HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$39+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 6, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$67
(Priceline)

One-way from

$39
(Kiwi.com)

Popular in

September

Cheapest in

January

Average price

$119
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. 5% potential increase in price ($10 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 January 2026
Search Deals

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 January 6, 2026.

This Priceline deal was found by Cheapflights users on 1/4. 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.
Thu 1/294:43 pmMCO - BDL
Nonstop2h 53mMultiple Airlines
Mon 2/27:13 pmBDL - MCO
1 stop4h 34mMultiple Airlines
Deal found 1/4$67
This Frontier deal was found by Cheapflights users on 1/5. 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.
Thu 1/224:43 pmMCO - BDL
Nonstop2h 53mFrontier
Sun 1/258:31 pmBDL - MCO
Nonstop3h 13mFrontier
Deal found 1/5$68
This Frontier deal was found by Cheapflights users on 1/5. 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.
Thu 1/158:00 amMCO - BOS
Nonstop3h 10mFrontier
Sun 1/1812:10 pmBOS - MCO
Nonstop3h 29mFrontier
Deal found 1/5$68
This CheapOair deal was found by Cheapflights users on 1/5. 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 1/1511:37 amMCO - BOS
Nonstop3h 01mSpirit Airlines
Tue 1/203:43 pmBOS - MCO
Nonstop3h 26mSpirit Airlines
Deal found 1/5$69
This Priceline deal was found by Cheapflights users on 1/4. 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.
Thu 1/1511:37 amMCO - BOS
Nonstop3h 01mMultiple Airlines
Sun 1/1812:10 pmBOS - MCO
Nonstop3h 29mMultiple Airlines
Deal found 1/4$70
This Super.com deal was found by Cheapflights users on 1/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/168:20 pmMCO - BOS
Nonstop2h 59mSpirit Airlines
Tue 1/203:43 pmBOS - MCO
Nonstop3h 26mSpirit Airlines
Deal found 1/5$71
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 3/46:30 amMCO - BDL
Nonstop2h 53mFrontier
Sat 3/78:08 pmBDL - MCO
Nonstop3h 14mFrontier
Deal found 1/5$72
This Super.com deal was found by Cheapflights users on 1/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/308:20 pmMCO - BOS
Nonstop2h 59mSpirit Airlines
Sat 1/313:43 pmBOS - MCO
Nonstop3h 26mSpirit Airlines
Deal found 1/5$72
This Frontier deal was found by Cheapflights users on 1/6. 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 2/132:39 pmMCO - BDL
Nonstop2h 50mFrontier
Thu 2/1911:02 amBDL - MCO
Nonstop3h 14mFrontier
Deal found 1/6$73
This Priceline deal was found by Cheapflights users on 1/5. 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 1/218:20 pmMCO - BOS
Nonstop2h 59mSpirit Airlines
Sat 1/247:00 amBOS - MCO
Nonstop3h 32mSpirit Airlines
Deal found 1/5$73
This Frontier deal was found by Cheapflights users on 1/5. 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.
Thu 2/197:20 amMCO - BDL
Nonstop2h 57mFrontier
Sun 2/229:10 pmBDL - MCO
Nonstop3h 02mFrontier
Deal found 1/5$74
This CheapOair deal was found by Cheapflights users on 1/6. 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.
Fri 1/3011:37 amMCO - BOS
Nonstop3h 01mSpirit Airlines
Fri 2/63:43 pmBOS - MCO
Nonstop3h 26mSpirit Airlines
Deal found 1/6$74

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 January 6, 2026.
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

