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Kissimmee

$66+ 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 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
août 4 — août 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Kissimmee are usually found in March or July, booked 15 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Boston to Kissimmee

Keep the following information in mind while searching for Boston to Kissimmee flight deals. Data was last updated juillet 30, 2025.

Round-trip from

$124
(Cheapflightsfares)

One-way from

$66
(CheapOair)

Popular in

June

Cheapest in

March

Average price

$230
From Boston Logan Intl to Kissimmee
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One-way flight from Boston Logan Intl to Kissimmee
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Highest demand for flights based on searches. 0% potential increase in price ($2 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 July 2025
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Find 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 juillet 30, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/232:53 pmBOS - MCO
Nonstop3h 18mSpirit Airlines
dim. 8/246:30 amMCO - BOS
Nonstop3h 09mSpirit Airlines
Deal found 7/30$124
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
ven. 8/229:20 amBOS - MCO
Nonstop3h 18mFrontier
dim. 8/245:30 amMCO - BOS
Nonstop3h 05mFrontier
Deal found 7/29$126
This FlightHub deal was found by Cheapflights users on 7/28. 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.
ven. 8/229:20 amBOS - MCO
Nonstop3h 18mMultiple Airlines
mer. 8/276:30 amMCO - BOS
Nonstop3h 09mMultiple Airlines
Deal found 7/28$131
This Delta deal was found by Cheapflights users on 7/28. 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.
mer. 9/1012:00 pmBOS - MCO
1 stop6h 50mDelta
mer. 9/177:45 pmMCO - BOS
Nonstop3h 01mDelta
Deal found 7/28$167

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 juillet 30, 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

sam. 8/23

2:53 pm-6:11 pm

Nonstop3h 18m

Orlando

dim. 8/24

6:30 am-9:39 am

Nonstop3h 09m

$124

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

ven. 8/22

9:20 am-12:38 pm

Nonstop3h 18m

Orlando

dim. 8/24

5:30 am-8:35 am

Nonstop3h 05m

$126

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

ven. 8/22

9:20 am-12:38 pm

Nonstop3h 18m

Orlando

mar. 8/26

6:30 am-9:39 am

Nonstop3h 09m

$131

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

mer. 9/10

7:05 am-2:25 pm

1 stop7h 20m

Orlando

mar. 9/16

7:45 pm-10:46 pm

Nonstop3h 01m

$167

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

sam. 8/16

4:38 pm-7:57 pm

Nonstop3h 19m

$66

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

dim. 8/24

9:20 am-12:38 pm

Nonstop3h 18m

$67

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

mer. 9/10

11:25 am-5:35 pm

1 stop6h 10m

$89

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

sam. 8/30

5:59 pm-9:24 pm

Nonstop3h 25m

$100

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

ven. 8/29

8:05 am-2:42 pm

1 stop6h 37m

$109

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

mar. 8/26

3:05 pm-6:30 pm

Nonstop3h 25m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 25, 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, May is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $206). Flying from Boston to Kissimmee in November is currently the most expensive (average of $288). 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 juillet 30, 2025.

When flying from Boston to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 July 27, 2025.

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Tuesday mornings when fares are most often at their lowest. Monday mornings 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 juillet 30, 2025.

The most flights from BOS to K1S are scheduled on a Wednesday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 on average).

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

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 juillet 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines 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.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 39 flights from Logan Intl to Kissimmee per day from 10 different airlines.

  • 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 Spirit Airlines ($66), Frontier ($67), and Southwest ($89).

  • 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 Frontier (82%), British Airways (82%) or Azul (76%) 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 $66. While the most popular route (Boston Logan Intl - Orlando) can be booked for $95 on average our data indicates $598 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, May is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $206). Flying from Boston to Kissimmee in November is currently the most expensive (average of $288). 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

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Alternative routes for Boston to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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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 juillet 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$209FlexibilityNo cancel feeOn-time65%
FrontierCheapest$48Average$146FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$51Average$204FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$93Average$283FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$103Average$297FlexibilityNo cancel feeOn-time62%
DeltaCheapest$104Average$313FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$337FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$166Average$261FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$181Average$359FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$192Average$378FlexibilityNo cancel feeOn-time69%

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