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$51+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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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 septiembre 17, 2025.

Round-trip from

$86
(Cheapflightsfares)

One-way from

$51
(Breeze Airways)

Popular in

April

Cheapest in

January

Average price

$185
From Kissimmee to Massachusetts
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One-way flight from Kissimmee to Massachusetts
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Highest demand for flights based on searches. 8% potential increase in price ($14 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 September 2025
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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 septiembre 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
mié. 10/110:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
sáb. 10/412:20 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 9/15$86
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
mié. 10/110:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
vie. 10/32:53 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 9/15$91
This Breeze Airways deal was found by Cheapflights users on 9/16. 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.
vie. 10/171:42 pmMCO - BDL
1 stop4h 14mBreeze Airways
lun. 10/206:36 pmBDL - MCO
1 stop4h 23mBreeze Airways
Deal found 9/16$95
This Orbitz deal was found by Cheapflights users on 9/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/177:55 amMCO - BDL
Nonstop2h 49mMultiple Airlines
lun. 10/206:36 pmBDL - MCO
1 stop4h 23mMultiple Airlines
Deal found 9/15$100
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
sáb. 10/410:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
mar. 10/73:00 pmBOS - MCO
1 stop8h 09mSpirit Airlines
Deal found 9/16$100
This Frontier deal was found by Cheapflights users on 9/15. 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.
vie. 10/35:05 pmMCO - BDL
Nonstop2h 52mFrontier
lun. 10/68:52 pmBDL - MCO
Nonstop3h 05mFrontier
Deal found 9/15$102
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
sáb. 11/85:25 amMCO - BOS
Nonstop3h 03mFrontier
lun. 11/108:58 amBOS - MCO
Nonstop3h 20mFrontier
Deal found 9/14$102
This CheapOair deal was found by Cheapflights users on 9/17. 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.
vie. 10/247:55 amMCO - BDL
Nonstop2h 49mFrontier
lun. 10/2711:44 amBDL - MCO
Nonstop3h 07mFrontier
Deal found 9/17$108
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
mié. 10/110:42 amMCO - BOS
Nonstop3h 06mSpirit Airlines
vie. 10/312:15 pmBOS - MCO
Nonstop3h 16mSpirit Airlines
Deal found 9/15$108
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
vie. 10/315:25 amMCO - BOS
Nonstop3h 03mFrontier
lun. 11/39:23 amBOS - MCO
Nonstop3h 20mFrontier
Deal found 9/15$111
This Breeze Airways deal was found by Cheapflights users on 9/15. 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.
jue. 10/167:06 pmMCO - BDL
1 stop4h 00mBreeze Airways
lun. 10/206:36 pmBDL - MCO
1 stop4h 23mBreeze Airways
Deal found 9/15$112
This Breeze Airways deal was found by Cheapflights users on 9/16. 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.
jue. 10/237:06 pmMCO - BDL
1 stop4h 00mBreeze Airways
lun. 10/276:36 pmBDL - MCO
1 stop4h 23mBreeze Airways
Deal found 9/16$114

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 septiembre 17, 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

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

jue. 10/16

7:06 pm-11:06 pm

1 stop4h 00m

Hartford Bradley Intl

lun. 10/20

6:36 pm-10:59 pm

1 stop4h 23m

$112

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

jue. 10/23

7:06 pm-11:06 pm

1 stop4h 00m

Hartford Bradley Intl

lun. 10/27

6:36 pm-10:59 pm

1 stop4h 23m

$114

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 10/24

5:41 pm-9:48 pm

1 stop4h 07m

Hartford Bradley Intl

lun. 10/27

6:36 pm-10:59 pm

1 stop4h 23m

$115

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

jue. 10/2

7:06 pm-11:06 pm

1 stop4h 00m

Hartford Bradley Intl

lun. 10/6

1:25 pm-5:51 pm

1 stop4h 26m

$115

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 10/31

1:42 pm-5:56 pm

1 stop4h 14m

Hartford Bradley Intl

lun. 11/3

6:36 pm-10:59 pm

1 stop4h 23m

$120

OrlandoWorcester

MCO - ORH

MCOORH

Orlando

jue. 10/9

9:53 am-12:42 pm

Nonstop2h 49m

Worcester

lun. 10/13

1:37 pm-4:40 pm

Nonstop3h 03m

$123

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

jue. 11/13

7:06 pm-11:06 pm

1 stop4h 00m

Hartford Bradley Intl

lun. 11/17

1:25 pm-5:51 pm

1 stop4h 26m

$129

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 11/7

5:41 pm-9:48 pm

1 stop4h 07m

Hartford Bradley Intl

lun. 11/10

6:36 pm-10:59 pm

1 stop4h 23m

$130

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

jue. 11/13

7:20 am-10:08 am

Nonstop2h 48m

Hartford Bradley Intl

dom. 11/16

3:41 pm-6:43 pm

Nonstop3h 02m

$137

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 11/7

7:20 am-10:08 am

Nonstop2h 48m

Hartford Bradley Intl

lun. 11/10

3:41 pm-6:43 pm

Nonstop3h 02m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

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, January is the cheapest month in which you can book a flight from Kissimmee to Massachusetts (average of $218). Flying from Kissimmee to Massachusetts 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 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 septiembre 17, 2025.

When flying from Kissimmee to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Kissimmee to Massachusetts

Explore weekly flight availability from Kissimmee to Massachusetts. 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 septiembre 17, 2025.

The most flights from K1S to USMA are scheduled on a Monday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

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 septiembre 17, 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
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
2,914 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
8,023 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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
3,173 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

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 45m. Fly via Breeze Airways, JetBlue, 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 $55 on Breeze Airways. Other airlines that offer cheap prices include JetBlue from $64 and Southwest from $69 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 (92%), Japan Airlines (91%) or Frontier (91%) 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 $1,011, our data shows the cheapest flight currently is $60. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $113 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, January is the cheapest month in which you can book a flight from Kissimmee to Massachusetts (average of $218). Flying from Kissimmee to Massachusetts 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.

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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 9 airlines flying from Kissimmee to Massachusetts

Discover the top 9 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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$37Average$128FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$49Average$111FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$53Average$193FlexibilityNo cancel feeOn-time88%
DeltaCheapest$98Average$312FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$101Average$323FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$355FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$176Average$303FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$198Average$306FlexibilityNo cancel feeOn-time69%

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