HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$50+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
jul. 5 — jul. 121
sáb. 7/5
sáb. 7/12
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 junio 30, 2025.

Round-trip from

$92
(Priceline)

One-way from

$50
(CheapOair)

Popular in

April

Cheapest in

January

Average price

$198
From Kissimmee to Massachusetts
Search Deals
One-way flight from Kissimmee to Massachusetts
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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 junio 30, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/298:00 amMCO - BDL
Nonstop2h 49mFrontier
dom. 8/3111:05 amBDL - MCO
Nonstop3h 01mFrontier
Deal found 6/29$92
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/241:07 pmMCO - BDL
1 stop4h 02mMultiple Airlines
lun. 7/288:43 pmBDL - MCO
Nonstop3h 06mMultiple Airlines
Deal found 6/29$108
This Breeze Airways deal was found by Cheapflights users on 6/28. 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.
vie. 8/16:47 pmMCO - BDL
1 stop4h 09mBreeze Airways
mar. 8/56:00 amBDL - MCO
Nonstop2h 54mBreeze Airways
Deal found 6/28$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.
vie. 7/117:55 pmMCO - BOS
Nonstop3h 08mSpirit Airlines
sáb. 7/197:26 pmBOS - MCO
Nonstop3h 31mSpirit Airlines
Deal found 6/29$116
This Justfly.com deal was found by Cheapflights users on 6/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/125:30 amMCO - BOS
Nonstop3h 05mMultiple Airlines
jue. 7/176:15 amBOS - MCO
Nonstop3h 24mMultiple Airlines
Deal found 6/28$123
This Frontier deal was found by Cheapflights users on 6/30. 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.
sáb. 7/125:30 amMCO - BOS
Nonstop3h 05mFrontier
sáb. 7/199:40 amBOS - MCO
Nonstop3h 18mFrontier
Deal found 6/30$127
This FlightHub deal was found by Cheapflights users on 6/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/189:26 amMCO - BDL
1 stop6h 46mSpirit Airlines
sáb. 8/232:45 pmBDL - MCO
Nonstop3h 00mSpirit Airlines
Deal found 6/28$136
This Southwest deal was found by Cheapflights users on 6/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/248:35 amMCO - ALB
Nonstop2h 40mSouthwest
jue. 8/288:40 amALB - MCO
Nonstop2h 55mSouthwest
Deal found 6/28$157
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/277:30 pmMCO - BDL
Nonstop2h 55mJetBlue
dom. 8/313:20 pmBDL - MCO
Nonstop3h 06mJetBlue
Deal found 6/29$159
This Breeze Airways deal was found by Cheapflights users on 6/30. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/118:30 amMCO - ALB
1 stop4h 10mBreeze Airways
dom. 9/141:20 pmALB - MCO
1 stop4h 20mBreeze Airways
Deal found 6/30$163
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/109:00 amMCO - ALB
Nonstop2h 48mJetBlue
jue. 8/215:45 pmALB - MCO
Nonstop3h 05mJetBlue
Deal found 6/29$167
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/289:45 amMCO - ORH
Nonstop2h 54mJetBlue
mar. 9/21:34 pmORH - MCO
Nonstop3h 06mJetBlue
Deal found 6/29$183

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 junio 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

