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$53+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Boston Logan Intl are usually found in February or January, booked 21 days in advance, depart on a Friday or Saturday and return on a Tuesday

Cheap flight deals from Kissimmee to Boston

Keep the following information in mind while searching for Kissimmee to Boston flight deals. Data was last updated April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$85
(Cheapflightsfares)

One-way from

$53
(FlightHub)

Popular in

July

Cheapest in

February

Average price

$191
Provider with most accurate pricing for Orlando (ORL)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Boston Logan Intl flights.
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From Kissimmee to Boston Logan Intl
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One-way flight from Kissimmee to Boston Logan Intl
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Highest demand for flights based on searches. 9% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find 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 April 29, 2025.

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.
Wed 5/216:09 pmMCO - BOS
1 stop4h 47mSpirit Airlines
Tue 5/275:42 pmBOS - MCO
Nonstop3h 11mSpirit Airlines
Deal found 4/29$85
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/209:33 pmMCO - BOS
Nonstop3h 11mFrontier
Wed 5/218:00 amBOS - MCO
Nonstop3h 16mFrontier
Deal found 4/29$92
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/46:07 amMCO - BOS
Nonstop3h 02mMultiple Airlines
Mon 6/910:51 amBOS - MCO
Nonstop3h 12mMultiple Airlines
Deal found 4/29$101
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.
Fri 5/1612:10 pmMCO - BOS
1 stop5h 11mUnited Airlines
Sun 5/259:00 amBOS - MCO
1 stop5h 28mUnited Airlines
Deal found 4/29$199

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 April 29, 2025.
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

Wed 5/21

6:09 pm-10:56 pm

1 stop4h 47m

Boston Logan Intl

Tue 5/27

5:42 pm-8:53 pm

Nonstop3h 11m

$85

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 5/20

9:33 pm-12:44 am

Nonstop3h 11m

Boston Logan Intl

Wed 5/21

8:00 am-11:16 am

Nonstop3h 16m

$92

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 6/4

6:07 am-9:09 am

Nonstop3h 02m

Boston Logan Intl

Mon 6/9

10:51 am-2:03 pm

Nonstop3h 12m

$101

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 5/16

12:10 pm-5:21 pm

1 stop5h 11m

Boston Logan Intl

Sun 5/25

9:00 am-2:28 pm

1 stop5h 28m

$199

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 6/27

9:33 pm-9:47 am

1 stop12h 14m

Boston Logan Intl

Mon 6/30

9:02 am-8:43 pm

1 stop11h 41m

$230

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 9/6

12:30 pm-3:35 pm

Nonstop3h 05m

$53

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 5/20

9:33 pm-12:44 am

Nonstop3h 11m

$63

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sun 8/31

5:00 am-9:52 am

1 stop4h 52m

$100

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 6/27

9:33 pm-9:47 am

1 stop12h 14m

$110

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 10/10

6:00 am-9:01 am

Nonstop3h 01m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 15 results
1
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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 April 25, 2025.

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 21 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, January is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $218). Flying from Kissimmee to Boston in July is currently the most expensive (average of $311). 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 April 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kissimmee to Boston as you normally would.

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 30, 2025.

Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday 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 April 29, 2025.

The most flights from K1S to BOS are scheduled on a Tuesday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Boston by month

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

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

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

If weather is an important factor for your trip to Boston, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 April 29, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Kissimmee to Boston to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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!
Delta
8.0
Very good
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,295 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

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 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 30 inbound flights from Kissimmee per day from 9 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

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

    $53 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Allegiant Air, with prices starting from $73 and $110, 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: Korean Air (93%), Japan Airlines (91%), Air France( 90%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $961, our data shows the cheapest flight currently is $51. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $88 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, January is the cheapest month in which you can book a flight from Kissimmee to Boston (average of $218). Flying from Kissimmee to Boston in July is currently the most expensive (average of $311). 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 Kissimmee?

Book flights to Kissimmee if you plan to visit one of these locations
Marlborough
Warwick
Cambridge
Waltham
Framingham
Chestnut Hill
Randolph
Brockton
Lowell
Woburn
Somerville
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Lincoln
Salem
Chelsea
Seabrook

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Top 9 airlines flying from Kissimmee to Boston

Discover the top 9 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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$117FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$40Average$147FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$53Average$186FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$92Average$146FlexibilityNo cancel feeOn-time88%
DeltaCheapest$106Average$297FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$107Average$244FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$186Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$396FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$206Average$376FlexibilityNo cancel feeOn-time63%

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