$99+ Cheap flights from Kissimmee, FL to Boston (BOS)
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from Kissimmee to Boston 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 Kissimmee to Boston Logan Intl are usually found in January or February, booked 44 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Kissimmee to Boston
Cheapest
Best
Last-minute
One-way
Cheapest flights from Kissimmee to BostonExplore the most affordable flight options available from Kissimmee to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
Explore the most affordable flight options available from Kissimmee to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Thu 8/276:25 am
MCO
- BOS
1 stop5h 25m
Frontier
Mon 8/3110:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/18![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Thu 9/107:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Mon 9/1411:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Deal found 7/19![Frontier logo]()
$183
This Booking.com deal was found by Cheapflights users on 7/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:24 am
MCO
- BOS
1 stop6h 23m
Frontier
Sat 9/1211:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Deal found 7/20![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/276:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Sat 9/510:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/22![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/276:25 am
MCO
- BOS
1 stop5h 25m
Frontier
Fri 9/410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/20![Frontier logo]()
$188
This FlightHub deal was found by Cheapflights users on 7/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Mon 9/1411:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Deal found 7/20![Frontier logo]()
$189
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Sat 9/1211:05 am
BOS
- MCO
Nonstop3h 34m
Frontier
Deal found 7/19![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 10/225:15 am
MCO
- BOS
Nonstop3h 05m
Frontier
Mon 10/269:15 am
BOS
- MCO
Nonstop3h 22m
Frontier
Deal found 7/20![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/246:25 am
MCO
- BOS
1 stop5h 25m
Frontier
Thu 8/2712:45 pm
BOS
- MCO
1 stop11h 14m
Frontier
Deal found 7/19![Frontier logo]()
$194
This Trip.com deal was found by Cheapflights users on 7/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/85:15 am
MCO
- BOS
Nonstop3h 05m
Frontier
Sun 10/119:15 am
BOS
- MCO
Nonstop3h 22m
Frontier
Deal found 7/20![Frontier logo]()
$195
Best flights from Kissimmee to BostonDiscover carefully curated flight deals from Kissimmee to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
Discover carefully curated flight deals from Kissimmee to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 11/410:05 am
MCO
- BOS
1 stop4h 20m
Southwest
Sat 11/79:00 am
BOS
- MCO
1 stop9h 50m
Southwest
Deal found 7/21![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 9/26:00 pm
MCO
- BOS
1 stop5h 59m
Delta
Mon 9/77:05 am
BOS
- MCO
Nonstop3h 06m
Delta
Deal found 7/20![Delta logo]()
$240
This United Airlines deal was found by Cheapflights users on 7/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2311:04 am
MCO
- BOS
1 stop5h 44m
United Airlines
Fri 10/26:00 am
BOS
- MCO
1 stop5h 50m
United Airlines
Deal found 7/20![United Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
MCO
- BOS
1 stop5h 15m
Delta
Sun 8/238:20 pm
BOS
- MCO
Nonstop3h 14m
Delta
Deal found 7/19![Delta logo]()
$240
This Southwest deal was found by Cheapflights users on 7/18. 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.
Sat 9/59:35 am
MCO
- BOS
1 stop9h 20m
Southwest
Tue 9/810:50 am
BOS
- MCO
2 stops7h 10m
Southwest
Deal found 7/18![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:45 am
MCO
- BOS
1 stop6h 57m
Delta
Mon 10/58:20 pm
BOS
- MCO
Nonstop3h 15m
Delta
Deal found 7/19![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 7/22. 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 12/47:35 am
MCO
- BOS
1 stop6h 50m
Southwest
Sat 12/59:30 am
BOS
- MCO
2 stops9h 45m
Southwest
Deal found 7/22![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:43 pm
MCO
- BOS
Nonstop3h 08m
Delta
Mon 10/126:00 am
BOS
- MCO
1 stop6h 44m
Delta
Deal found 7/19![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 7/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:27 pm
MCO
- BOS
1 stop5h 31m
Delta
Mon 10/56:20 am
BOS
- MCO
1 stop7h 04m
Delta
Deal found 7/19![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 7/22. 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 10/308:00 am
MCO
- BOS
1 stop5h 47m
Delta
Sun 11/17:59 pm
BOS
- MCO
Nonstop3h 16m
Delta
Deal found 7/22![Delta logo]()
$281
This Delta deal was found by Cheapflights users on 7/21. 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 8/156:59 pm
MCO
- BOS
1 stop6h 26m
Delta
Tue 9/17:25 am
BOS
- MCO
1 stop5h 34m
Delta
Deal found 7/21![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 7/22. 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 9/1211:23 am
MCO
- BOS
Nonstop3h 06m
Delta
Sat 9/197:05 am
BOS
- MCO
Nonstop3h 13m
Delta
Deal found 7/22![Delta logo]()
$309
Last-minute flights from Kissimmee to BostonDiscover last-minute flight deals from Kissimmee to Boston. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Boston. Data last updated July 23, 2026 and is based on user searches.
This Jetabroad deal was found by Cheapflights users on 7/21. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 8/1912:45 pm
BOS
- MCO
1 stop5h 48m
Frontier
Deal found 7/21![Frontier logo]()
$248
This Frontier deal was found by Cheapflights users on 7/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 8/411:52 am
BOS
- MCO
1 stop10h 23m
Frontier
Deal found 7/20![Frontier logo]()
$269
This Frontier deal was found by Cheapflights users on 7/18. 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 7/296:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 8/1110:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/18![Frontier logo]()
$240
This Frontier deal was found by Cheapflights users on 7/22. 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 7/296:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 8/1210:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/22![Frontier logo]()
$255
This Frontier deal was found by Cheapflights users on 7/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Mon 8/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/20![Frontier logo]()
$244
This Super.com deal was found by Cheapflights users on 7/22. 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 8/16:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Mon 8/3110:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/22![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 7/18. 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.