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 8/29

8:00 am-10:49 am

Nonstop2h 49m

Hartford Bradley Intl

dom. 8/31

11:05 am-2:06 pm

Nonstop3h 01m

$92

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

jue. 7/24

1:07 pm-5:09 pm

1 stop4h 02m

Hartford Bradley Intl

lun. 7/28

8:43 pm-11:49 pm

Nonstop3h 06m

$108

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 8/1

6:47 pm-10:56 pm

1 stop4h 09m

Hartford Bradley Intl

mar. 8/5

6:00 am-8:54 am

Nonstop2h 54m

$113

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

vie. 7/11

7:55 pm-11:03 pm

Nonstop3h 08m

Boston Logan Intl

sáb. 7/19

7:26 pm-10:57 pm

Nonstop3h 31m

$116

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

sáb. 7/12

5:30 am-8:35 am

Nonstop3h 05m

Boston Logan Intl

jue. 7/17

6:15 am-9:39 am

Nonstop3h 24m

$123

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

sáb. 7/12

5:30 am-8:35 am

Nonstop3h 05m

Boston Logan Intl

sáb. 7/19

9:40 am-12:58 pm

Nonstop3h 18m

$127

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

lun. 8/18

9:26 am-4:12 pm

1 stop6h 46m

Hartford Bradley Intl

sáb. 8/23

2:45 pm-5:45 pm

Nonstop3h 00m

$136

OrlandoAlbany

MCO - ALB

MCOALB

Orlando

dom. 8/24

8:35 am-11:15 am

Nonstop2h 40m

Albany Intl

jue. 8/28

8:40 am-11:35 am

Nonstop2h 55m

$157

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

mié. 8/27

7:30 pm-10:25 pm

Nonstop2h 55m

Hartford Bradley Intl

dom. 8/31

3:20 pm-6:26 pm

Nonstop3h 06m

$159

OrlandoAlbany

MCO - ALB

MCOALB

Orlando

jue. 9/11

8:30 am-12:40 pm

1 stop4h 10m

Albany Intl

dom. 9/14

1:20 pm-5:40 pm

1 stop4h 20m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 59 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, 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 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 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 junio 30, 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 junio 30, 2025.

The most flights from K1S to USMA are scheduled on a Monday (59 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (41 on average).

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 junio 30, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, Southwest, and Delta 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.
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,278 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,973 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,852 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,920 reviews
Breeze Airways
8.1
Very good
182 reviews

Boarding

8.4

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Entertainment

6.6

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 $50 on Breeze Airways. Other airlines that offer cheap prices include Frontier from $51 and Spirit Airlines from $66 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 Japan Airlines (97%), Etihad Airways (92%) or Korean Air (85%) 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 $1,685, 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 $107 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 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

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.
Miami to John F Kennedy Intl flights
Orlando to John F Kennedy Intl flights
Orlando to LaGuardia flights
Fort Lauderdale to LaGuardia flights
Fort Lauderdale to Newark flights
Orlando to Newark flights
Tampa to John F Kennedy Intl flights
Miami to Newark flights
Miami to LaGuardia flights
Orlando to Seattle flights
Tampa to Seattle flights
Orlando to Las Vegas flights
Orlando to Los Angeles flights
Orlando to Dallas/Fort Worth flights
Tampa to Newark flights
Tampa to LaGuardia flights
Miami to Los Angeles flights
Tampa to Las Vegas flights
Fort Lauderdale to John F Kennedy Intl flights
Fort Lauderdale to Atlanta flights
Fort Lauderdale to Los Angeles flights
Miami to Atlanta flights
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to Seattle flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Boston flights
Fort Lauderdale to O'Hare Intl flights
Orlando to Philadelphia flights
Fort Lauderdale to Las Vegas flights
Fort Lauderdale to Philadelphia flights
Tampa to Boston flights
Orlando to Portland flights
Orlando to Dulles Intl flights
Tampa to Denver flights
Fort Lauderdale to Boston flights
Fort Lauderdale to Dallas/Fort Worth flights
Miami to O'Hare Intl flights
Miami to Philadelphia flights
Tampa to Los Angeles flights
Orlando to Denver flights
Miami to Denver flights
Tampa to Dulles Intl flights
Orlando to Baltimore flights
Fort Lauderdale to Baltimore flights
Miami to Boston flights
Orlando to Atlanta flights
Orlando to Midway flights
Tampa to Sky Harbor Intl flights
Fort Lauderdale to Seattle 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 junio 30, 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$313FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$102Average$371FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$316FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$392FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$198Average$325FlexibilityNo 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.