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Kissimmee

$48+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Kissimmee are usually found in March or May, booked 30 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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$85
(FlightHub)

One-way from

$48
(Cheapflightsfares)

Popular in

April

Cheapest in

March

Average price

$228
Provider with most accurate pricing for Boston Logan Intl-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Orlando (ORL) flights.
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From Boston Logan Intl to Kissimmee
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One-way flight from Boston Logan Intl to Kissimmee
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High demand for flights, 2% potential price rise
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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 May 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 May 1, 2025.

This FlightHub deal was found by Cheapflights users on 4/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:00 amBOS - MCO
1 stop4h 52mSpirit Airlines
Wed 6/46:07 amMCO - BOS
Nonstop3h 02mSpirit Airlines
Deal found 4/30$85
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Mon 5/269:40 amBOS - MCO
Nonstop3h 15mMultiple Airlines
Wed 6/46:07 amMCO - BOS
Nonstop3h 02mMultiple Airlines
Deal found 4/29$88
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Tue 5/208:00 amBOS - MCO
Nonstop3h 16mFrontier
Fri 5/305:30 amMCO - BOS
Nonstop3h 10mFrontier
Deal found 4/29$89
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:30 amBOS - MCO
1 stop5h 14mUnited Airlines
Thu 5/84:22 pmMCO - BOS
1 stop7h 37mUnited Airlines
Deal found 4/29$199
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3111:05 amBOS - MCO
1 stop5h 29mAmerican Airlines
Sat 9/1312:03 pmMCO - BOS
1 stop4h 58mAmerican Airlines
Deal found 4/30$223

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 May 1, 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

Wed 5/28

6:00 am-10:52 am

1 stop4h 52m

Orlando

Wed 6/4

6:07 am-9:09 am

Nonstop3h 02m

$85

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 5/20

8:00 am-11:16 am

Nonstop3h 16m

Orlando

Fri 5/30

5:30 am-8:40 am

Nonstop3h 10m

$92

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 5/27

5:45 am-8:52 am

Nonstop3h 07m

Orlando

Fri 5/30

5:30 am-8:40 am

Nonstop3h 10m

$95

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 6/18

5:36 pm-9:04 pm

Nonstop3h 28m

$48

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Fri 5/30

9:40 am-12:55 pm

Nonstop3h 15m

$53

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Tue 7/1

1:16 pm-6:29 pm

1 stop5h 13m

$100

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sun 7/27

10:10 am-1:20 pm

Nonstop3h 10m

$124

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 7/12

5:30 am-10:34 am

1 stop5h 04m

$126

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Wed 6/11

4:25 pm-9:30 pm

1 stop5h 05m

$133

BostonOrlando

BOS - MCO

BOSMCO

Boston Logan Intl

Sat 5/24

12:51 pm-9:00 pm

3 stops32h 09m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 April 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 16 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 $289). 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 May 1, 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 March 30, 2025.

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Tuesday at noon 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 May 1, 2025.

The most flights from BOS to K1S are scheduled on a Tuesday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 May 1, 2025.
See what other customers who have flown with Southwest, United Airlines and JetBlue from Boston to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Spirit Airlines
6.3
Okay
7,963 reviews
Southwest
8.0
Very good
4,294 reviews

Food

7.1

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 31 flights from Logan Intl to Kissimmee per day from 9 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 Frontier ($48), Spirit Airlines ($54), and United Airlines ($100).

  • 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 Air France (87%), American Airlines (83%) or KLM (83%) 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 $47. While the most popular route (Boston Logan Intl - Orlando) can be booked for $79 on average our data indicates $480 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 $289). 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.

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Top 9 airlines flying from Boston to Kissimmee

Discover the top 9 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$199FlexibilityNo cancel feeOn-time65%
FrontierCheapest$41Average$156FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$66Average$208FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$93Average$283FlexibilityNo cancel feeOn-time88%
DeltaCheapest$108Average$317FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$110Average$301FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$168Average$345FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$200Average$399FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$206Average$415FlexibilityNo cancel feeOn-time63%

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