Sat 1/24

11:37 am-2:38 pm

Nonstop3h 01m

Boston Logan Intl

Sun 1/25

7:00 am-10:32 am

Nonstop3h 32m

$72

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Sun 2/1

4:43 pm-7:36 pm

Nonstop2h 53m

Hartford Bradley Intl

Sat 2/7

8:01 pm-11:15 pm

Nonstop3h 14m

$103

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 1/23

7:03 pm-11:16 pm

1 stop4h 13m

Hartford Bradley Intl

Sun 1/25

2:04 pm-7:08 pm

1 stop5h 04m

$114

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Thu 1/22

7:48 pm-11:56 pm

1 stop4h 08m

Hartford Bradley Intl

Sun 1/25

2:04 pm-7:08 pm

1 stop5h 04m

$114

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Mon 3/9

7:00 pm-10:01 pm

Nonstop3h 01m

Boston Logan Intl

Wed 3/11

12:43 pm-4:10 pm

Nonstop3h 27m

$121

OrlandoWorcester

MCO - ORH

MCOORH

Orlando

Thu 1/29

8:20 am-11:05 am

Nonstop2h 45m

Worcester

Mon 2/2

12:00 pm-3:10 pm

Nonstop3h 10m

$123

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Thu 2/26

2:50 pm-11:44 pm

1 stop8h 54m

Boston Logan Intl

Sun 3/1

5:27 am-1:49 pm

1 stop8h 22m

$123

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Wed 1/28

12:14 pm-3:05 pm

Nonstop2h 51m

Hartford Bradley Intl

Sat 1/31

8:05 am-11:34 am

Nonstop3h 29m

$128

OrlandoWorcester

MCO - ORH

MCOORH

Orlando

Fri 1/30

8:20 am-11:05 am

Nonstop2h 45m

Worcester

Sun 2/1

12:00 pm-3:10 pm

Nonstop3h 10m

$136

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 3/27

8:55 am-3:20 pm

1 stop6h 25m

Hartford Bradley Intl

Mon 3/30

6:15 am-9:15 am

Nonstop3h 00m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 60 results
1
2
3
...
6

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, March 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 $101). 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 January 6, 2026.

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 74% versus a flight in the afternoon.

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 January 3, 2026.

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.

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 January 6, 2026.

The most flights from K1S to USMA are scheduled on a Tuesday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 January 6, 2026.
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
8,022 reviews

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
8,022 reviews
Delta
7.9
Good
8,022 reviews

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
11,088 reviews
Delta
7.9
Good
8,022 reviews

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
2,896 reviews
Delta
7.9
Good
8,022 reviews

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
8,283 reviews
Delta
7.9
Good
8,022 reviews

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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
5.7
Fair
3,064 reviews
Delta
7.9
Good
8,022 reviews

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

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 53m. Fly via Spirit Airlines, Frontier, or Breeze Airways to get the fastest option. Airlines will cover a distance of 1050 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 $36 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $39 and Breeze Airways from $51 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 (97%), Spirit Airlines (86%) or Frontier (84%) 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 $578, our data shows the cheapest flight currently is $41. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $66 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, March 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 $101). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kissimmee to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Miami to LaGuardia flights
Orlando to Las Vegas flights
Miami to Newark flights
Fort Lauderdale to Las Vegas flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Tampa to John F Kennedy Intl flights
West Palm Beach to Newark flights
Tampa to LaGuardia flights
Tampa to Newark flights
Orlando to LaGuardia flights
Orlando to Newark flights
West Palm Beach to John F Kennedy Intl flights
Miami to Denver flights
Orlando to Los Angeles flights
Orlando to Denver flights
Orlando to Seattle flights
Tampa to Las Vegas flights
Miami to Las Vegas flights
Tampa to Denver flights
Fort Lauderdale to Atlanta flights
Fort Lauderdale to Denver flights
Miami to Los Angeles flights
Tampa to Seattle flights
Miami to Sky Harbor Intl flights
Fort Lauderdale to Sky Harbor Intl flights
Tampa to Atlanta flights
Jacksonville to John F Kennedy Intl flights
Orlando to Dulles Intl flights
West Palm Beach to LaGuardia flights
Miami to Atlanta flights
Tampa to Dulles Intl flights
Tampa to Dallas/Fort Worth flights
Fort Lauderdale to Los Angeles flights
Tampa to Sky Harbor Intl flights
Tampa to Boston flights
Orlando to Sky Harbor Intl flights
Orlando to Hobby flights
Jacksonville to LaGuardia flights
Orlando to Boston flights
Tampa to Reagan-National flights
Orlando to Dallas/Fort Worth flights
West Palm Beach to Atlanta flights
Fort Lauderdale to Dallas/Fort Worth flights
Orlando to San Francisco flights
Fort Lauderdale to Hobby flights
Orlando to White Plains flights

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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$129FlexibilityNo cancel feeOn-time65%
FrontierCheapest$40Average$139FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$53Average$193FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$117Average$311FlexibilityNo cancel feeOn-time62%
DeltaCheapest$117Average$255FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$120Average$263FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$167Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$311FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.