$92+ Cheap flights from Boston (BOS) to Kissimmee, FL
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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
Jun 20 — Jun 271
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 July, booked 24 days in advance, depart on a Thursday or Wednesday 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 May 21, 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 May 21, 2026.
This deal was found by Cheapflights users on 5/17. 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.
Fri 10/91:00 pm
BOS
- MCO
1 stop4h 54m
Frontier
Mon 10/125:15 am
MCO
- BOS
Nonstop3h 05m
Frontier
Deal found 5/17![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Wed 6/38:44 am
BOS
- MCO
1 stop13h 06m
Frontier
Tue 6/93:46 pm
MCO
- BOS
1 stop19h 19m
Frontier
Deal found 5/17![Frontier logo]()
$155
This Super.com deal was found by Cheapflights users on 5/18. 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 7/2711:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Wed 7/297:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/18![Frontier logo]()
$157
This Frontier deal was found by Cheapflights users on 5/17. 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 7/1811:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Wed 7/297:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/17![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Thu 7/910:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Wed 7/296:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$159
This Super.com deal was found by Cheapflights users on 5/19. 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.
Fri 7/1711:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Tue 7/287:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/19![Frontier logo]()
$161
This CheapOair deal was found by Cheapflights users on 5/20. 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 7/2510:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Wed 7/296:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$163
This Expedia deal was found by Cheapflights users on 5/17. 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.
Wed 7/2212:04 pm
BOS
- MCO
1 stop6h 29m
Frontier
Tue 7/287:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/17![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 7/710:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Thu 7/96:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 5/19![Frontier logo]()
$171
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 May 21, 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 May 21, 2026.
This Delta deal was found by Cheapflights users on 5/17. 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 6/94:30 pm
BOS
- MCO
1 stop5h 19m
Delta
Tue 6/167:00 am
MCO
- BOS
Nonstop3h 07m
Delta
Deal found 5/17![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 6/197:50 pm
BOS
- MCO
1 stop4h 55m
Southwest
Tue 6/239:45 am
MCO
- BOS
2 stops8h 00m
Southwest
Deal found 5/16![Southwest logo]()
$317
This JetBlue deal was found by Cheapflights users on 5/19. 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.
Sat 6/208:31 pm
BOS
- MCO
Nonstop3h 11m
JetBlue
Tue 6/236:00 am
MCO
- BOS
Nonstop3h 04m
JetBlue
Deal found 5/19![JetBlue logo]()
$322
This Delta deal was found by Cheapflights users on 5/17. 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 5/313:30 pm
BOS
- MCO
Nonstop3h 24m
Delta
Wed 6/39:44 am
MCO
- BOS
1 stop5h 15m
Delta
Deal found 5/17![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 5/18. 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 6/231:00 pm
BOS
- MCO
1 stop6h 04m
Delta
Wed 6/247:00 am
MCO
- BOS
Nonstop3h 07m
Delta
Deal found 5/18![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 5/18. 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 8/265:25 am
BOS
- MCO
2 stops8h 50m
Southwest
Sat 8/298:00 am
MCO
- BOS
1 stop6h 10m
Southwest
Deal found 5/18![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 5/17. 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 8/118:55 am
BOS
- MCO
1 stop7h 45m
Delta
Wed 8/1911:29 am
MCO
- BOS
1 stop5h 44m
Delta
Deal found 5/17![Delta logo]()
$287
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 6/197:50 pm
BOS
- MCO
1 stop4h 55m
Southwest
Mon 6/225:20 pm
MCO
- BOS
1 stop6h 50m
Southwest
Deal found 5/16![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 5/20. 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 10/107:59 pm
BOS
- MCO
Nonstop3h 21m
Delta
Sat 10/177:00 am
MCO
- BOS
Nonstop3h 04m
Delta
Deal found 5/20![Delta logo]()
$317
This Delta deal was found by Cheapflights users on 5/17. 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 9/157:59 pm
BOS
- MCO
Nonstop3h 14m
Delta
Tue 9/297:00 am
MCO
- BOS
1 stop5h 24m
Delta
Deal found 5/17![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 5/16. 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 8/206:45 am
BOS
- MCO
1 stop5h 15m
Delta
Sun 8/237:00 am
MCO
- BOS
Nonstop3h 10m
Delta
Deal found 5/16![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 5/20. 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 6/231:00 pm
BOS
- MCO
1 stop6h 04m
Delta
Mon 6/293:36 pm
MCO
- BOS
1 stop7h 05m
Delta
Deal found 5/20![Delta logo]()
$328
Last-minute flights from Boston to KissimmeeDiscover last-minute flight deals from Boston to Kissimmee. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Kissimmee. Data last updated May 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Wed 6/38:44 am
BOS
- MCO
1 stop13h 06m
Frontier
Tue 6/93:46 pm
MCO
- BOS
1 stop19h 19m
Frontier
Deal found 5/17![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Wed 6/38:44 am
BOS
- MCO
1 stop13h 06m
Frontier
Tue 6/167:25 am
MCO
- BOS
1 stop27h 40m
Frontier
Deal found 5/17![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Wed 6/38:44 am
BOS
- MCO
1 stop13h 06m
Frontier
Wed 6/105:25 am
MCO
- BOS
1 stop20h 02m
Frontier
Deal found 5/18![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/68:40 am
BOS
- MCO
1 stop13h 10m
Frontier
Tue 6/93:46 pm
MCO
- BOS
1 stop19h 19m
Frontier
Deal found 5/19![Frontier logo]()
$191
This Expedia deal was found by Cheapflights users on 5/18. 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.
