m

Boston Logan Intl

Sun 3/1

11:00 am-6:51 pm

1 stop7h 51m

$217

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 5/23

4:15 pm-10:18 pm

1 stop6h 03m

Boston Logan Intl

Sat 6/6

3:00 pm-9:52 pm

1 stop6h 52m

$217

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sun 5/31

7:00 am-10:05 am

Nonstop3h 05m

Boston Logan Intl

Sat 6/6

8:30 pm-11:41 pm

Nonstop3h 11m

$227

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 5/5

7:00 am-2:21 pm

1 stop7h 21m

Boston Logan Intl

Tue 5/5

6:50 pm-12:06 am

1 stop5h 16m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 23 results
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2
3

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 February 6, 2026.

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, March is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $38). 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 February 12, 2026.

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 71% 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 February 7, 2026.

Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Saturday 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 February 12, 2026.

The most flights from K1S to BOS are scheduled on a Wednesday (56 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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 February 12, 2026.
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
8,191 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
8,191 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
11,277 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
2,897 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
8,451 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
5.7
Fair
3,052 reviews
Delta
7.9
Good
8,191 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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 21 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 $125, Spirit Airlines can have you in Boston from Kissimmee in 3h. The distance between Kissimmee and Boston is about 1121 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Kissimmee to Boston one-way?

    $36 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Breeze Airways, with prices starting from $39 and $51, respectively.

  • 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: Japan Airlines (93%), Frontier (91%), Korean Air( 89%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $989, 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 $70 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, March is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $38). 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Concord
Seabrook
Cranston
Lincoln
Warwick
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell

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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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$126FlexibilityNo cancel feeOn-time65%
FrontierCheapest$37Average$132FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$53Average$207FlexibilityNo cancel feeOn-time88%
DeltaCheapest$94Average$247FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$95Average$238FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$120Average$263FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$167Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$311FlexibilityNo cancel feeOn-time69%

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