$113+ Cheap flights from Kissimmee, FL to Boston (BOS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Oct 19 — Oct 261
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 September 19, 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 September 19, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/65:35 pm -
1 stop5h 10m
Wed 10/710:55 am -
1 stop9h 20m
Deal found 9/15![Southwest logo]()
$204
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:00 am -
Nonstop3h 00m
Sat 10/1711:47 am -
Nonstop3h 23m
Deal found 9/17![Multiple Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
Nonstop3h 10m
Tue 11/107:54 pm -
Nonstop3h 22m
Deal found 9/16![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 9/14. 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 11/31:45 pm -
2 stops8h 05m
Sat 11/149:30 am -
2 stops9h 25m
Deal found 9/14![Southwest logo]()
$209
This flygcity.se deal was found by Cheapflights users on 9/14. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 pm -
Nonstop3h 30m
Mon 10/267:35 pm -
Nonstop3h 24m
Deal found 9/14![JetBlue logo]()
$210
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:00 am -
Nonstop3h 00m
Wed 11/45:30 am -
1 stop6h 27m
Deal found 9/14![JetBlue logo]()
$211
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:45 am -
Nonstop3h 17m
Sat 10/1711:47 am -
Nonstop3h 23m
Deal found 9/16![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 9/14. 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 10/149:15 am -
1 stop5h 40m
Wed 10/214:15 pm -
1 stop5h 55m
Deal found 9/14![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:05 am -
1 stop4h 50m
Sat 10/249:40 am -
1 stop11h 20m
Deal found 9/16![Southwest logo]()
$216
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:15 am -
1 stop7h 44m
Sun 11/18:35 pm -
Nonstop3h 24m
Deal found 9/17![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:16 pm -
1 stop5h 43m
Sat 10/177:25 pm -
Nonstop3h 20m
Deal found 9/17![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
Nonstop3h 10m
Tue 10/138:15 pm -
Nonstop3h 15m
Deal found 9/16![Delta logo]()
$219
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 September 19, 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 September 19, 2026.
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:59 pm -
Nonstop3h 08m
Mon 11/95:40 pm -
Nonstop3h 23m
Deal found 9/17![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 9/14. 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 11/268:25 am -
1 stop8h 05m
Tue 12/15:45 pm -
1 stop5h 45m
Deal found 9/14![Southwest logo]()
$253
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/102:25 pm -
Nonstop3h 35m
Sun 10/115:30 am -
1 stop5h 44m
Deal found 9/13![JetBlue logo]()
$262
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:32 pm -
1 stop7h 03m
Wed 11/1112:00 pm -
1 stop6h 24m
Deal found 9/14![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/43:40 pm -
Nonstop3h 09m
Sat 11/77:25 pm -
Nonstop3h 20m
Deal found 9/16![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:35 pm -
2 stops8h 25m
Mon 12/75:45 pm -
1 stop5h 40m
Deal found 9/14![Southwest logo]()
$258
This JetBlue deal was found by Cheapflights users on 9/15. 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.
