HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$58+ Cheap flights from Boston (BOS) to Kissimmee, FL

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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Boston Logan Intl to Kissimmee are usually found in January or March, booked 15 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Boston to Kissimmee

Cheapest flights from Boston to Kissimmee
Explore the most affordable flight options available from Boston to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This Delta deal was found by Cheapflights users on 12/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:15 pmBOS - MCO
1 stop6h 11mDelta
Sat 1/107:05 amMCO - BOS
Nonstop3h 02mDelta
Deal found 12/19$142
This Delta deal was found by Cheapflights users on 12/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:30 amBOS - MCO
1 stop7h 31mDelta
Wed 1/77:05 amMCO - BOS
Nonstop3h 02mDelta
Deal found 12/19$157
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/3111:09 amBOS - MCO
1 stop10h 16mMultiple Airlines
Thu 1/87:05 amMCO - BOS
Nonstop3h 06mMultiple Airlines
Deal found 12/19$176
This Priceline deal was found by Cheapflights users on 12/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 amBOS - MCO
Nonstop3h 25mMultiple Airlines
Wed 1/78:33 amMCO - BOS
Nonstop3h 01mMultiple Airlines
Deal found 12/18$189
This Priceline deal was found by Cheapflights users on 12/19. 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 12/317:04 pmBOS - MCO
Nonstop3h 26mMultiple Airlines
Thu 1/17:00 amMCO - BOS
Nonstop3h 01mMultiple Airlines
Deal found 12/19$202
This Kiwi.com deal was found by Cheapflights users on 12/19. 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 12/3111:09 amBOS - MCO
1 stop10h 16mMultiple Airlines
Tue 1/65:26 amMCO - BOS
1 stop19h 53mMultiple Airlines
Deal found 12/19$209

Find flight deals from Boston to Kissimmee

Keep the following information in mind while searching for Boston to Kissimmee flight deals. Data was last updated December 21, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$94
(Kiwi.com)

One-way from

$58
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$285
Provider with most accurate pricing for Boston Logan Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Orlando (ORL) flights.
Search Deals
From Boston Logan Intl to Kissimmee
Search Deals
One-way flight from Boston Logan Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Kissimmee 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 December 21, 2025.
Use the filters below to find and compare flights from Boston to Kissimmee that are best for you.

Fly from

Boston

Fly to

Kissimmee

Route

Depart

Return

Price

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sun 2/1

7:00 am-10:32 am

Nonstop3h 32m

Orlando

Sun 2/8

10:44 am-5:44 pm

1 stop7h 00m

$106

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Mon 1/12

2:15 pm-5:38 pm

Nonstop3h 23m

Orlando

Wed 1/14

5:30 pm-8:34 pm

Nonstop3h 04m

$127

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sun 1/18

7:30 pm-10:54 pm

Nonstop3h 24m

Orlando

Thu 1/29

6:59 pm-10:00 pm

Nonstop3h 01m

$127

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Fri 2/6

7:30 pm-10:55 pm

Nonstop3h 25m

Orlando

Tue 2/10

6:59 pm-10:01 pm

Nonstop3h 02m

$127

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Fri 1/9

7:00 am-12:40 pm

1 stop5h 40m

Orlando

Fri 1/9

7:59 pm-10:59 pm

Nonstop3h 00m

$137

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 1/7

6:40 pm-10:13 pm

Nonstop3h 33m

Orlando

Tue 1/13

7:05 am-10:07 am

Nonstop3h 02m

$142

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 1/10

10:05 am-4:44 pm

1 stop6h 39m

Orlando

Tue 1/13

4:20 pm-9:29 pm

1 stop5h 09m

$147

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Fri 1/9

10:00 am-4:49 pm

1 stop6h 49m

Orlando

Sun 1/11

7:05 am-10:07 am

Nonstop3h 02m

$152

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Thu 1/8

3:00 pm-9:05 pm

1 stop6h 05m

Orlando

Thu 1/15

11:10 am-3:53 pm

1 stop4h 43m

$162

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 12/31

5:30 am-1:01 pm

1 stop7h 31m

Orlando

Wed 1/7

3:25 pm-9:40 pm

1 stop6h 15m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Boston to Kissimmee

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

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

Use this chart to determine the optimal time to book a round-trip flight from Boston to Kissimmee. Price data was last updated on December 19, 2025.

