$104+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Sep 16 — Sep 231
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 August 17, 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 August 17, 2026.
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
Nonstop3h 09m
Sat 9/1211:36 am -
Nonstop3h 16m
Deal found 8/15![Frontier logo]()
$191
This Super.com deal was found by Cheapflights users on 8/16. 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.
Mon 10/197:45 am -
Nonstop3h 17m
Sat 10/2411:47 am -
Nonstop3h 23m
Deal found 8/16![Frontier logo]()
$192
This CheapOair deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 am -
Nonstop3h 17m
Mon 10/2611:47 am -
Nonstop3h 23m
Deal found 8/12![Frontier logo]()
$193
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:45 am -
Nonstop3h 06m
Fri 9/2511:36 am -
Nonstop3h 16m
Deal found 8/15![Frontier logo]()
$195
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
Nonstop3h 16m
Sat 10/3111:05 am -
Nonstop3h 34m
Deal found 8/13![Frontier logo]()
$199
This Frontier deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
Nonstop3h 09m
Sat 11/1411:05 am -
Nonstop3h 34m
Deal found 8/12![Frontier logo]()
$200
This Super.com deal was found by Cheapflights users on 8/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:45 am -
Nonstop3h 17m
Fri 10/1611:47 am -
Nonstop3h 23m
Deal found 8/14![Frontier logo]()
$201
This Priceline deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:45 am -
Nonstop3h 17m
Sat 10/1711:47 am -
Nonstop3h 23m
Deal found 8/12![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:21 pm -
2 stops14h 29m
Sat 9/1211:36 am -
Nonstop3h 16m
Deal found 8/15![Frontier logo]()
$203
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:16 am -
Nonstop3h 06m
Thu 10/111:17 am -
Nonstop3h 16m
Deal found 8/13![Frontier logo]()
$204
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 August 17, 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 August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:55 am -
1 stop5h 10m
Tue 9/222:45 pm -
1 stop6h 25m
Deal found 8/12![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:59 pm -
Nonstop3h 08m
Wed 10/1411:25 am -
Nonstop3h 10m
Deal found 8/14![Delta logo]()
$250
This Southwest deal was found by Cheapflights users on 8/16. 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 9/154:00 pm -
1 stop6h 15m
Tue 9/222:45 pm -
1 stop6h 25m
Deal found 8/16![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:59 pm -
Nonstop3h 08m
Sun 10/117:10 am -
Nonstop3h 18m
Deal found 8/14![Delta logo]()
$250
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/128:00 am -
1 stop6h 10m
Sat 9/1912:10 pm -
1 stop6h 00m
Deal found 8/13![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:51 pm -
1 stop7h 17m
Tue 10/136:00 am -
1 stop6h 44m
Deal found 8/15![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 8/15. 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 9/811:20 am -
1 stop4h 40m
Tue 9/155:25 am -
2 stops6h 50m
Deal found 8/15![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 8/16. 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.
Mon 12/2111:00 am -
Nonstop3h 02m
Thu 12/317:00 am -
Nonstop3h 27m
Deal found 8/16![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:10 am -
Nonstop3h 04m
Thu 12/37:54 pm -
Nonstop3h 24m
Deal found 8/13![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 8/16. 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 9/164:00 pm -
1 stop6h 15m
Thu 9/2412:40 pm -
2 stops7h 35m
Deal found 8/16![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 8/16. 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 9/54:05 pm -
1 stop7h 54m
Sun 9/67:05 am -
Nonstop3h 06m
Deal found 8/16![Delta logo]()
$301
Last-minute flights from Kissimmee to BostonDiscover last-minute flight deals from Kissimmee to Boston. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Boston. Data last updated August 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:21 pm -
2 stops14h 29m
Sat 9/1211:36 am -
Nonstop3h 16m
Deal found 8/15![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
Nonstop3h 09m
Sat 9/1211:36 am -
Nonstop3h 16m
Deal found 8/15![Frontier logo]()
$191
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:45 am -
Nonstop3h 06m
Fri 9/2511:36 am -
Nonstop3h 16m
Deal found 8/15![Frontier logo]()
$195
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:55 am -
1 stop5h 10m
Tue 9/222:45 pm -
1 stop6h 25m
Deal found 8/12![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:16 am -
Nonstop3h 06m
Mon 9/2111:36 am -
Nonstop3h 16m
Deal found 8/16![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:16 am -
Nonstop3h 06m
Thu 10/111:17 am -
Nonstop3h 16m
Deal found 8/13![Frontier logo]()
$204
This JetBlue deal was found by Cheapflights users on 8/15. 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.
Tue 9/298:10 pm -
Nonstop3h 08m
Tue 10/67:10 pm -
Nonstop3h 24m
Deal found 8/15![JetBlue logo]()
$209
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 August 17, 2026.
