$98+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
Jul 13 — Jul 201
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 22 days in advance, depart on a Thursday or Friday and return on a Friday
Cheap flight deals from Boston to Kissimmee
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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 June 13, 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 June 13, 2026.
This Orbitz deal was found by Cheapflights users on 6/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Sun 9/207:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 9/1411:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Mon 9/217:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$142
This Expedia deal was found by Cheapflights users on 6/12. 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.
Thu 9/311:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Thu 9/107:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$144
This Frontier deal was found by Cheapflights users on 6/11. 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.
Sun 8/3011:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Sun 9/67:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/11![Frontier logo]()
$146
This Super.com deal was found by Cheapflights users on 6/9. 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 7/1710:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Mon 7/206:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/9![Frontier logo]()
$148
This Super.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/3010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Sun 8/26:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/11![Frontier logo]()
$149
This Frontier deal was found by Cheapflights users on 6/10. 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.
Fri 7/2410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Sun 8/26:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 6/10. 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.
Mon 7/2010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$153
This Frontier deal was found by Cheapflights users on 6/10. 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.
Fri 7/2410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$154
This Booking.com deal was found by Cheapflights users on 6/12. 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 7/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Mon 7/136:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$155
This Super.com deal was found by Cheapflights users on 6/12. 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 7/810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Tue 7/216:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$156
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 June 13, 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 June 13, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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 8/192:45 pm
BOS
- MCO
1 stop6h 20m
Southwest
Wed 8/268:30 am
MCO
- BOS
1 stop6h 10m
Southwest
Deal found 6/11![Southwest logo]()
$183
This Delta deal was found by Cheapflights users on 6/10. 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 9/158:20 pm
BOS
- MCO
Nonstop3h 15m
Delta
Tue 9/297:05 am
MCO
- BOS
Nonstop3h 10m
Delta
Deal found 6/10![Delta logo]()
$197
This JetBlue deal was found by Cheapflights users on 6/9. 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 7/114:43 pm
BOS
- MCO
1 stop7h 25m
JetBlue
Sat 7/186:00 am
MCO
- BOS
1 stop8h 24m
JetBlue
Deal found 6/9![JetBlue logo]()
$229
This Delta deal was found by Cheapflights users on 6/12. 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 9/128:30 am
BOS
- MCO
1 stop6h 05m
Delta
Sat 9/197:05 am
MCO
- BOS
Nonstop3h 10m
Delta
Deal found 6/12![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 6/11. 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 9/239:20 am
BOS
- MCO
1 stop5h 07m
Delta
Sat 9/267:05 am
MCO
- BOS
Nonstop3h 10m
Delta
Deal found 6/11![Delta logo]()
$207
This JetBlue deal was found by Cheapflights users on 6/8. 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.
Sun 8/168:15 pm
BOS
- MCO
Nonstop3h 13m
JetBlue
Tue 8/186:00 am
MCO
- BOS
1 stop8h 41m
JetBlue
Deal found 6/8![JetBlue logo]()
$248
This Delta deal was found by Cheapflights users on 6/8. 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 8/264:00 pm
BOS
- MCO
1 stop7h 03m
Delta
Wed 9/27:59 pm
MCO
- BOS
Nonstop3h 21m
Delta
Deal found 6/8![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 6/10. 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 8/227:35 pm
BOS
- MCO
Nonstop3h 19m
Delta
Wed 8/266:15 am
MCO
- BOS
1 stop6h 30m
Delta
Deal found 6/10![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 10/209:00 am
BOS
- MCO
2 stops7h 10m
Southwest
Sun 10/259:05 am
MCO
- BOS
2 stops6h 50m
Southwest
Deal found 6/9![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/215:35 am
BOS
- MCO
2 stops8h 30m
Southwest
Tue 7/286:35 pm
MCO
- BOS
1 stop4h 50m
Southwest
Deal found 6/12![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 6/8. 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 8/187:55 am
BOS
- MCO
1 stop7h 43m
Delta
Tue 8/187:55 pm
MCO
- BOS
1 stop5h 30m
Delta
Deal found 6/8![Delta logo]()
$287
Last-minute flights from Boston to KissimmeeDiscover last-minute flight deals from Boston to Kissimmee. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Kissimmee. Data last updated June 13, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 6/12. 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 7/810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Tue 7/216:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$156
This Super.com deal was found by Cheapflights users on 6/11. 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 7/810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Wed 7/226:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/11![Frontier logo]()
$157
This Booking.com deal was found by Cheapflights users on 6/12. 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 7/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Mon 7/136:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$155
This Super.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/1610:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Wed 7/226:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/12![Frontier logo]()
$160
This Super.com deal was found by Cheapflights users on 6/9. 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 7/1710:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Mon 7/206:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/9![Frontier logo]()
$148
This Orbitz deal was found by Cheapflights users on 6/10. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Wed 7/226:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$158
This Frontier deal was found by Cheapflights users on 6/10. 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.
