What are the cheapest airlines to fly from Boston to Kissimmee one-way?

The cheapest airlines for a one-way flight from Boston to Kissimmee are Frontier ($44), Breeze Airways ($56), and JetBlue ($79).

Weekly flight availability from Boston to Kissimmee

The most flights from BOS to K1S are scheduled on a Monday (53 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 on average).

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

If weather is an important factor for your trip to Kissimmee, 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 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

What are the cheapest flights from Boston to Kissimmee?

Looking at all options, your cheapest flight can be booked for $126. While the most popular route (Boston Logan Intl - Orlando) can be booked for $153 on average, our data indicates $619 when flying from Boston to Kissimmee.

What are the most reliable airlines from Boston to Kissimmee?

No one likes to see their flight delayed. When booking a flight from Boston to Kissimmee consider choosing American Airlines (94%), LATAM Airlines (77%) or Air France (77%) as they are the most reliable in getting you off to your destination on time.

What are the most popular airlines that fly from Boston to Kissimmee?

JetBlue, Delta and American Airlines are the most popular airlines when flying from Boston to Kissimmee.

What airport do you fly from for flights from Boston to Kissimmee?

If you book a flight to Kissimmee from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 41 flights from Logan Intl to Kissimmee per day from 8 different airlines.

Can I find deals for flights from Boston to Kissimmee that include hotel bookings?

Yes. In addition to deals on Boston to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Boston to Kissimmee?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Kissimmee.

Can I find deals for business class flights from Boston to Kissimmee?

Yes. Cheapflights offers flight deals from Boston to Kissimmee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Find Cheap Flights from Boston to Kissimmee

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Boston to Kissimmee 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.

Cheapflights Tip: The best prices from Boston Logan Intl to Kissimmee are usually found in January or May, booked 24 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Find flight deals from Boston to Kissimmee

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	November
Cheapest in	January
Average price	$350

Provider with most accurate pricing for Boston Logan Intl-Orlando (ORL) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Boston Logan Intl-Orlando (ORL) flights.

Search Deals

Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2026

Search Deals

Cheapflights Insights

Everything you need to know about your flight from Boston to Kissimmee

Prices

Airlines

What is the cheapest time of day to fly from BOS to K1S?

One of the essential ways to save on airfare from Boston to Kissimmee is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 33% on airfare.

What is the cheapest day to fly from Boston to Kissimmee?

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Kissimmee

Peruse reviews from past customers who have flown with Southwest,Delta, andJetBlue from Boston to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

7.9

Good

4,207 reviews

Reviews

1 / 20

8.0

Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Southwest

7.9

Good

4,207 reviews

Southwest

7.9

Good

4,207 reviews

Reviews

1 / 20

8.0

Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Delta

7.8

Good

8,654 reviews

Southwest

7.9

Good

4,207 reviews

Reviews

1 / 20

8.0

Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

JetBlue

7.1

Good

3,060 reviews

Southwest

7.9

Good

4,207 reviews

Reviews

1 / 20

8.0

Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

American Airlines

7.0

Good

12,179 reviews

Southwest

7.9

Good

4,207 reviews

Reviews

1 / 20

8.0

Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Frontier

5.5

Fair

2,521 reviews

Southwest

7.9

Good

4,207 reviews

Reviews

1 / 20

8.0

Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

What airport do you fly from for flights from Boston to Kissimmee?
If you book a flight to Kissimmee from Boston, you will be flying from Logan Intl, which is the city’s only airport. Boston Logan Intl (BOS) is located 2.6 mi from the center of Boston. There are 41 flights from Logan Intl to Kissimmee per day from 8 different airlines.
What are the cheapest airlines to fly from Boston to Kissimmee one-way?
The cheapest airlines for a one-way flight from Boston to Kissimmee are Frontier ($44), Breeze Airways ($56), and JetBlue ($79).
What are the most reliable airlines from Boston to Kissimmee?
No one likes to see their flight delayed. When booking a flight from Boston to Kissimmee consider choosing American Airlines (94%), LATAM Airlines (77%) or Air France (77%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Boston to Kissimmee?
Looking at all options, your cheapest flight can be booked for $126. While the most popular route (Boston Logan Intl - Orlando) can be booked for $153 on average, our data indicates $619 when flying from Boston to Kissimmee.
Can I find deals for flights from Boston to Kissimmee that include hotel bookings?
Yes. In addition to deals on Boston to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Boston to Kissimmee?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Kissimmee.
Can I find deals for business class flights from Boston to Kissimmee?
Yes. Cheapflights offers flight deals from Boston to Kissimmee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes

