$91 Find Cheap Flights from Boston to Kissimmee

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Kissimmee departing on 7/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights from Boston to Kissimmee

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$142
Typical prices: $337-$185
Frontier
Mon 5/18Tue 5/19
BOS - MCO • Non-stop
Cheapest one-way
$91
Typical prices: $98-$198
Frontier
Sat 7/4
BOS - MCO • 1 stop
Arrival airport
You can't fly directly to Kissimmee. It is served by Orlando (MCO), located 11 miles from Kissimmee.
FAQs
FAQs
FAQs
FAQs
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Kissimmee!
Flight Deals
Useful Info
Flight Deals

Cheap Flights from Boston to Kissimmee (BOS-MCO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Kissimmee that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Kissimmee

Mon, May 18 - Tue, May 19
Frontier Logo
10:17 am - 1:40 pm
BOS
-
MCO
3h 23mnonstop
Frontier Logo
6:00 am - 9:12 am
MCO
-
BOS
3h 12mnonstop
$142Frontier
Tue, May 19 - Wed, May 20
Frontier Logo
10:07 am - 1:30 pm
BOS
-
MCO
3h 23mnonstop
Frontier Logo
6:00 am - 9:12 am
MCO
-
BOS
3h 12mnonstop
$143Frontier
Mon, May 18 - Tue, May 19
Frontier Logo
10:17 am - 1:40 pm
BOS
-
MCO
3h 23mnonstop
Frontier Logo
6:00 am - 9:12 am
MCO
-
BOS
3h 12mnonstop
$144Frontier
Mon, May 18 - Fri, May 29
Spirit Airlines Logo
7:00 am - 10:10 am
BOS
-
MCO
3h 10mnonstop
Spirit Airlines Logo
6:36 pm - 9:42 pm
MCO
-
BOS
3h 06mnonstop
$145Spirit Airlines
Tue, Jun 2 - Wed, Jun 10
Multiple Airlines Logo
9:20 am - 12:29 pm
BOS
-
MCO
3h 09mnonstop
Multiple Airlines Logo
7:53 am - 1:27 am
MCO
-
BOS
17h 34m
1 stop
$146Multiple Airlines
Mon, May 18 - Wed, May 20
Frontier Logo
10:17 am - 1:40 pm
BOS
-
MCO
3h 23mnonstop
Frontier Logo
6:00 am - 9:12 am
MCO
-
BOS
3h 12mnonstop
$149Frontier
Tue, Jul 7 - Thu, Jul 9
Frontier Logo
11:05 am - 2:39 pm
BOS
-
MCO
3h 34mnonstop
Frontier Logo
7:00 am - 10:09 am
MCO
-
BOS
3h 09mnonstop
$152Frontier
Wed, Jul 8 - Mon, Jul 13
Frontier Logo
11:05 am - 2:39 pm
BOS
-
MCO
3h 34mnonstop
Frontier Logo
7:00 am - 10:09 am
MCO
-
BOS
3h 09mnonstop
$153Frontier
Tue, May 19 - Tue, May 19
Multiple Airlines Logo
9:20 am - 12:29 pm
BOS
-
MCO
3h 09mnonstop
Multiple Airlines Logo
5:10 pm - 1:24 am
MCO
-
BOS
8h 14m
1 stop
$154Multiple Airlines
Tue, May 26 - Fri, May 29
Multiple Airlines Logo
9:12 am - 9:47 pm
BOS
-
MCO
12h 35m
1 stop
Multiple Airlines Logo
6:36 pm - 9:42 pm
MCO
-
BOS
3h 06mnonstop
$155Multiple Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$91
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Boston to Orlando Airport

When to book flights from Boston to Kissimmee

Are your dates flexible? Find out the best times to travel from Boston to Kissimmee based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Boston to Kissimmee

  • Which airports will I be using when flying from Boston to Kissimmee?

    When flying out of Boston you’ll be using Boston Logan Intl. Kissimmee does not have its own airport so you’ll be flying into nearby Orlando airport, which is 11.0 mi away.

  • How long does a flight from Boston to Kissimmee take?

    Direct flights cover the 1,121 miles separating Boston and Kissimmee in about 3h 05m.

  • How many flights are there between Boston and Kissimmee?

    52 direct flights run between Boston and Kissimmee on a daily basis. On average, there are about 366 departures each week.

  • What’s the cheapest day of the week to fly between Boston and Kissimmee?

    Consider leaving on a Friday and avoid Saturdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Fridays and the most expensive ones on Mondays.

  • How does KAYAK find such low prices on flights from Boston to Kissimmee?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Kissimmee.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Kissimmee?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kissimmee from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Kissimmee?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kissimmee with an airline and back to Boston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Kissimmee?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kissimmee from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Boston to Kissimmee?

    In the last 72 hours, the cheapest one-way ticket between Boston and Kissimmee found on KAYAK was with Allegiant Air for $38. Breeze Airways offered a round-trip connection from $54 and Frontier from $61.

Top tips for finding cheap flights from Boston to Kissimmee

  • There is no airport in Kissimmee. Instead, you’ll be flying into Orlando Airport when flying between Boston and Kissimmee.
  • The cheapest flight from Boston to Kissimmee was found 24 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be March, April and May. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Boston to Kissimmee

 
Need help choosing which airline to fly with from Boston to Kissimmee? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8458 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
Airline reviews

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

4.0 OkayLifia, Apr 2026
BOS - SEA
Read more Delta reviews

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

N Everything was perfect from boarding to assistance to baggage in Tampa

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

The company went out of business and now I'm stuck in Ft. Lauderdale. Would not recommend.

Spirit changed flight times by 12 hours with coming and going so I refunded tickets and drove

The agent cancel my flight without my consent. So the situation generate me a lot of troubles, specially because we were traveling with a baby

Wonderful! Very polite crew that was dedicated to excellent customer service

The flight was delayed for over an hour. No one at the gate said anything about the flight being delayed. I had to rely on my phone for updates. Absolutely no communication at the gate.

The boarding process was simple but the seats were very uncomfortable. The staff lady was also very hard to understand when she spoke over the intercom about procedures and updates. Other staff members seemed like they were just tired and didnt want to be on the plane. Im used to happy attendants and being able to understand what is said over the speakers.

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

We were surprised to be charged $99 for a personal item. And of course everything offered on the flight was an additional charge. Other than that the pilot flew and landed the plane well and the attendants and fellow passengers were nice enough.

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

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

Complete your trip to Kissimmee with a hotel stay or car rental