$122+ Cheap flights from Boston (BOS) to Kissimmee, FL
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
Oct 7 — Oct 141
Round-trip
1 adult, Economy
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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 February, booked 24 days in advance, depart on a Thursday or Tuesday and return on a Friday
Cheap flight deals from Boston to Kissimmee
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to KissimmeeExplore the most affordable flight options available from Boston to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
Explore the most affordable flight options available from Boston to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
This Frontier deal was found by Cheapflights users on 9/2. 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.
Sat 10/312:54 pm -
1 stop9h 05m
Sun 10/47:52 am -
Nonstop3h 06m
Deal found 9/2![Frontier logo]()
$216
This Frontier deal was found by Cheapflights users on 9/3. 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.
Sat 12/511:57 am -
Nonstop3h 44m
Sun 12/139:29 pm -
1 stop11h 11m
Deal found 9/3![Frontier logo]()
$217
This deal was found by Cheapflights users on 9/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:06 am -
Nonstop3h 29m
Sat 12/57:50 am -
Nonstop3h 12m
Deal found 9/5![Frontier logo]()
$218
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:29 pm -
1 stop6h 43m
Wed 11/116:00 am -
1 stop4h 51m
Deal found 9/6![United Airlines logo]()
$219
This Frontier deal was found by Cheapflights users on 9/3. 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.
Thu 12/311:57 am -
Nonstop3h 44m
Sun 12/67:50 am -
Nonstop3h 12m
Deal found 9/3![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Thu 10/158:00 am -
1 stop13h 33m
Sat 10/177:45 am -
Nonstop3h 17m
Deal found 9/3![Multiple Airlines logo]()
$221
This Booking.com deal was found by Cheapflights users on 9/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:36 am -
Nonstop3h 16m
Mon 10/57:45 am -
Nonstop3h 06m
Deal found 9/3![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 9/7. 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.
Sat 10/312:54 pm -
1 stop9h 05m
Sat 10/247:45 am -
Nonstop3h 17m
Deal found 9/7![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 9/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:26 am -
Nonstop3h 16m
Fri 10/97:45 am -
Nonstop3h 17m
Deal found 9/4![Frontier logo]()
$225
This Expedia deal was found by Cheapflights users on 9/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/611:57 am -
Nonstop3h 44m
Sat 12/129:29 pm -
1 stop11h 11m
Deal found 9/3![Frontier logo]()
$227
Best flights from Boston to KissimmeeDiscover carefully curated flight deals from Boston to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
Discover carefully curated flight deals from Boston to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
This Southwest deal was found by Cheapflights users on 9/3. 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.
Wed 11/410:35 am -
1 stop6h 25m
Thu 11/57:25 am -
1 stop9h 45m
Deal found 9/3![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 9/6. 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.
Wed 11/115:40 pm -
Nonstop3h 23m
Mon 11/168:52 am -
1 stop6h 26m
Deal found 9/6![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 9/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:45 am -
2 stops8h 27m
Sat 10/106:00 pm -
1 stop6h 54m
Deal found 9/2![United Airlines logo]()
$294
This JetBlue deal was found by Cheapflights users on 9/6. 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 11/257:15 pm -
Nonstop3h 25m
Tue 12/14:04 pm -
Nonstop3h 05m
Deal found 9/6![JetBlue logo]()
$312
This Delta deal was found by Cheapflights users on 9/6. 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.
Thu 11/56:00 am -
1 stop6h 44m
Sat 11/77:00 am -
Nonstop3h 10m
Deal found 9/6![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 9/5. 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.
Sun 10/188:35 pm -
Nonstop3h 15m
Wed 10/216:16 pm -
1 stop5h 43m
Deal found 9/5![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 9/5. 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.
Sat 12/53:05 pm -
1 stop5h 25m
Sat 12/128:10 am -
1 stop6h 10m
Deal found 9/5![Southwest logo]()
$331
This Delta deal was found by Cheapflights users on 9/5. 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.
Sat 10/311:00 pm -
1 stop8h 15m
Sun 11/87:59 pm -
Nonstop3h 08m
Deal found 9/5![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 9/6. 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.
Sun 10/188:35 pm -
Nonstop3h 15m
Thu 10/229:25 am -
1 stop5h 24m
Deal found 9/6![Delta logo]()
$341
This Delta deal was found by Cheapflights users on 9/4. 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.
Thu 10/86:20 am -
1 stop7h 09m
Wed 10/146:16 pm -
1 stop5h 43m
Deal found 9/4![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 9/5. 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.
Fri 10/236:00 am -
1 stop6h 44m
Mon 10/263:55 pm -
1 stop6h 29m
Deal found 9/5![Delta logo]()
$351
Last-minute flights from Boston to KissimmeeDiscover last-minute flight deals from Boston to Kissimmee. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Kissimmee. Data last updated September 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Tue 9/2912:52 pm -
1 stop9h 07m
Sat 10/37:35 am -
Nonstop3h 06m
Deal found 9/7![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 9/3. 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.