Complete your trip

Flights by cabin class

Other flight options

Other flights from Boston

Popular flights

Top destinations

Alternative routes for Boston to Kissimmee

Boston to Orlando flights

Boston to Miami flights

Boston to Fort Lauderdale flights

Hartford to Orlando flights

Boston to Tampa flights

Boston to Fort Myers flights

Hartford to Fort Lauderdale flights

Boston to Sarasota flights

Hartford to Tampa flights

Hartford to Miami flights

Albany to Orlando flights

Boston to Jacksonville flights

Boston to Key West flights

Hartford to Fort Myers flights

Albany to Fort Lauderdale flights

Boston to Orlando Sanford Intl flights

Boston to St Petersburg flights

Worcester to Orlando flights

Hartford to Sarasota flights

Albany to Tampa flights

Worcester to Fort Lauderdale flights

Albany to Miami flights

Boston to Daytona Beach flights

Hartford to Key West flights

Hartford to Jacksonville flights

Boston to Panama City flights

Boston to Valparaiso flights

Hartford to Daytona Beach flights

Boston to Pensacola flights

Albany to Sarasota flights

Albany to Fort Myers flights

Worcester to Fort Myers flights

Worcester to Tampa flights

Albany to Orlando Sanford Intl flights

Hartford to St Petersburg flights

Hartford to Melbourne flights

Hartford to Pensacola flights

Albany to Key West flights

Worcester to Miami flights

Boston to Melbourne flights

Albany to Daytona Beach flights

Boston to Gainesville flights

Albany to St Petersburg flights

Albany to Melbourne flights

Albany to Jacksonville flights

Hartford to Panama City flights

Albany to Pensacola flights

Top 8 airlines flying from Boston to Kissimmee

Airline	Cheapest	Average	Flexibility	On-time
Breeze Airways	Cheapest$61	Average$239	FlexibilityNo cancel fee	On-timeN/A
Frontier	Cheapest$74	Average$243	FlexibilityNo cancel fee	On-time62%
Allegiant Air	Cheapest$75	Average$286	FlexibilityNo cancel fee	On-time88%
JetBlue	Cheapest$88	Average$322	FlexibilityNo cancel fee	On-time62%
Delta	Cheapest$144	Average$383	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$156	Average$401	FlexibilityNo cancel fee	On-time63%
American Airlines	Cheapest$192	Average$374	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$197	Average$356	FlexibilityNo cancel fee	On-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.

Cheap flights from Boston (BOS) to Kissimmee, FL

Find cheap flights from Boston to Kissimmee with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Find flight deals from Boston to Kissimmee

Most accurate provider

Most trusted provider

Popular in

Cheapest in

Average price

Cheapflights Insights

What is the cheapest time of day to fly from BOS to K1S?

One of the essential ways to save on airfare from Boston to Kissimmee is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 33% on airfare.

What is the cheapest day to fly from Boston to Kissimmee?

Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Kissimmee

The most flights from BOS to K1S are scheduled on a Monday (53 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 on average).

Reviews of airlines servicing Kissimmee

Peruse reviews from past customers who have flown with Southwest,Delta, andJetBlue from Boston to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What airport do you fly from for flights from Boston to Kissimmee?

What are the cheapest airlines to fly from Boston to Kissimmee one-way?

What are the most reliable airlines from Boston to Kissimmee?

What are the cheapest flights from Boston to Kissimmee?

Can I find deals for flights from Boston to Kissimmee that include hotel bookings?

How can I find direct flights from Boston to Kissimmee?

Can I find deals for business class flights from Boston to Kissimmee?

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 Boston to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.

Complete your trip

Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Boston to Kissimmee by cabin class

Find flights from Boston to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Boston and Kissimmee flights

Browse other Boston and Kissimmee flight options. Last updated on October 21, 2026.

Other flights from Boston

Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on October 21, 2026.

Popular flight searches

Check out other popular destinations found by fellow travelers in 2026

Boston to Kissimmee flights

Consider these flights traveling from Boston to Kissimmee.

Top 8 airlines flying from Boston to Kissimmee

100% Free

Book with Flexibility

Travel Smart