HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$48+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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

Discover tips and strategies to find the most affordable flight options for your journey from Kissimmee (K1S) to Massachusetts (USMA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$68
(Cheapflightsfares)

One-way from

$52
(Trip.com)
From Kissimmee to Massachusetts
Search Deals
One-way flight from Kissimmee to Massachusetts
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 21, 2025.

This Frontier deal was found by Cheapflights users on 1/21. 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 2/75:30 amMCO - BDL
Nonstop2h 48mFrontier
Sun 2/910:45 amBDL - MCO
Nonstop3h 14mFrontier
Deal found 1/21$68
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 1/316:24 pmMCO - BDL
1 stop4h 06mMultiple Airlines
Sun 2/210:45 amBDL - MCO
Nonstop3h 14mMultiple Airlines
Deal found 1/20$74
This Priceline deal was found by Cheapflights users on 1/19. 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 1/308:34 pmMCO - BOS
Nonstop3h 01mSpirit Airlines
Sun 2/26:25 amBOS - MCO
Nonstop3h 32mSpirit Airlines
Deal found 1/19$77
This Justfly.com deal was found by Cheapflights users on 1/20. 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.
Tue 1/289:23 pmMCO - BOS
Nonstop3h 04mMultiple Airlines
Tue 2/410:00 amBOS - MCO
Nonstop3h 29mMultiple Airlines
Deal found 1/20$78
This Cheapflightsfares deal was found by Cheapflights users on 1/19. 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 2/19:23 pmMCO - BOS
Nonstop3h 04mFrontier
Wed 2/56:00 amBOS - MCO
Nonstop3h 34mFrontier
Deal found 1/19$81
This Gotogate deal was found by Cheapflights users on 1/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/46:53 pmMCO - BDL
1 stop4h 06mBreeze Airways
Sun 4/62:00 pmBDL - MCO
1 stop4h 19mBreeze Airways
Deal found 1/21$102
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/76:09 amMCO - BDL
1 stop10h 56mSpirit Airlines
Sun 2/96:00 pmBDL - MCO
1 stop14h 07mSpirit Airlines
Deal found 1/20$113
This JetBlue Airways deal was found by Cheapflights users on 1/20. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/188:59 pmMCO - ALB
Nonstop2h 50mJetBlue
Tue 2/256:00 amALB - MCO
Nonstop3h 17mJetBlue
Deal found 1/20$157
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/147:35 pmMCO - ALB
1 stop4h 38mAmerican Airlines
Mon 2/245:18 pmALB - MCO
1 stop7h 13mAmerican Airlines
Deal found 1/20$169
This JetBlue deal was found by Cheapflights users on 1/21. 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.
Wed 3/1210:00 amMCO - ORH
Nonstop2h 52mJetBlue
Mon 3/171:47 pmORH - MCO
Nonstop3h 14mJetBlue
Deal found 1/21$183
This JetBlue deal was found by Cheapflights users on 1/19. 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.
Thu 2/207:45 amMCO - BDL
Nonstop2h 49mJetBlue
Wed 2/268:50 pmBDL - MCO
Nonstop3h 09mJetBlue
Deal found 1/19$187
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/188:00 amMCO - ALB
1 stop6h 03mDelta
Sun 2/236:35 pmALB - MCO
1 stop5h 01mDelta
Deal found 1/21$197

Find flights from Kissimmee to Massachusetts within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 2/7

