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$68+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Kissimmee to Boston Logan Intl are usually found in February or January, booked 70 days in advance, depart on a Friday or Thursday 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 July 1, 2025.

Round-trip from

$113
(Frontier)

One-way from

$68
(Frontier)

Popular in

June

Cheapest in

February

Average price

$222
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. 18% potential increase in price ($40 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 July 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 July 1, 2025.

This Frontier deal was found by Cheapflights users on 7/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/145:30 amMCO - BOS
Nonstop3h 05mFrontier
Sat 7/199:40 amBOS - MCO
Nonstop3h 18mFrontier
Deal found 7/1$113
This FlightHub deal was found by Cheapflights users on 6/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/117:55 pmMCO - BOS
Nonstop3h 08mSpirit Airlines
Sat 7/197:26 pmBOS - MCO
Nonstop3h 31mSpirit Airlines
Deal found 6/29$116
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Fri 7/185:30 amMCO - BOS
Nonstop3h 05mMultiple Airlines
Mon 7/218:35 pmBOS - MCO
Nonstop3h 24mMultiple Airlines
Deal found 7/1$117

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 July 1, 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

Mon 7/14

5:30 am-8:35 am

Nonstop3h 05m

Boston Logan Intl

Sat 7/19

9:40 am-12:58 pm

Nonstop3h 18m

$113

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 7/11

7:55 pm-11:03 pm

Nonstop3h 08m

Boston Logan Intl

Sat 7/19

7:26 pm-10:57 pm

Nonstop3h 31m

$116

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 7/18

5:30 am-8:35 am

Nonstop3h 05m

Boston Logan Intl

Mon 7/21

8:35 pm-11:59 pm

Nonstop3h 24m

$117

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sat 8/9

5:30 am-8:35 am

Nonstop3h 05m

$68

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Sun 7/20

6:00 am-8:58 am

Nonstop2h 58m

$69

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 9/25

9:00 am-4:22 pm

1 stop7h 22m

$84

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 8/26

9:00 am-11:58 am

Nonstop2h 58m

$100

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Mon 9/1

6:15 am-11:08 am

1 stop4h 53m

$110

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 9/23

8:50 am-5:05 pm

2 stops8h 15m

$114

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 7/30

6:10 pm-3:43 pm

2 stops21h 33m

$121

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 June 27, 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 70 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 June is currently the most expensive (average of $306). 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 July 1, 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 June 29, 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 July 1, 2025.

The most flights from K1S to BOS are scheduled on a Monday (55 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (31 on average).

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

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 July 1, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and JetBlue from Kissimmee to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,919 reviews
Southwest
8.0
Very good
4,273 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,273 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Spirit Airlines
6.3
Okay
8,101 reviews
Southwest
8.0
Very good
4,273 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 45 inbound flights from Kissimmee per day from 8 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?

    $68 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and United Airlines, with prices starting from $69 and $84, 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: Japan Airlines (97%), Etihad Airways (92%), Korean Air( 85%).

  • What are the cheapest flights from Kissimmee to Boston?

    While on average a flight from Kissimmee to Boston is generally $1,685, our data shows the cheapest flight currently is $66. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $103 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 June is currently the most expensive (average of $306). 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
Cambridge
Medford
Watertown
Warwick
Seabrook
Waltham
Framingham
Cranston
Randolph
Chestnut Hill
Chelsea
Brockton
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Swansea
Lincoln
Quincy

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Alternative routes for Kissimmee to Boston

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Top 8 airlines flying from Kissimmee to Boston

Discover the top 8 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$122FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$37Average$131FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$53Average$139FlexibilityNo cancel feeOn-time88%
DeltaCheapest$99Average$280FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$102Average$238FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$316FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$357FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$198Average$325FlexibilityNo cancel feeOn-time69%

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