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$80+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Apr 18 — Apr 251
Sat 4/18
Sat 4/25
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 44 days in advance, depart on a Friday or Thursday and return on a Wednesday

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 March 19, 2026.

This Super.com deal was found by Cheapflights users on 3/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MCO
-
BOS
Nonstop3h 12m
Frontier
Wed 5/1310:07 am
BOS
-
MCO
Nonstop3h 23m
Frontier
Deal found 3/16$117
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MCO
-
BOS
Nonstop3h 12m
Frontier
Tue 5/1210:07 am
BOS
-
MCO
Nonstop3h 23m
Frontier
Deal found 3/17$118
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Sat 4/43:10 pm
MCO
-
BOS
Nonstop2h 59m
Spirit Airlines
Tue 4/79:45 am
BOS
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 3/17$124
This Frontier deal was found by Cheapflights users on 3/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/47:45 am
MCO
-
BOS
Nonstop3h 16m
Frontier
Sun 4/511:31 am
BOS
-
MCO
Nonstop3h 24m
Frontier
Deal found 3/16$125
This Kiwi.com deal was found by Cheapflights users on 3/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:25 am
MCO
-
BOS
1 stop17h 01m
Multiple Airlines
Sat 4/47:14 pm
BOS
-
MCO
Nonstop3h 17m
Multiple Airlines
Deal found 3/18$126
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Wed 4/81:55 pm
MCO
-
BOS
Nonstop2h 59m
Multiple Airlines
Wed 4/2911:16 am
BOS
-
MCO
Nonstop3h 24m
Multiple Airlines
Deal found 3/14$127
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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.
Sat 4/43:10 pm
MCO
-
BOS
Nonstop2h 59m
Spirit Airlines
Sun 4/59:45 am
BOS
-
MCO
Nonstop3h 15m
Spirit Airlines
Deal found 3/18$129
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Thu 4/306:30 am
MCO
-
BOS
Nonstop2h 59m
Multiple Airlines
Sun 5/310:53 am
BOS
-
MCO
Nonstop3h 21m
Multiple Airlines
Deal found 3/17$132
This Kiwi.com deal was found by Cheapflights users on 3/15. 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 4/46:57 am
MCO
-
BOS
Nonstop2h 57m
Multiple Airlines
Sun 4/511:31 am
BOS
-
MCO
Nonstop3h 24m
Multiple Airlines
Deal found 3/15$133
This Priceline deal was found by Cheapflights users on 3/14. 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.
Thu 4/306:30 am
MCO
-
BOS
Nonstop2h 59m
Multiple Airlines
Tue 5/510:07 am
BOS
-
MCO
Nonstop3h 23m
Multiple Airlines
Deal found 3/14$134

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 March 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Super.com)

One-way from

$80
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$215
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. 8% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 19, 2026.
Use the filters below to find and compare flights from Kissimmee to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 6/2

5:50 pm-10:40 pm

1 stop4h 50m

Boston Logan Intl

Fri 6/5

3:55 pm-12:15 am

2 stops8h 20m

$252

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 5/23

7:24 am-10:35 am

Nonstop3h 11m

Boston Logan Intl

Tue 5/26

11:34 am-6:01 pm

1 stop6h 27m

$257
Quickest round-trip

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 5/26

12:42 pm-3:47 pm

Nonstop3h 05m

Boston Logan Intl

Thu 5/28

10:25 am-1:33 pm

Nonstop3h 08m

$270

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 5/9

9:35 am-6:45 pm

2 stops9h 10m

Boston Logan Intl

Mon 5/11

10:40 am-7:05 pm

2 stops8h 25m

$278

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 4/30

10:00 am-4:05 pm

1 stop6h 05m

Boston Logan Intl

Mon 5/4

10:40 am-7:05 pm

2 stops8h 25m

$292

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 6/4

3:30 pm-10:50 pm

2 stops7h 20m

Boston Logan Intl

Sat 6/6

2:45 pm-10:40 pm

1 stop7h 55m

$307

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sun 4/5

7:00 am-1:15 pm

1 stop6h 15m

Boston Logan Intl

Thu 4/9

9:05 am-4:43 pm

1 stop7h 38m

$312

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 5/28

8:45 am-5:10 pm

2 stops8h 25m

Boston Logan Intl

Sat 5/30

5:25 am-12:55 pm

2 stops7h 30m

$312

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 6/5

3:30 pm-10:50 pm

2 stops7h 20m

Boston Logan Intl

Tue 6/9

11:35 am-7:30 pm

2 stops7h 55m

$317

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 4/10

7:59 pm-11:01 pm

Nonstop3h 02m

Boston Logan Intl

Sun 4/12

6:00 am-11:57 am

1 stop5h 57m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 22 resultsSorted by cheapest first
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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 March 13, 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 44 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, April is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $48). 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 March 19, 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 70% 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 March 14, 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 March 19, 2026.

The most flights from K1S to BOS are scheduled on a Thursday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).

How much does it cost to fly round-trip from Kissimmee to Boston?

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 March 19, 2026.
Get a feel of what it's like to fly with Delta,JetBlue, andAmerican Airlines 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
8,293 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

7.9

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
8,293 reviews
Delta
7.9
Good
8,293 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

7.9

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
2,909 reviews
Delta
7.9
Good
8,293 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

7.9

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
7.1
Good
11,474 reviews
Delta
7.9
Good
8,293 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

7.9

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
8,528 reviews
Delta
7.9
Good
8,293 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

7.9

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
3,024 reviews
Delta
7.9
Good
8,293 reviews

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

7.9

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 50 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 $270, Southwest can have you in Boston from Kissimmee in 3h 05m. 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 cheapest airlines to fly from Kissimmee to Boston one-way?

    $39 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 Allegiant Air, with prices starting from $41 and $47, 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: Southwest (100%), Korean Air (87%), Japan Airlines( 83%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $495, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $100 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, April is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $48). 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
Concord
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Chelsea
Smithfield
Lincoln
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy

Browse thousands of different options on Cheapflights for your next trip

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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 March 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$136FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$45Average$137FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$53Average$207FlexibilityNo cancel feeOn-time88%
DeltaCheapest$100Average$253FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$102Average$241FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$120Average$278FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$167Average$327FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$319FlexibilityNo cancel feeOn-time69%

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