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$44+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheapflights Tip: The best prices from Kissimmee to Boston Logan Intl are usually found in February or March, 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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$80
(FlightHub)

One-way from

$44
(FlightHub)

Popular in

July

Cheapest in

February

Average price

$147
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. 12% potential increase in price ($23 potential increase over avg. RT price).
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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 March 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 March 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Thu 4/311:01 amMCO - BOS
Nonstop2h 59mSpirit Airlines
Sun 4/65:15 amBOS - MCO
Nonstop3h 24mSpirit Airlines
Deal found 3/27$80
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Thu 5/19:52 pmMCO - BOS
Nonstop3h 13mMultiple Airlines
Mon 5/59:09 pmBOS - MCO
Nonstop3h 20mMultiple Airlines
Deal found 3/27$90
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Thu 5/89:52 pmMCO - BOS
Nonstop3h 13mFrontier
Sun 5/116:00 amBOS - MCO
Nonstop3h 15mFrontier
Deal found 3/27$96
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/228:55 amMCO - BOS
Nonstop3h 04mJetBlue
Tue 5/276:10 pmBOS - MCO
Nonstop3h 23mJetBlue
Deal found 3/27$137
This American Airlines deal was found by Cheapflights users on 3/26. 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.
Sat 5/246:38 pmMCO - BOS
1 stop5h 41mAmerican Airlines
Tue 5/2710:46 amBOS - MCO
1 stop6h 43mAmerican Airlines
Deal found 3/26$188
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/114:30 pmMCO - BOS
2 stops6h 45mSouthwest
Mon 4/147:35 amBOS - MCO
1 stop7h 35mSouthwest
Deal found 3/27$212

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 28, 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 4/9

9:36 am-12:36 pm

Nonstop3h 00m

Boston Logan Intl

Mon 4/14

9:39 pm-12:59 am

Nonstop3h 20m

$80

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 5/1

9:52 pm-1:05 am

Nonstop3h 13m

Boston Logan Intl

Mon 5/5

9:09 pm-12:29 am

Nonstop3h 20m

$90

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 5/8

9:52 pm-1:05 am

Nonstop3h 13m

Boston Logan Intl

Sun 5/11

6:00 am-9:15 am

Nonstop3h 15m

$96

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 5/22

8:55 am-11:59 am

Nonstop3h 04m

Boston Logan Intl

Tue 5/27

6:10 pm-9:33 pm

Nonstop3h 23m

$137

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 5/24

5:00 am-11:09 am

1 stop6h 09m

Boston Logan Intl

Mon 5/26

5:55 am-12:14 pm

1 stop6h 19m

$188

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 4/11

4:30 pm-11:15 pm

2 stops6h 45m

Boston Logan Intl

Wed 4/16

7:30 am-2:25 pm

2 stops6h 55m

$207

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 4/9

9:39 am-6:14 pm

1 stop8h 35m

$47

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 4/5

9:30 pm-12:47 am

Nonstop3h 17m

$49

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 5/22

6:12 pm-9:20 pm

Nonstop3h 08m

$69

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Mon 4/7

7:35 pm-12:30 am

1 stop4h 55m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 16 results
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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 March 21, 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 March 28, 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 23, 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 March 28, 2025.

The most flights from K1S to BOS are scheduled on a Thursday (71 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 March 28, 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
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 31 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?

    $44 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 JetBlue, with prices starting from $49 and $69, 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: ITA Airways (100%), Korean Air (93%), Japan Airlines( 93%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $1,541, our data shows the cheapest flight currently is $39. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $24 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
Warwick
Marlborough
Waltham
Cambridge
Framingham
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
West Yarmouth
Woburn
Somerville
Saco
Burlington
Smithfield
Salem
Chelsea
Seabrook
Brookline

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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$117FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$44Average$152FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$75Average$178FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$92Average$146FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$101Average$244FlexibilityNo cancel feeOn-time62%
DeltaCheapest$104Average$278FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$376FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$366FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$396FlexibilityNo cancel feeOn-time69%
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