$73+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MCO
May 1 — May 81
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 17 days in advance, depart on a Thursday or Wednesday and return on a Friday
Cheap flight deals from Boston to Kissimmee
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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 April 1, 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 April 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
Sun 4/59:45 am
BOS
- MCO
Nonstop3h 15m
Multiple Airlines
Sat 4/118:10 am
MCO
- BOS
Nonstop3h 09m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/1312:45 pm
BOS
- MCO
1 stop5h 58m
Frontier
Fri 4/177:05 am
MCO
- BOS
Nonstop3h 16m
Frontier
Deal found 3/27![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/117:14 pm
BOS
- MCO
Nonstop3h 17m
Multiple Airlines
Thu 4/167:00 am
MCO
- BOS
Nonstop3h 16m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$142
This Frontier deal was found by Cheapflights users on 3/30. 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 5/610:07 am
BOS
- MCO
Nonstop3h 23m
Frontier
Sat 5/96:00 am
MCO
- BOS
Nonstop3h 12m
Frontier
Deal found 3/30![Frontier logo]()
$143
This Frontier deal was found by Cheapflights users on 3/27. 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 4/125:30 am
BOS
- MCO
1 stop8h 49m
Frontier
Wed 4/157:05 am
MCO
- BOS
Nonstop3h 16m
Frontier
Deal found 3/27![Frontier logo]()
$144
This Gotogate deal was found by Cheapflights users on 3/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:31 pm
BOS
- MCO
1 stop24h 03m
Frontier
Wed 5/136:00 am
MCO
- BOS
Nonstop3h 12m
Frontier
Deal found 3/29![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 4/134:23 pm
BOS
- MCO
Nonstop3h 13m
Multiple Airlines
Thu 4/167:00 am
MCO
- BOS
Nonstop3h 16m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Fri 5/16:00 am
BOS
- MCO
1 stop7h 58m
Frontier
Thu 5/76:00 am
MCO
- BOS
Nonstop3h 12m
Frontier
Deal found 3/27![Frontier logo]()
$147
This Frontier deal was found by Cheapflights users on 3/27. 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 5/111:06 am
BOS
- MCO
Nonstop3h 24m
Frontier
Wed 5/66:00 am
MCO
- BOS
Nonstop3h 12m
Frontier
Deal found 3/27![Frontier logo]()
$148
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:20 am
BOS
- MCO
Nonstop3h 09m
Spirit Airlines
Sat 5/306:36 pm
MCO
- BOS
Nonstop3h 06m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 3/31. 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.
Mon 6/17:00 am
BOS
- MCO
Nonstop3h 10m
Spirit Airlines
Wed 6/104:10 pm
MCO
- BOS
Nonstop3h 05m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 5/97:00 am
BOS
- MCO
Nonstop3h 10m
Spirit Airlines
Sat 5/96:36 pm
MCO
- BOS
Nonstop3h 06m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$151
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 April 1, 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 April 1, 2026.
This Delta deal was found by Cheapflights users on 3/31. 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 5/233:30 pm
BOS
- MCO
Nonstop3h 24m
Delta
Sat 5/306:00 am
MCO
- BOS
1 stop5h 10m
Delta
Deal found 3/31![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/27. 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.
Mon 5/410:40 am
BOS
- MCO
2 stops8h 25m
Southwest
Wed 5/68:55 am
MCO
- BOS
2 stops7h 10m
Southwest
Deal found 3/27![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 3/29. 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.
Wed 6/36:00 am
BOS
- MCO
2 stops8h 47m
United Airlines
Wed 6/37:05 pm
MCO
- BOS
1 stop4h 54m
United Airlines
Deal found 3/29![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 3/28. 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 5/611:40 am
BOS
- MCO
2 stops7h 15m
Southwest
Sat 5/91:40 pm
MCO
- BOS
2 stops7h 45m
Southwest
Deal found 3/28![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 3/31. 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 5/99:25 am
BOS
- MCO
2 stops8h 30m
Southwest
Wed 5/133:25 pm
MCO
- BOS
2 stops7h 05m
Southwest
Deal found 3/31![Southwest logo]()
$257
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Mon 4/1310:05 am
BOS
- MCO
2 stops11h 53m
United Airlines
Sat 4/189:03 am
MCO
- BOS
2 stops11h 51m
United Airlines
Deal found 3/27![United Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 3/31. 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 5/2011:40 am
BOS
- MCO
2 stops7h 15m
Southwest
Fri 5/225:10 pm
MCO
- BOS
1 stop6h 05m
Southwest
Deal found 3/31![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 3/29. 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.