The price you pay for your flight from Boston to Kissimmee may vary depending on when you book. For the best chance of a lower fare, look to book 15 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 Boston to Kissimmee?

Currently, March is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $38). Flying from Boston to Kissimmee in June is currently the most expensive (average of $88). 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 BOS to K1S?

Find hourly flight availability from Boston to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

One of the essential ways to save on airfare from Boston to Kissimmee is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 9% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Boston to Kissimmee. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Wednesday afternoons 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 Boston to Kissimmee

Explore weekly flight availability from Boston to Kissimmee. 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 December 21, 2025.

The most flights from BOS to K1S are scheduled on a Sunday (65 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (22 on average).

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated December 21, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Boston to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,051 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
JetBlue
7.2
Good
2,896 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Spirit Airlines
6.3
Okay
8,192 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Frontier
5.8
Fair
3,078 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

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

    If you book a flight to Kissimmee from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 48 flights from Logan Intl to Kissimmee per day from 10 different airlines.

  • How long is the flight from Boston to Kissimmee?

    Departing from Boston to Kissimmee will take you 3h 23m. The distance from Boston to Kissimmee is about 1121 mi. This flight may include one or multiple stops.

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

    The cheapest airlines for a one-way flight from Boston to Kissimmee are Frontier ($32), Spirit Airlines ($34), and Allegiant Air ($38).

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

    No one likes to see their flight delayed. When booking a flight from Boston to Kissimmee consider choosing KLM (84%), Aeromexico (81%) or JetBlue (78%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Kissimmee?

    Looking at all options, your cheapest flight can be booked for $41. While the most popular route (Boston Logan Intl - Orlando) can be booked for $54 on average, our data indicates $465 when flying from Boston to Kissimmee.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $38). Flying from Boston to Kissimmee in June is currently the most expensive (average of $88). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Boston to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Orlando flights
Boston to Tampa flights
Hartford to Orlando flights
Boston to West Palm Beach flights
Boston to Fort Myers flights
Boston to Sarasota flights
Hartford to Fort Lauderdale flights
Hartford to Tampa flights
Albany to Orlando flights
Boston to Key West flights
Hartford to Miami flights
Boston to Jacksonville flights
Hartford to West Palm Beach flights
Hartford to Fort Myers flights
Albany to Fort Lauderdale flights
Boston to Daytona Beach flights
Worcester to Orlando flights
Albany to Tampa flights
Boston to St Petersburg flights
Hartford to Sarasota flights
Albany to Miami flights
Worcester to Fort Lauderdale flights
Worcester to Fort Myers flights
Boston to Orlando Sanford Intl flights
Albany to West Palm Beach flights
Hartford to Jacksonville flights
Boston to Pensacola flights
Hartford to Key West flights
Boston to Valparaiso flights
Albany to Sarasota flights
Boston to Panama City flights
Hartford to Daytona Beach flights
Boston to Melbourne flights
Albany to St Petersburg flights
Albany to Key West flights
Hartford to Pensacola flights
Albany to Orlando Sanford Intl flights
Hartford to St Petersburg flights
Hartford to Valparaiso flights
Albany to Jacksonville flights
Albany to Pensacola flights
Boston to Tallahassee flights
Albany to Fort Myers flights
West Tisbury to Orlando flights
Hartford to Panama City flights
Albany to Daytona Beach flights
Worcester to Miami flights
Boston to Gainesville flights

Top 10 airlines flying from Boston to Kissimmee

Discover the top 10 airlines that operate flights from Boston to Kissimmee. 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$153FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$51Average$195FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$54Average$203FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$95Average$235FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$115Average$294FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$309FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$136Average$338FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$166Average$261FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$171Average$370FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$289FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.