Search for one-way flight options from Kissimmee to Boston. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:15 am -
1 stop6h 35m
Deal found 8/12![Southwest logo]()
$104
This Trip.com deal was found by Cheapflights users on 8/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/117:45 am -
Nonstop3h 17m
Deal found 8/16![Frontier logo]()
$105
This Faresmojo deal was found by Cheapflights users on 8/15. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:50 pm -
1 stop7h 25m
Deal found 8/15![JetBlue logo]()
$106
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:50 am -
2 stops7h 00m
Deal found 8/12![Southwest logo]()
$109
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:53 am -
1 stop9h 26m
Deal found 8/16![United Airlines logo]()
$110
This Super.com deal was found by Cheapflights users on 8/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/167:40 am -
1 stop6h 26m
Deal found 8/14![JetBlue logo]()
$111
This Super.com deal was found by Cheapflights users on 8/16. 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.
Tue 10/612:45 pm -
1 stop6h 31m
Deal found 8/16![JetBlue logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am -
2 stops29h 47m
Deal found 8/12![Frontier logo]()
$114
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:20 pm -
1 stop5h 39m
Deal found 8/16![United Airlines logo]()
$115
This Frontier deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/147:00 am -
Nonstop3h 09m
Deal found 8/12![Frontier logo]()
$116
This Jetabroad deal was found by Cheapflights users on 8/15. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:15 pm -
1 stop4h 42m
Deal found 8/15![JetBlue logo]()
$117
This Southwest deal was found by Cheapflights users on 8/13. 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.
Thu 10/222:05 pm -
1 stop7h 00m
Deal found 8/13![Southwest logo]()
$118
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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $191 (Frontier) |
One-way from | $104 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $286 |
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 August 17, 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
Wed 9/16
11:55 am-5:05 pm
1 stop5h 10m
Boston Logan Intl
Tue 9/22
2:45 pm-9:10 pm
1 stop6h 25m
$207
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Tue 9/15
4:00 pm-10:15 pm
1 stop6h 15m
Boston Logan Intl
Tue 9/22
2:45 pm-9:10 pm
1 stop6h 25m
$229
Quickest round-trip
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 10/7
7:59 pm-11:07 pm
Nonstop3h 08m
Boston Logan Intl
Wed 10/14
11:25 am-2:35 pm
Nonstop3h 10m
$250
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 10/7
7:59 pm-11:07 pm
Nonstop3h 08m
Boston Logan Intl
Sun 10/11
7:10 am-10:28 am
Nonstop3h 18m
$250
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 9/12
8:00 am-2:10 pm
1 stop6h 10m
Boston Logan Intl
Sat 9/19
12:10 pm-6:10 pm
1 stop6h 00m
$270
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 10/7
3:51 pm-11:08 pm
1 stop7h 17m
Boston Logan Intl
Tue 10/13
6:00 am-12:44 pm
1 stop6h 44m
$270
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Tue 9/8
11:20 am-4:00 pm
1 stop4h 40m
Boston Logan Intl
Tue 9/15
5:25 am-12:15 pm
2 stops6h 50m
$275
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Mon 12/21
11:00 am-2:02 pm
Nonstop3h 02m
Boston Logan Intl
Thu 12/31
7:00 am-10:27 am
Nonstop3h 27m
$291
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Mon 11/23
7:10 am-10:14 am
Nonstop3h 04m
Boston Logan Intl
Thu 12/3
7:54 pm-11:18 pm
Nonstop3h 24m
$291
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 9/16
4:00 pm-10:15 pm
1 stop6h 15m
Boston Logan Intl
Thu 9/24
12:40 pm-8:15 pm
2 stops7h 35m
$299
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 August 17, 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 August 17, 2026.
The most flights from K1S to BOS are scheduled on a Sunday (49 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (25 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 $225 and $359 in September.The cheapest round-trip price found within the last 5 days was $191 on Frontier (Sep 10-Sep 12).
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 August 15, 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 August 17, 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.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
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
Seekonk
Cranston
Dedham
Warwick
Peabody
Auburn
Chelsea
York Beach
Londonderry
Revere
Fitchburg
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North Falmouth
Braintree
Sandwich
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Alternative routes for Kissimmee to Boston
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Other flights to Boston
Explore flights to Boston departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 17, 2026.
Complete your trip
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Kissimmee and Boston flights
Browse other Kissimmee and Boston flight options. Last updated on August 17, 2026.
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Kissimmee to Boston flights
Consider these flights traveling from Kissimmee to Boston.
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 August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$47 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$117 | Average$287 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$297 | 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$315 | FlexibilityNo cancel fee | On-time71% |