Sat 8/16:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 8/410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/18![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Thu 8/2010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/19![Frontier logo]()
$271
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Mon 8/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 7/19![Frontier logo]()
$272
One-way flights from Kissimmee to BostonSearch for one-way flight options from Kissimmee to Boston. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
Search for one-way flight options from Kissimmee to Boston. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/246:25 am
MCO
- BOS
1 stop5h 25m
Frontier
Deal found 7/19![Frontier logo]()
$99
This Super.com deal was found by Cheapflights users on 7/22. 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 11/147:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/22![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 7/22. 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 8/296:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/22![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 7/19. 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.
Tue 7/286:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/19![Frontier logo]()
$104
This Frontier deal was found by Cheapflights users on 7/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/19![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/257:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/22![Frontier logo]()
$106
This eDestinos deal was found by Cheapflights users on 7/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/19![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 7/19. 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.
Sun 8/166:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/19![Frontier logo]()
$108
This CheapOair deal was found by Cheapflights users on 7/20. 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.
Sun 8/306:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 7/20![Frontier logo]()
$109
This Southwest deal was found by Cheapflights users on 7/21. 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 8/252:50 pm
MCO
- BOS
1 stop7h 20m
Southwest
Deal found 7/21![Southwest logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/276:25 am
MCO
- BOS
1 stop5h 25m
Frontier
Deal found 7/22![Frontier logo]()
$111
Find flight deals from Kissimmee to Boston
Keep the following information in mind while searching for Kissimmee to Boston flight deals. Data was last updated July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Kiwi.com) |
One-way from | $99 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $304 |
Cheapflights Fare Finder
Customize your flight search to find flights from Kissimmee to Boston 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 July 23, 2026.
Use the filters below to find and compare flights from Kissimmee to Boston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Wed 11/4
10:05 am-2:25 pm
1 stop4h 20m
Boston Logan Intl
Sat 11/7
9:00 am-6:50 pm
1 stop9h 50m
$234
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Wed 9/2
6:00 pm-11:59 pm
1 stop5h 59m
Boston Logan Intl
Mon 9/7
7:05 am-10:11 am
Nonstop3h 06m
$240
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Tue 8/18
6:00 am-11:15 am
1 stop5h 15m
Boston Logan Intl
Sun 8/23
8:20 pm-11:34 pm
Nonstop3h 14m
$240
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Wed 9/23
11:04 am-4:48 pm
1 stop5h 44m
Boston Logan Intl
Fri 10/2
6:00 am-11:50 am
1 stop5h 50m
$250
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Fri 10/2
7:45 am-2:42 pm
1 stop6h 57m
Boston Logan Intl
Mon 10/5
8:20 pm-11:35 pm
Nonstop3h 15m
$271
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Fri 10/9
3:43 pm-6:51 pm
Nonstop3h 08m
Boston Logan Intl
Mon 10/12
6:00 am-12:44 pm
1 stop6h 44m
$271
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Thu 10/1
6:27 pm-11:58 pm
1 stop5h 31m
Boston Logan Intl
Mon 10/5
6:20 am-1:24 pm
1 stop7h 04m
$281
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Fri 10/30
8:00 am-1:47 pm
1 stop5h 47m
Boston Logan Intl
Sun 11/1
7:59 pm-11:15 pm
Nonstop3h 16m
$281
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 8/15
6:59 pm-1:25 am
1 stop6h 26m
Boston Logan Intl
Tue 9/1
7:25 am-12:59 pm
1 stop5h 34m
$291
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 9/5
9:35 am-6:55 pm
1 stop9h 20m
Boston Logan Intl
Tue 9/8
10:50 am-6:00 pm
2 stops7h 10m
$292
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from Kissimmee to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston from Kissimmee with our price prediction graph.
MCO-BOS
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 Kissimmee to Boston
K1S-BOS
MCO-BOS
What is the cheapest time of day to fly from K1S to BOS?
Find hourly flight availability from Kissimmee to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 23, 2026.
A simple way to save on the total cost of your ticket is to fly from Kissimmee to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 61% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Kissimmee to Boston
Explore weekly flight availability from Kissimmee to Boston. 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 July 23, 2026.
The most flights from K1S to BOS are scheduled on a Wednesday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
How much does it cost to fly round-trip from Kissimmee to Boston?
Airfare is below average for this route at the moment.
Kissimmee to Boston flights typically cost between $183 and $344 in August.The cheapest round-trip price found within the last 5 days was $182 on Frontier (Aug 27-Aug 31).
What is the cheapest day to fly from Kissimmee to Boston?
Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Boston. Price data was last updated on July 18, 2026.
Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Wednesday evenings 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 Boston
Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated July 23, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican Airlines from Kissimmee to Boston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Kissimmee to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Cambridge
Concord
Randolph
Brockton
Seekonk
Hampton Beach
Cranston
Dedham
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Sandwich
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Other flights to Boston
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Kissimmee and Boston flights
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Top 7 airlines flying from Kissimmee to Boston
Discover the top 7 airlines that operate flights from Kissimmee to Boston. 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$44 | Average$169 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$114 | Average$277 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$287 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$347 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$184 | Average$386 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$192 | Average$353 | FlexibilityNo cancel fee | On-time71% |