Fri 6/56:00 am
BOS
- MCO
2 stops8h 43m
United Airlines
Thu 6/119:40 am
MCO
- BOS
1 stop6h 49m
United Airlines
Deal found 3/29![United Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 3/29. 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.
Mon 5/117:25 pm
BOS
- MCO
1 stop4h 40m
Southwest
Thu 5/142:20 pm
MCO
- BOS
2 stops8h 00m
Southwest
Deal found 3/29![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 3/27. 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 5/169:25 am
BOS
- MCO
2 stops8h 30m
Southwest
Sat 5/231:40 pm
MCO
- BOS
2 stops7h 45m
Southwest
Deal found 3/27![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 3/30. 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.
Sun 5/39:10 am
BOS
- MCO
2 stops7h 35m
Southwest
Sun 5/310:55 pm
MCO
- BOS
1 stop9h 10m
Southwest
Deal found 3/30![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 3/27. 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.
Thu 5/710:40 am
BOS
- MCO
2 stops8h 25m
Southwest
Mon 5/119:05 am
MCO
- BOS
2 stops9h 00m
Southwest
Deal found 3/27![Southwest logo]()
$393
Last-minute flights from Boston to KissimmeeDiscover last-minute flight deals from Boston to Kissimmee. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Kissimmee. Data last updated April 1, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 3/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:42 pm
BOS
- MCO
1 stop7h 39m
Frontier
Thu 4/167:00 am
MCO
- BOS
Nonstop3h 16m
Frontier
Deal found 3/29![Frontier logo]()
$150
This Super.com deal was found by Cheapflights users on 4/1. 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 4/85:45 am
BOS
- MCO
1 stop8h 40m
Frontier
Wed 4/157:05 am
MCO
- BOS
Nonstop3h 16m
Frontier
Deal found 4/1![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 4/1. 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 4/911:26 am
BOS
- MCO
Nonstop3h 24m
Frontier
Wed 4/153:20 pm
MCO
- BOS
1 stop20h 13m
Frontier
Deal found 4/1![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/117:14 pm
BOS
- MCO
Nonstop3h 17m
Multiple Airlines
Thu 4/167:00 am
MCO
- BOS
Nonstop3h 16m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/117:14 pm
BOS
- MCO
Nonstop3h 17m
Multiple Airlines
Tue 4/147:05 am
MCO
- BOS
Nonstop3h 16m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$143
This Frontier deal was found by Cheapflights users on 3/28. 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 4/1112:40 pm
BOS
- MCO
1 stop8h 51m
Frontier
Thu 4/167:00 am
MCO
- BOS
Nonstop3h 16m
Frontier
Deal found 3/28![Frontier logo]()
$144
This Orbitz deal was found by Cheapflights users on 3/31. 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 4/1112:06 pm
BOS
- MCO
Nonstop3h 27m
Multiple Airlines
Wed 4/157:40 am
MCO
- BOS
1 stop5h 27m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$146
This CheapOair deal was found by Cheapflights users on 3/28. 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 4/117:14 pm
BOS
- MCO
Nonstop3h 17m
Multiple Airlines
Sat 4/187:05 am
MCO
- BOS
Nonstop3h 16m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/1112:06 pm
BOS
- MCO
Nonstop3h 27m
Frontier
Wed 4/153:20 pm
MCO
- BOS
1 stop20h 13m
Frontier
Deal found 3/31![Frontier logo]()
$157
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 April 1, 2026.
Search for one-way flight options from Boston to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Super.com deal was found by Cheapflights users on 4/1. 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 4/511:31 am
BOS
- MCO
Nonstop3h 24m
Frontier
Deal found 4/1![Frontier logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Sun 5/317:00 am
BOS
- MCO
Nonstop3h 10m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$74
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:57 pm
BOS
- MCO
Nonstop3h 14m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/2712:31 pm
BOS
- MCO
1 stop10h 06m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$77
This Orbitz deal was found by Cheapflights users on 3/29. 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.