Thu 10/111:17 am -
Nonstop3h 16m
Sun 10/117:45 am -
Nonstop3h 17m
Deal found 9/3![Frontier logo]()
$218
This Booking.com deal was found by Cheapflights users on 9/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:36 am -
Nonstop3h 16m
Mon 10/57:45 am -
Nonstop3h 06m
Deal found 9/3![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 9/2. 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.
Sat 10/312:54 pm -
1 stop9h 05m
Sun 10/47:52 am -
Nonstop3h 06m
Deal found 9/2![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Sat 10/312:54 pm -
1 stop9h 05m
Sat 10/107:45 am -
Nonstop3h 17m
Deal found 9/2![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/7. 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.
Sat 10/312:54 pm -
1 stop9h 05m
Sat 10/247:45 am -
Nonstop3h 17m
Deal found 9/7![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 9/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:26 am -
Nonstop3h 16m
Fri 10/97:45 am -
Nonstop3h 17m
Deal found 9/4![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 9/2. 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.
Sat 10/311:26 am -
Nonstop3h 16m
Mon 10/57:45 am -
Nonstop3h 06m
Deal found 9/2![Frontier logo]()
$226
This Delta deal was found by Cheapflights users on 9/4. 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 10/610:00 am -
1 stop4h 56m
Sat 10/105:42 pm -
1 stop5h 26m
Deal found 9/4![Delta logo]()
$219
This Frontier deal was found by Cheapflights users on 9/4. 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.
Thu 10/1511:47 am -
Nonstop3h 23m
Sun 10/187:45 am -
Nonstop3h 17m
Deal found 9/4![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Thu 10/158:00 am -
1 stop13h 33m
Sat 10/177:45 am -
Nonstop3h 17m
Deal found 9/3![Multiple Airlines logo]()
$221
One-way flights from Boston to KissimmeeSearch for one-way flight options from Boston to Kissimmee. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
Search for one-way flight options from Boston to Kissimmee. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Sat 11/2111:06 am -
Nonstop3h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 9/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:06 am -
Nonstop3h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$123
This Priceline deal was found by Cheapflights users on 9/2. 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.
Mon 11/2311:06 am -
Nonstop3h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:52 pm -
1 stop9h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 9/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:57 pm -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$127
This Frontier deal was found by Cheapflights users on 9/7. 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.
Thu 11/1212:39 pm -
1 stop8h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$129
This CheapOair deal was found by Cheapflights users on 9/3. 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.
Tue 11/1712:15 pm -
1 stop9h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$130
This Expedia deal was found by Cheapflights users on 9/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:27 am -
1 stop10h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$131
This Super.com deal was found by Cheapflights users on 9/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:54 pm -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 9/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:54 pm -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$133
This Super.com deal was found by Cheapflights users on 9/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:54 pm -
1 stop9h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$134
Find flight deals from Boston to Kissimmee
Keep the following information in mind while searching for Boston to Kissimmee flight deals. Data was last updated September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $216 (Frontier) |
One-way from | $122 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $306 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Kissimmee 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 7,457,451 searches. Data last updated September 7, 2026.
Use the filters below to find and compare flights from Boston to Kissimmee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Sat 11/7
7:31 am-5:18 pm
1 stop9h 47m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Tue 10/6
7:13 pm-12:59 am
1 stop5h 46m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Thu 10/29
10:40 am-3:20 pm
1 stop4h 40m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$161
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Mon 11/9
5:20 am-12:10 pm
1 stop6h 50m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$166
Quickest round-trip
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Tue 9/29
7:05 am-10:18 am
Nonstop3h 13m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Wed 9/30
8:20 pm-11:35 pm
Nonstop3h 15m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Tue 9/29
10:50 am-6:00 pm
2 stops7h 10m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$171
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Tue 11/24
6:30 am-11:55 am
1 stop5h 25m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$176
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Thu 10/1
5:50 am-1:25 pm
2 stops7h 35m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
BostonOrlando
BOS Boston Logan Intl - MCO Orlando
BOSMCO
Boston Logan Intl
Sat 11/7
7:25 pm-10:45 pm
Nonstop3h 20m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$209
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from Boston to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Boston with our price prediction graph.
BOS-MCO
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 Boston to Kissimmee
BOS-K1S
BOS-MCO
What is the cheapest time of day to fly from BOS to K1S?
Find hourly flight availability from Boston to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 7, 2026.
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 34% on airfare.
How much does it cost to fly round-trip from Boston to Kissimmee?
Airfare is below average for this route at the moment.
Boston to Kissimmee flights typically cost between $237 and $367 in October.The cheapest round-trip price found within the last 5 days was $216 on Frontier (Oct 3-Oct 4).
What is the cheapest day to fly from Boston to Kissimmee?
Use this chart to determine the cheapest time to fly round-trip from Boston to Kissimmee. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Boston to Kissimmee flight should consider departing on Wednesday at noon 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
Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated September 7, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andAmerican Airlines 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.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
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Boston and Kissimmee flights
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Top 8 airlines flying from Boston to Kissimmee
Discover the top 8 airlines that operate flights from Boston to Kissimmee. 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 7,457,451 searches. Data last updated September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$239 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$66 | Average$216 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$75 | Average$284 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$303 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$368 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$186 | Average$338 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$192 | Average$383 | FlexibilityNo cancel fee | On-time71% |