Wed 6/108:47 am
BOS
- MCO
1 stop7h 45m
Frontier
Wed 6/171:45 pm
MCO
- BOS
1 stop11h 42m
Frontier
Deal found 5/18![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Wed 6/108:47 am
BOS
- MCO
1 stop7h 45m
Frontier
Tue 6/163:46 pm
MCO
- BOS
1 stop19h 19m
Frontier
Deal found 5/17![Frontier logo]()
$197
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 May 21, 2026.
Search for one-way flight options from Boston to Kissimmee. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This Trip.com deal was found by Cheapflights users on 5/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:43 am
BOS
- MCO
1 stop7h 49m
Frontier
Deal found 5/17![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 5/19. 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.
Mon 8/3111:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Deal found 5/19![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 5/20. 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.
Fri 7/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 5/20![Frontier logo]()
$94
This CheapOair deal was found by Cheapflights users on 5/19. 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.
Wed 7/158:47 am
BOS
- MCO
1 stop7h 50m
Frontier
Deal found 5/19![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 7/1110:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 5/20![Frontier logo]()
$96
This Trip.com deal was found by Cheapflights users on 5/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:47 am
BOS
- MCO
1 stop10h 39m
Frontier
Deal found 5/19![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/166:00 am
BOS
- MCO
1 stop16h 09m
Frontier
Deal found 5/17![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Wed 10/71:00 pm
BOS
- MCO
1 stop9h 10m
Frontier
Deal found 5/20![Frontier logo]()
$100
This Frontier deal was found by Cheapflights users on 5/18. 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.
Wed 8/56:00 am
BOS
- MCO
1 stop12h 33m
Frontier
Deal found 5/18![Frontier logo]()
$101
This Trip.com deal was found by Cheapflights users on 5/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:40 am
BOS
- MCO
1 stop13h 24m
Frontier
Deal found 5/18![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 8/189:12 am
BOS
- MCO
1 stop24h 45m
Frontier
Deal found 5/20![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 9/19:12 am
BOS
- MCO
1 stop21h 33m
Frontier
Deal found 5/20![Frontier logo]()
$104
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 May 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $142 |
One-way from | $92 (Trip.com) |
Popular in | April |
Cheapest in | January |
Average price | $277 |
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 2,558,603 searches. Data last updated May 21, 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 - MCO
BOSMCO
Boston Logan Intl
Tue 6/9
4:30 pm-9:49 pm
1 stop5h 19m
Orlando
Tue 6/16
7:00 am-10:07 am
Nonstop3h 07m
$242
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sun 5/31
3:30 pm-6:54 pm
Nonstop3h 24m
Orlando
Wed 6/3
9:44 am-2:59 pm
1 stop5h 15m
$257
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Tue 6/23
1:00 pm-7:04 pm
1 stop6h 04m
Orlando
Wed 6/24
7:00 am-10:07 am
Nonstop3h 07m
$277
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Tue 8/11
8:55 am-4:40 pm
1 stop7h 45m
Orlando
Wed 8/19
11:29 am-5:13 pm
1 stop5h 44m
$287
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Fri 6/19
7:50 pm-12:45 am
1 stop4h 55m
Orlando
Tue 6/23
9:45 am-5:45 pm
2 stops8h 00m
$317
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Wed 8/26
5:25 am-2:15 pm
2 stops8h 50m
Orlando
Sat 8/29
8:00 am-2:10 pm
1 stop6h 10m
$317
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 10/10
7:59 pm-11:20 pm
Nonstop3h 21m
Orlando
Sat 10/17
7:00 am-10:04 am
Nonstop3h 04m
$317
Quickest round-trip
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 6/20
8:31 pm-11:42 pm
Nonstop3h 11m
Orlando
Tue 6/23
6:00 am-9:04 am
Nonstop3h 04m
$322
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Tue 9/15
7:59 pm-11:13 pm
Nonstop3h 14m
Orlando
Tue 9/29
7:00 am-12:24 pm
1 stop5h 24m
$327
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Thu 8/20
6:45 am-12:00 pm
1 stop5h 15m
Orlando
Sun 8/23
7:00 am-10:10 am
Nonstop3h 10m
$327
Showing 1-10 of 24 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 May 21, 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 afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 4% on airfare.
Weekly flight availability from Boston to Kissimmee
Explore weekly flight availability from Boston to Kissimmee. 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 May 21, 2026.
The most flights from BOS to K1S are scheduled on a Thursday (42 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Boston to Kissimmee?
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 May 16, 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 afternoons 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 May 21, 2026.
Peruse reviews from past customers who have flown with Delta,JetBlue, 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.
Overall
7.9
Comfort
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Comfort
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Comfort
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Comfort
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Spirit Airlines
Overall
7.9
Comfort
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Overall
7.9
Comfort
7.8
Entertainment
7.8
Crew
8.5
Food
7.2
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Related info for your journey
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Boston and Kissimmee flights
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Top 9 airlines flying from Boston to Kissimmee
Discover the top 9 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 2,558,603 searches. Data last updated May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$218 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$62 | Average$174 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$206 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$75 | Average$300 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$302 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$122 | Average$351 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$336 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$178 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$339 | FlexibilityNo cancel fee | On-time69% |