Mon 4/273:27 pm
BOS
- MCO
Nonstop3h 16m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$78
This Super.com deal was found by Cheapflights users on 3/31. 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 4/286:00 am
BOS
- MCO
1 stop7h 34m
Frontier
Deal found 3/31![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/307:00 am
BOS
- MCO
Nonstop3h 10m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$80
This Super.com deal was found by Cheapflights users on 3/31. 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 4/205:45 am
BOS
- MCO
1 stop14h 00m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$81
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:16 pm
BOS
- MCO
1 stop13h 56m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$83
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:18 am
BOS
- MCO
1 stop14h 02m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$84
This Super.com deal was found by Cheapflights users on 3/27. 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 4/2312:31 pm
BOS
- MCO
1 stop12h 13m
Frontier
Deal found 3/27![Frontier logo]()
$85
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 April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $141 (Kiwi.com) |
One-way from | $73 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $332 |
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 April 1, 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
Quickest round-trip
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 5/23
3:30 pm-6:54 pm
Nonstop3h 24m
Orlando
Sat 5/30
6:00 am-11:10 am
1 stop5h 10m
$237
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Mon 5/4
10:40 am-7:05 pm
2 stops8h 25m
Orlando
Wed 5/6
8:55 am-4:05 pm
2 stops7h 10m
$257
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Wed 5/6
11:40 am-6:55 pm
2 stops7h 15m
Orlando
Sat 5/9
1:40 pm-9:25 pm
2 stops7h 45m
$257
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 5/9
9:25 am-5:55 pm
2 stops8h 30m
Orlando
Wed 5/13
3:25 pm-10:30 pm
2 stops7h 05m
$257
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Wed 5/20
11:40 am-6:55 pm
2 stops7h 15m
Orlando
Fri 5/22
5:10 pm-11:15 pm
1 stop6h 05m
$317
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Mon 5/11
7:25 pm-12:05 am
1 stop4h 40m
Orlando
Thu 5/14
2:20 pm-10:20 pm
2 stops8h 00m
$333
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sat 5/16
9:25 am-5:55 pm
2 stops8h 30m
Orlando
Sat 5/23
1:40 pm-9:25 pm
2 stops7h 45m
$337
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Wed 6/3
6:00 am-2:47 pm
2 stops8h 47m
Orlando
Wed 6/3
7:05 pm-11:59 pm
1 stop4h 54m
$342
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Sun 5/3
9:10 am-4:45 pm
2 stops7h 35m
Orlando
Sun 5/3
10:55 pm-8:05 am
1 stop9h 10m
$358
BostonOrlando
BOS - MCO
BOSMCO
Boston Logan Intl
Mon 4/13
10:05 am-9:58 pm
2 stops11h 53m
Orlando
Sat 4/18
9:03 am-8:54 pm
2 stops11h 51m
$372
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
How far ahead should I book a flight from Boston to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from Boston to Kissimmee. Price data was last updated on March 13, 2026.
The price you pay for your flight from Boston to Kissimmee may vary depending on when you book. For the best chance of a lower fare, look to book 15 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Boston to Kissimmee?
Currently, September is the cheapest month in which you can book a flight from Boston to Kissimmee (average of $56). Flying from Boston to Kissimmee in June is currently the most expensive (average of $88). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 April 1, 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 5% on airfare.
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 March 28, 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. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 1, 2026.
The most flights from BOS to K1S are scheduled on a Tuesday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).
How much does it cost to fly round-trip from Boston to Kissimmee?
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 April 1, 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.
Food
7.2
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Food
7.2
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Food
7.2
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Food
7.2
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Food
7.2
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
Food
7.2
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Overall
7.9
Crew
8.5
Reviews
1 / 20
2.0
MediocreJoseph,Aug 2023
MSP - MCO
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 April 1, 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 April 1, 2026.
Popular flight searches
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Boston to Kissimmee flights
Consider these flights traveling from Boston to Kissimmee.
Top 10 airlines flying from Boston to Kissimmee
Discover the top 10 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$51 | Average$172 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$59 | Average$165 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$205 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$95 | Average$235 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$117 | Average$304 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$335 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$150 | Average$339 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$166 | Average$261 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$177 | Average$359 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$307 | FlexibilityNo cancel fee | On-time69% |