Thu 10/299:15 am -
1 stop7h 44m
Sun 11/17:35 pm -
Nonstop3h 24m
Deal found 9/15![JetBlue logo]()
$275
This Southwest deal was found by Cheapflights users on 9/15. 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 12/23:35 pm -
1 stop6h 40m
Thu 12/32:35 pm -
1 stop8h 55m
Deal found 9/15![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:51 pm -
1 stop7h 14m
Sun 11/86:00 am -
1 stop6h 44m
Deal found 9/16![Delta logo]()
$268
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:30 pm -
Nonstop3h 30m
Thu 10/156:40 pm -
1 stop5h 19m
Deal found 9/13![JetBlue logo]()
$275
This Southwest deal was found by Cheapflights users on 9/14. 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 12/49:10 am -
1 stop5h 20m
Mon 12/75:30 am -
1 stop6h 05m
Deal found 9/14![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:25 pm -
1 stop7h 45m
Mon 10/266:20 am -
1 stop7h 09m
Deal found 9/17![Delta logo]()
$299
Last-minute flights from Kissimmee to BostonDiscover last-minute flight deals from Kissimmee to Boston. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Boston. Data last updated September 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/65:35 pm -
1 stop5h 10m
Wed 10/710:55 am -
1 stop9h 20m
Deal found 9/15![Southwest logo]()
$204
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:00 am -
Nonstop3h 10m
Tue 10/138:15 pm -
Nonstop3h 15m
Deal found 9/16![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:16 pm -
1 stop5h 43m
Sat 10/177:25 pm -
Nonstop3h 20m
Deal found 9/17![Delta logo]()
$218
This Expedia deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1410:00 am -
Nonstop3h 00m
Sat 10/1711:47 am -
Nonstop3h 23m
Deal found 9/17![Multiple Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:59 pm -
Nonstop3h 08m
Wed 10/217:10 am -
Nonstop3h 18m
Deal found 9/17![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 9/14. 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 10/149:15 am -
1 stop5h 40m
Wed 10/214:15 pm -
1 stop5h 55m
Deal found 9/14![Southwest logo]()
$215
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:45 am -
Nonstop3h 17m
Sat 10/1711:47 am -
Nonstop3h 23m
Deal found 9/16![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:05 am -
1 stop4h 50m
Sat 10/249:40 am -
1 stop11h 20m
Deal found 9/16![Southwest logo]()
$216
This flygcity.se deal was found by Cheapflights users on 9/14. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:30 pm -
Nonstop3h 30m
Mon 10/267:35 pm -
Nonstop3h 24m
Deal found 9/14![JetBlue logo]()
$210
This Southwest deal was found by Cheapflights users on 9/15. 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 10/272:05 pm -
2 stops7h 25m
Tue 11/311:20 am -
2 stops8h 40m
Deal found 9/15![Southwest logo]()
$209
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:15 am -
1 stop7h 44m
Sun 11/18:35 pm -
Nonstop3h 24m
Deal found 9/17![JetBlue logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:00 am -
Nonstop3h 00m
Wed 11/45:30 am -
1 stop6h 27m
Deal found 9/14![JetBlue logo]()
$211
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 September 19, 2026.
Search for one-way flight options from Kissimmee to Boston. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:00 am -
Nonstop3h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$113
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:35 pm -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$116
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/152:35 pm -
1 stop4h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:15 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:03 pm -
2 stops40h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$126
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:30 am -
2 stops7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$127
This Super.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:50 am -
Nonstop3h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$128
This Super.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:01 am -
Nonstop3h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$129
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 September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Southwest) |
One-way from | $113 (KAYAK) |
Popular in | July |
Cheapest in | January |
Average price | $291 |
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 7,457,451 searches. Data last updated September 19, 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 Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 12/5
6:15 am-12:50 pm
1 stop6h 35m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$120
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Mon 11/2
7:25 am-5:10 pm
1 stop9h 45m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$138
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Mon 11/9
9:05 am-3:40 pm
2 stops6h 35m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$143
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 11/11
7:00 am-5:27 pm
2 stops10h 27m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$150
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 10/14
12:33 pm-10:45 pm
2 stops10h 12m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$150
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Fri 12/11
6:10 am-1:45 pm
1 stop7h 35m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$154
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 11/21
2:10 pm-9:20 pm
2 stops7h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$191
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Fri 11/13
9:52 am-9:59 pm
2 stops12h 07m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$200
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Thu 10/15
10:40 am-5:20 pm
2 stops6h 40m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sun 11/22
4:25 pm-11:45 pm
2 stops7h 20m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$213
Showing 1-10 of 23 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 September 19, 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 57% 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 September 19, 2026.
The most flights from K1S to BOS are scheduled on a Thursday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Kissimmee to Boston?
Airfare is typical for this route at the moment.
Kissimmee to Boston flights typically cost between $204 and $348 in October.The cheapest round-trip price found within the last 5 days was $204 on Southwest (Oct 6-Oct 7).
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 September 12, 2026.
Travelers seeking maximum savings on their Kissimmee to Boston flight should consider departing on Tuesday 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 September 19, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andJetBlue 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.
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
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
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Revere
Warwick
Pawtucket
Peabody
Auburn
Londonderry
York Beach
Fitchburg
North Falmouth
Swansea
Chelsea
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 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$54 | Average$231 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$120 | Average$355 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$125 | Average$310 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$297 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$184 | Average$435 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$192 | Average$382 | FlexibilityNo cancel fee | On-time71% |