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$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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
may. 6 — may. 131
mar. 5/6
mar. 5/13
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 mayo 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$74
(eDestinos)

One-way from

$48
(Cheapflightsfares)

Popular in

April

Cheapest in

January

Average price

$139
Provider with most accurate pricing for Orlando (ORL)-Boston Logan Intl flight deals.
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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. 5% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in May 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 mayo 1, 2025.

This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/164:15 pmMCO - BDL
Nonstop2h 59mFrontier
lun. 5/198:14 pmBDL - MCO
Nonstop2h 58mFrontier
Deal found 4/29$74
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/29:25 pmMCO - BDL
Nonstop2h 50mSpirit Airlines
dom. 5/45:45 amBDL - MCO
Nonstop2h 50mSpirit Airlines
Deal found 4/29$76
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
sáb. 5/38:30 amMCO - BDL
Nonstop2h 56mMultiple Airlines
mar. 5/65:45 amBDL - MCO
Nonstop2h 50mMultiple Airlines
Deal found 4/29$80
This FlightHub deal was found by Cheapflights users on 4/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/218:17 amMCO - BOS
1 stop6h 27mSpirit Airlines
mar. 5/275:42 pmBOS - MCO
Nonstop3h 11mSpirit Airlines
Deal found 4/30$85
This CheapOair deal was found by Cheapflights users on 4/29. 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.
mar. 6/39:36 pmMCO - BDL
Nonstop2h 49mBreeze Airways
mar. 6/106:00 amBDL - MCO
Nonstop2h 54mBreeze Airways
Deal found 4/29$99
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
mié. 6/46:42 pmMCO - BOS
Nonstop3h 08mMultiple Airlines
vie. 6/139:40 amBOS - MCO
Nonstop3h 16mMultiple Airlines
Deal found 4/29$101
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
vie. 5/305:30 amMCO - BOS
Nonstop3h 10mFrontier
lun. 6/29:40 amBOS - MCO
Nonstop3h 16mFrontier
Deal found 4/30$106
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/237:00 pmMCO - BDL
Nonstop2h 55mJetBlue
mar. 5/275:44 pmBDL - MCO
Nonstop3h 01mJetBlue
Deal found 4/28$127
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 6/32:40 pmMCO - BDL
Nonstop2h 40mSouthwest
mar. 6/106:00 amBDL - MCO
1 stop4h 40mSouthwest
Deal found 4/29$137
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/275:18 pmMCO - BDL
1 stop7h 34mAmerican Airlines
mar. 6/34:22 pmBDL - MCO
1 stop5h 36mAmerican Airlines
Deal found 4/29$159
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/121:52 pmMCO - ALB
Nonstop2h 57mJetBlue
dom. 6/155:44 pmALB - MCO
Nonstop3h 05mJetBlue
Deal found 4/30$167
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/2911:50 amMCO - ORH
Nonstop2h 52mJetBlue
jue. 6/53:37 pmORH - MCO
Nonstop3h 10mJetBlue
Deal found 4/30$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 mayo 1, 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. 5/16

4:15 pm-7:14 pm

Nonstop2h 59m

Hartford Bradley Intl

lun. 5/19

8:14 pm-11:12 pm

Nonstop2h 58m

$74

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

sáb. 5/31

4:32 pm-7:31 pm

Nonstop2h 59m

Hartford Bradley Intl

lun. 6/2

1:52 pm-6:07 pm

1 stop4h 15m

$84

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

mié. 5/21

8:17 am-2:44 pm

1 stop6h 27m

Boston Logan Intl

mar. 5/27

5:42 pm-8:53 pm

Nonstop3h 11m

$85

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

sáb. 5/31

9:36 pm-12:25 am

Nonstop2h 49m

Hartford Bradley Intl

lun. 6/2

1:52 pm-6:07 pm

1 stop4h 15m

$97

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

mié. 6/4

6:42 pm-9:50 pm

Nonstop3h 08m

Boston Logan Intl

vie. 6/13

9:40 am-12:56 pm

Nonstop3h 16m

$101

OrlandoBoston

MCO - BOS

MCOBOS

Orlando

vie. 5/30

5:30 am-8:40 am

Nonstop3h 10m

Boston Logan Intl

lun. 6/2

9:40 am-12:56 pm

Nonstop3h 16m

$106

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

vie. 5/23

7:00 pm-9:55 pm

Nonstop2h 55m

Hartford Bradley Intl

mar. 5/27

5:44 pm-8:45 pm

Nonstop3h 01m

$127

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

mar. 6/3

2:40 pm-5:20 pm

Nonstop2h 40m

Hartford Bradley Intl

mar. 6/10

6:00 am-10:40 am

1 stop4h 40m

$137

OrlandoHartford

MCO - BDL

MCOBDL

Orlando

mar. 5/27

5:18 pm-12:52 am

1 stop7h 34m

Hartford Bradley Intl

mar. 6/3

4:22 pm-9:58 pm

1 stop5h 36m

$159

OrlandoAlbany

MCO - ALB

MCOALB

Orlando

jue. 6/12

1:52 pm-4:49 pm

Nonstop2h 57m

Albany Intl

dom. 6/15

5:44 pm-8:49 pm

Nonstop3h 05m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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, 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 $310). 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 mayo 1, 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 mayo 1, 2025.

The most flights from K1S to USMA are scheduled on a Thursday (63 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (16 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 mayo 1, 2025.
See what other customers who have flown with Breeze Airways, Alaska Airlines and Southwest 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.
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

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
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

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!
Alaska Airlines
8.0
Very good
9,972 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

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
4,294 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

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
7,934 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

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
8,696 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Crew

8.8

Overall

8.1

Food

6.7

Entertainment

6.6

Comfort

8.2

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 $48 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $49 and Breeze Airways from $50 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 (93%), Japan Airlines (91%) or Air France (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 $961, our data shows the cheapest flight currently is $51. When looking at the most popular route, (Orlando - Boston Logan Intl), you can expect to pay $79 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 $310). 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$117FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$40Average$147FlexibilityNo cancel feeOn-time65%
Breeze AirwaysCheapest$53Average$186FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$92Average$146FlexibilityNo cancel feeOn-time88%
DeltaCheapest$106Average$303FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$107Average$419FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$186Average$383FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$396FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$206Average$376FlexibilityNo cancel feeOn-time63%

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