5:30 am-8:18 am

Nonstop2h 48m

Hartford Bradley Intl

Sun 2/9

10:45 am-1:59 pm

Nonstop3h 14m

$68

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 1/31

6:24 pm-10:30 pm

1 stop4h 06m

Hartford Bradley Intl

Sun 2/2

10:45 am-1:59 pm

Nonstop3h 14m

$74

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 2/4

9:13 pm-12:13 am

Nonstop3h 00m

Boston Logan Intl

Tue 2/11

6:25 am-9:57 am

Nonstop3h 32m

$76

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Fri 1/31

9:23 pm-12:27 am

Nonstop3h 04m

Boston Logan Intl

Tue 2/4

6:00 am-9:34 am

Nonstop3h 34m

$77

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

Tue 1/28

9:23 pm-12:27 am

Nonstop3h 04m

Boston Logan Intl

Tue 2/4

10:00 am-1:29 pm

Nonstop3h 29m

$78

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 4/4

6:53 pm-10:59 pm

1 stop4h 06m

Hartford Bradley Intl

Sun 4/6

2:00 pm-6:19 pm

1 stop4h 19m

$102

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

Fri 2/7

6:09 am-5:05 pm

1 stop10h 56m

Hartford Bradley Intl

Sun 2/9

6:00 pm-8:07 am

1 stop14h 07m

$112

OrlandoAlbany

MCO - ALB

MCOALB

Orlando

Tue 2/18

8:59 pm-11:49 pm

Nonstop2h 50m

Albany Intl

Tue 2/25

6:00 am-9:17 am

Nonstop3h 17m

$157

OrlandoAlbany

MCO - ALB

MCOALB

Orlando

Fri 2/14

7:35 pm-12:13 am

1 stop4h 38m

Albany Intl

Mon 2/24

5:18 pm-12:31 am

1 stop7h 13m

$169

OrlandoWorcester

MCO - ORH

MCOORH

Orlando

Wed 3/12

10:00 am-12:52 pm

Nonstop2h 52m

Worcester

Mon 3/17

1:47 pm-5:01 pm

Nonstop3h 14m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 54 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.

Travel insights for flights from Kissimmee to Massachusetts

Get recent, data-driven insights about flights from Kissimmee to Massachusetts including ideal travel times, pricing trends, and more.

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 January 21, 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 January 21, 2025.

The most flights from K1S to USMA are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 21, 2025.
See what other customers who have flown with Spirit Airlines, Frontier and Delta from Kissimmee to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Breeze Airways
8.1
Very good
143 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $52 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $57 and Breeze Airways from $61 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 Etihad Airways (96%), Korean Air (95%) or Japan Airlines (92%) 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 $1,513, our data shows the cheapest flight currently is $45. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $71 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.

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
Fort Lauderdale to LaGuardia flights
Fort Lauderdale to Newark flights
Orlando to Newark flights
Miami to LaGuardia flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to Newark flights
Orlando to John F Kennedy Intl flights
Orlando to LaGuardia flights
Miami to Denver flights
Orlando to Dallas/Fort Worth flights
Orlando to Las Vegas flights
Orlando to Denver flights
Tampa to LaGuardia flights
Tampa to John F Kennedy Intl flights
Tampa to Newark flights
Miami to Los Angeles flights
Fort Lauderdale to Las Vegas flights
Miami to Las Vegas flights
Orlando to O'Hare Intl flights
Miami to Atlanta flights
Orlando to Los Angeles flights
Tampa to Las Vegas flights
Orlando to Dulles Intl flights
Miami to Reagan-National flights
Tampa to Denver flights
Fort Lauderdale to Boston flights
Orlando to Philadelphia flights
West Palm Beach to John F Kennedy Intl flights
Orlando to Seattle flights
Fort Lauderdale to Denver flights
Orlando to Hobby flights
Fort Lauderdale to Atlanta flights
Orlando to Boston flights
West Palm Beach to Atlanta flights
Fort Lauderdale to Los Angeles flights
Tampa to Seattle flights
West Palm Beach to LaGuardia flights
Tampa to Dulles Intl flights
Fort Lauderdale to Dallas/Fort Worth flights
Orlando to Baltimore flights
Miami to Boston flights
Miami to Dulles Intl flights
Orlando to Reagan-National flights
Orlando to Atlanta flights
Tampa to Atlanta flights
Fort Lauderdale to O'Hare Intl flights
Miami to Dallas/Fort Worth flights
Tampa to O'Hare Intl flights
Fort Lauderdale to New Orleans flights

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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$123FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$53Average$155FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$75Average$178FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$102Average$430FlexibilityNo cancel feeOn-time62%
DeltaCheapest$106Average$273FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$115Average$166FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$172Average$366FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$396FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$216Average$376FlexibilityNo cancel feeOn-time63%
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.