$103 Find Cheap Flights from Boston to Kissimmee - Compare and Save

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 9/12. 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.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$189
Typical prices: $200-$351
Frontier
Sat 9/5Sun 9/6
BOS - MCO • Non-stop
Cheapest one-way
$102
Typical prices: $109-$201
Frontier
Sat 9/12
BOS - MCO • Non-stop
Arrival airport
You can't fly directly to Kissimmee. It is served by Orlando (MCO), located 11 miles from Kissimmee.
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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

Sat, Sep 5 - Sun, Sep 6
Frontier Logo
10:04 am - 1:40 pmBOS  Boston Logan Intl-MCO Orlando
3h 36mnonstop
Frontier Logo
6:00 am - 9:09 amMCO  Orlando-BOS Boston Logan Intl
3h 09mnonstop
$189Frontier
Sat, Sep 5 - Fri, Sep 11
Frontier Logo
10:04 am - 1:40 pmBOS  Boston Logan Intl-MCO Orlando
3h 36mnonstop
Frontier Logo
7:45 am - 10:51 amMCO  Orlando-BOS Boston Logan Intl
3h 06mnonstop
$189Frontier
Sat, Sep 5 - Fri, Sep 11
Multiple Airlines Logo
10:04 am - 1:40 pmBOS  Boston Logan Intl-MCO Orlando
3h 36mnonstop
Multiple Airlines Logo
10:53 am - 11:45 amMCO  Orlando-BOS Boston Logan Intl
24h 52m1 stop Knoxville McGhee Tyson
$191Multiple Airlines
Mon, Oct 26 - Thu, Nov 5
Multiple Airlines Logo
9:15 am - 12:37 pmBOS  Boston Logan Intl-MCO Orlando
3h 22mnonstop
Multiple Airlines Logo
7:10 am - 9:29 amMCO  Orlando-BOS Boston Logan Intl
50h 19m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$192Multiple Airlines
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
11:20 am - 4:00 pmBOS  Boston Logan Intl-MCO Orlando
4h 40m1 stop Baltimore/Washington
Southwest Logo
7:20 am - 3:25 pmMCO  Orlando-BOS Boston Logan Intl
8h 05m1 stop Austin Bergstrom
$202Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
10:40 am - 3:20 pmBOS  Boston Logan Intl-MCO Orlando
4h 40m1 stop Baltimore/Washington
Southwest Logo
8:10 am - 2:25 pmMCO  Orlando-BOS Boston Logan Intl
6h 15m1 stop Chicago Midway
$202Southwest
Sat, Sep 19 - Tue, Sep 22
JetBlue Logo
8:15 pm - 11:32 pmBOS  Boston Logan Intl-MCO Orlando
3h 17mnonstop
JetBlue Logo
5:00 pm - 8:41 pmMCO  Orlando-BOS Boston Logan Intl
3h 41mnonstop
$207JetBlue
Wed, Sep 16 - Tue, Sep 22
JetBlue Logo
8:15 pm - 11:32 pmBOS  Boston Logan Intl-MCO Orlando
3h 17mnonstop
JetBlue Logo
7:00 am - 9:59 amMCO  Orlando-BOS Boston Logan Intl
2h 59mnonstop
$207JetBlue
Wed, Sep 30 - Tue, Oct 6
Delta Logo
8:20 pm - 11:35 pmBOS  Boston Logan Intl-MCO Orlando
3h 15mnonstop
Delta Logo
3:40 pm - 6:49 pmMCO  Orlando-BOS Boston Logan Intl
3h 09mnonstop
$209Delta
Sat, Sep 26 - Tue, Oct 6
Delta Logo
7:35 pm - 10:50 pmBOS  Boston Logan Intl-MCO Orlando
3h 15mnonstop
Delta Logo
7:00 am - 10:10 amMCO  Orlando-BOS Boston Logan Intl
3h 10mnonstop
$209Delta
Useful Info

Good to know

Low season

June

Cheapest flight

$103
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 22% 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 06m.

  • How many flights are there between Boston and Kissimmee?

    54 direct flights run between Boston and Kissimmee on a daily basis. On average, there are about 380 departures each week.

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

    Consider leaving on a Thursday and avoid Saturdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Thursdays 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 5 days, the cheapest one-way ticket between Boston and Kissimmee found on KAYAK was with Frontier for $41. Breeze Airways offered a round-trip connection from $61 and Frontier from $67.

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 23 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.
8.0
SouthwestOverall score based on 4216 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

6.0 GoodGordon, Jul 2026
Read more Southwest reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

WiFi was not working and didn’t have a beverage service

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Stewardess was not accommodating when I requested a second drink.

Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

It is usually very pleasant. Good service for the price, international flights are even better

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

They did a fine job. Can't wait to use Delta in the future.

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

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.

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.

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

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

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

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

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

ticketing issues caused many customers to have to go back to check in after waiting in security, then go through security line again.

Our flight was delayed 2 hours and when they changed the the time to 1 hour I wasn't alerted and when I checked the gate the plane was still there but they already shut the doors so I had to buy another flight.

The flight was great . But you only had one vegan item on the whole flight and someone prior to me took it . I was so disappointed cause I came in from the flooded area and couldn’t pick up anything prior to my flight .

Plane was hot and miserable and the crew was rude!

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

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Better than expected. Staff were friendly and nice on both flights.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

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

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