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$44+ Cheap flights from Kissimmee, FL to Massachusetts

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Kissimmee to Massachusetts

Cheapest flights from Kissimmee to Massachusetts
Explore the most affordable flight options available from Kissimmee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/63:59 pmMCO - BOS
Nonstop3h 07mMultiple Airlines
Sun 12/712:57 pmBOS - MCO
Nonstop3h 28mMultiple Airlines
Deal found 10/30$81
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:25 amMCO - BOS
Nonstop3h 03mFrontier
Mon 11/1712:20 pmBOS - MCO
1 stop27h 49mFrontier
Deal found 10/30$82
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:54 amMCO - BDL
Nonstop2h 47mFrontier
Mon 11/101:36 pmBDL - MCO
Nonstop3h 04mFrontier
Deal found 10/28$83
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:25 amMCO - BOS
Nonstop3h 03mFrontier
Mon 11/178:40 amBOS - MCO
1 stop8h 12mFrontier
Deal found 10/30$83
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:00 amMCO - BOS
Nonstop3h 01mSpirit Airlines
Sat 12/138:11 pmBOS - MCO
Nonstop3h 24mSpirit Airlines
Deal found 10/30$84
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/47:06 pmMCO - BDL
1 stop4h 00mMultiple Airlines
Sun 12/142:03 pmBDL - MCO
Nonstop3h 15mMultiple Airlines
Deal found 10/29$85
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/107:00 amMCO - BOS
Nonstop3h 01mMultiple Airlines
Sun 12/1412:57 pmBOS - MCO
Nonstop3h 28mMultiple Airlines
Deal found 10/29$86
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/145:25 amMCO - BOS
Nonstop3h 03mMultiple Airlines
Sun 11/166:16 amBOS - MCO
1 stop12h 23mMultiple Airlines
Deal found 10/30$87
This Breeze Airways deal was found by Cheapflights users on 10/28. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:06 pmMCO - BDL
1 stop4h 00mBreeze Airways
Mon 12/81:30 pmBDL - MCO
1 stop4h 26mBreeze Airways
Deal found 10/28$88
This CheapOair deal was found by Cheapflights users on 10/29. 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.
Thu 12/115:15 amMCO - BOS
1 stop26h 18mFrontier
Sun 12/1412:57 pmBOS - MCO
Nonstop3h 28mFrontier
Deal found 10/29$88
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:18 amMCO - BDL
Nonstop2h 54mMultiple Airlines
Wed 12/108:05 amBDL - MCO
Nonstop3h 16mMultiple Airlines
Deal found 10/28$90
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/256:40 amMCO - BOS
Nonstop3h 12mFrontier
Mon 1/510:43 amBOS - MCO
1 stop13h 42mFrontier
Deal found 10/29$90

Cheap flight deals from Kissimmee to Massachusetts

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

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$79
(eDestinos)

One-way from

$44
(Breeze Airways)

Popular in

September

Cheapest in

January

Average price

$195
Provider with most accurate pricing for Orlando (ORL)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Boston Logan Intl flights.
Search Deals
From Kissimmee to Massachusetts
Search Deals
One-way flight from Kissimmee to Massachusetts
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Massachusetts 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 October 30, 2025.
Use the filters below to find and compare flights from Kissimmee to Massachusetts that are best for you.