Mon 7/2010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$153
This Booking.com deal was found by Cheapflights users on 6/13. 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.
Mon 7/2010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Wed 7/226:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/13![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 6/10. 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.
Fri 7/2410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Sun 8/26:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$150
This Frontier deal was found by Cheapflights users on 6/10. 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.
Fri 7/2410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/10![Frontier logo]()
$154
This Super.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/3010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Sun 8/26:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/11![Frontier logo]()
$149
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 June 13, 2026.
Search for one-way flight options from Boston to Kissimmee. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This Trip.com deal was found by Cheapflights users on 6/12. 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.
Fri 9/1811:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Deal found 6/12![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 6/13. 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 7/810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/13![Frontier logo]()
$99
This Trip.com deal was found by Cheapflights users on 6/10. 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 6/10![Frontier logo]()
$100
This Trip.com deal was found by Cheapflights users on 6/9. 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 9/58:40 am
BOS
- MCO
1 stop13h 24m
Frontier
Deal found 6/9![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 6/12![Frontier logo]()
$103
This Expedia deal was found by Cheapflights users on 6/9. 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.
Mon 10/129:15 am
BOS
- MCO
Nonstop3h 22m
Frontier
Deal found 6/9![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 6/10. 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 8/128:41 am
BOS
- MCO
1 stop7h 51m
Frontier
Deal found 6/10![Frontier logo]()
$105
This Southwest deal was found by Cheapflights users on 6/9. 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 10/710:45 am
BOS
- MCO
1 stop5h 50m
Southwest
Deal found 6/9![Southwest logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 8/248:47 am
BOS
- MCO
1 stop13h 17m
Frontier
Deal found 6/9![Frontier logo]()
$107
This Southwest deal was found by Cheapflights users on 6/9. 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 8/295:50 am
BOS
- MCO
1 stop5h 40m
Southwest
Deal found 6/9![Southwest logo]()
$108
This United Airlines deal was found by Cheapflights users on 6/9. 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 9/267:13 pm
BOS
- MCO
1 stop5h 46m
United Airlines
Deal found 6/9![United Airlines logo]()
$109
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 June 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $138 (Orbitz) |
One-way from | $98 (Trip.com) |
Popular in | April |
Cheapest in | January |
Average price | $342 |
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 June 13, 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
Wed 8/19
2:45 pm-9:05 pm
1 stop6h 20m
Orlando
Wed 8/26
8:30 am-2:40 pm
1 stop6h 10m
$183
Quickest round-trip
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Tue 9/15
8:20 pm-11:35 pm
Nonstop3h 15m
Orlando
Tue 9/29
7:05 am-10:15 am
Nonstop3h 10m
$197
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 9/12
8:30 am-2:35 pm
1 stop6h 05m
Orlando
Sat 9/19
7:05 am-10:15 am
Nonstop3h 10m
$207
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Wed 9/23
9:20 am-2:27 pm
1 stop5h 07m
Orlando
Sat 9/26
7:05 am-10:15 am
Nonstop3h 10m
$207
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Wed 8/26
4:00 pm-11:03 pm
1 stop7h 03m
Orlando
Wed 9/2
7:59 pm-11:20 pm
Nonstop3h 21m
$207
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 8/22
7:35 pm-10:54 pm
Nonstop3h 19m
Orlando
Wed 8/26
6:15 am-12:45 pm
1 stop6h 30m
$207
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 7/11
4:43 pm-12:08 am
1 stop7h 25m
Orlando
Sat 7/18
6:00 am-2:24 pm
1 stop8h 24m
$229
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sun 8/16
8:15 pm-11:28 pm
Nonstop3h 13m
Orlando
Tue 8/18
6:00 am-2:41 pm
1 stop8h 41m
$248
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Tue 8/18
7:55 am-3:38 pm
1 stop7h 43m
Orlando
Tue 8/18
7:55 pm-1:25 am
1 stop5h 30m
$287
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Tue 10/20
9:00 am-4:10 pm
2 stops7h 10m
Orlando
Sun 10/25
9:05 am-3:55 pm
2 stops6h 50m
$295
Showing 1-10 of 23 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 June 13, 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 7% 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 June 13, 2026.
The most flights from BOS to K1S are scheduled on a Thursday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 June 13, 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 June 13, 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.
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Boston to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Boston to Kissimmee
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Kissimmee by cabin class
Find flights from Boston to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Kissimmee flights
Browse other Boston and Kissimmee flight options. Last updated on June 13, 2026.
Other flights from Boston
Browse through other flights departing from Boston. Flights are based on user searches made on Cheapflights and were last updated on June 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Kissimmee flights
Consider these flights traveling from Boston to Kissimmee.
Top 8 airlines flying from Boston to Kissimmee
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 2,558,603 searches. Data last updated June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$226 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$62 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$75 | Average$236 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$88 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$122 | Average$355 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$336 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$178 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$186 | Average$337 | FlexibilityNo cancel fee | On-time69% |