Fly from

Kissimmee

Fly to

Massachusetts

Route

Depart

Return

Price

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 12/25

6:40 am-9:52 am

Nonstop3h 12m

Boston Logan Intl

Fri 1/2

12:29 pm-3:45 pm

Nonstop3h 16m

$121

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 11/21

6:36 pm-10:43 pm

1 stop4h 07m

Hartford Bradley Intl

Mon 11/24

1:30 pm-5:56 pm

1 stop4h 26m

$125

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Wed 12/3

12:01 pm-2:49 pm

Nonstop2h 48m

Hartford Bradley Intl

Sat 12/6

8:05 am-11:21 am

Nonstop3h 16m

$128

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 12/25

6:40 am-9:52 am

Nonstop3h 12m

Boston Logan Intl

Wed 12/31

11:09 am-9:25 pm

1 stop10h 16m

$129

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Wed 12/24

7:32 pm-1:14 am

1 stop5h 42m

Boston Logan Intl

Thu 1/1

12:22 pm-3:50 pm

Nonstop3h 28m

$130

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Wed 11/26

6:35 pm-10:42 pm

1 stop4h 07m

Hartford Bradley Intl

Wed 12/3

8:05 am-11:21 am

Nonstop3h 16m

$139

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 11/21

6:36 pm-10:43 pm

1 stop4h 07m

Hartford Bradley Intl

Tue 11/25

6:00 am-9:16 am

Nonstop3h 16m

$147

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 12/19

7:00 am-10:01 am

Nonstop3h 01m

Boston Logan Intl

Thu 1/1

12:22 pm-3:50 pm

Nonstop3h 28m

$150

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Mon 12/22

6:34 pm-11:57 pm

1 stop5h 23m

Boston Logan Intl

Thu 1/1

12:22 pm-3:50 pm

Nonstop3h 28m

$150

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 12/25

6:40 am-9:52 am

Nonstop3h 12m

Boston Logan Intl

Tue 12/30

12:08 pm-3:36 pm

Nonstop3h 28m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Kissimmee to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts 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 Massachusetts

What is the cheapest month to book a flight from Kissimmee to Massachusetts?

Currently, February is the cheapest month in which you can book a flight from Kissimmee to Massachusetts (average of $37). Flying from Kissimmee to Massachusetts in July is currently the most expensive (average of $100). 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 MA?

Find hourly flight availability from Kissimmee to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

When flying from Kissimmee to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 51% versus a flight at noon.

What is the cheapest day to fly from Kissimmee to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Kissimmee to Massachusetts flight should consider departing on Saturday evenings 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.

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

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated October 30, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Kissimmee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,906 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,116 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.8
Fair
3,122 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Kissimmee to Massachusetts?

    There are many flights that can get you from Kissimmee to Massachusetts in 2h 40m. Fly via Breeze Airways, Frontier, or Southwest to get the fastest option. Airlines will cover a distance of 1073 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $52 on Breeze Airways. Other airlines that offer cheap prices include JetBlue from $67 and Southwest from $72 one-way.

  • What are the most popular routes from Kissimmee to Massachusetts?

    When deciding which route to take from Kissimmee to Massachusetts consider Orlando - Boston Logan Intl, Orlando - Hartford Bradley Intl or Orlando - Albany Intl as they are the most popular.

  • What are the most reliable airlines from Kissimmee to Massachusetts?

    No one likes to see their flight delayed. When booking a flight from Kissimmee to Massachusetts consider choosing Korean Air (95%), Japan Airlines (91%) or Frontier (90%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Kissimmee to Massachusetts?

    While on average a flight from Kissimmee to Massachusetts is generally $1,124, our data shows the cheapest flight currently is $56. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $61 for that flight.

  • Can I find deals for flights from Kissimmee to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Kissimmee to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kissimmee to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kissimmee to Massachusetts.

  • Can I find deals for business class flights from Kissimmee to Massachusetts?

    Yes. Cheapflights offers flight deals from Kissimmee to Massachusetts 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 Massachusetts?

    Currently, February is the cheapest month in which you can book a flight from Kissimmee to Massachusetts (average of $37). Flying from Kissimmee to Massachusetts in July is currently the most expensive (average of $100). 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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Alternative routes for Kissimmee to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Kissimmee to Massachusetts

Discover the top 8 airlines that operate flights from Kissimmee to Massachusetts. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$132FlexibilityNo cancel feeOn-time65%
FrontierCheapest$37Average$132FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$53Average$193FlexibilityNo cancel feeOn-time88%
DeltaCheapest$101Average$253FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$110Average$324FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$156Average$272FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$158Average$335FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$311FlexibilityNo cancel feeOn-time69%

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