$102+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BOS
Jul 23 — Jul 301
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
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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 June 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 June 23, 2026.
This CheapOair deal was found by Cheapflights users on 6/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:40 am
MCO
- BOS
1 stop7h 37m
Multiple Airlines
Sat 8/2910:04 am
BOS
- MCO
Nonstop3h 36m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$174
This Frontier deal was found by Cheapflights users on 6/22. 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 8/126:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 8/1211:59 am
BOS
- MCO
1 stop6h 34m
Frontier
Deal found 6/22![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 6/22. 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.
Sat 7/116:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Mon 7/1310:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/22![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
Mon 7/206:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 7/2210:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/18![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 6/19. 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 7/96:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 7/1410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/19![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 6/23. 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 8/136:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 8/1912:45 pm
BOS
- MCO
1 stop9h 29m
Frontier
Deal found 6/23![Frontier logo]()
$180
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Sun 8/1610:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/18![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 6/22. 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.
Mon 7/66:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 7/1410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/22![Frontier logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 6/22. 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.
Wed 7/226:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 7/2911:59 am
BOS
- MCO
1 stop6h 34m
Frontier
Deal found 6/22![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:24 pm
MCO
- BOS
1 stop14h 18m
Frontier
Mon 8/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/21![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Mon 7/66:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Thu 7/910:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/20![Frontier logo]()
$185
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 June 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 June 23, 2026.
This Delta deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:40 pm
MCO
- BOS
1 stop6h 37m
Delta
Sat 9/121:00 pm
BOS
- MCO
1 stop5h 48m
Delta
Deal found 6/23![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 6/22. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:30 pm
MCO
- BOS
Nonstop3h 13m
JetBlue
Wed 8/2612:44 pm
BOS
- MCO
1 stop7h 53m
JetBlue
Deal found 6/22![JetBlue logo]()
$248
This Southwest deal was found by Cheapflights users on 6/22. 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.
Sun 8/166:10 am
MCO
- BOS
1 stop7h 05m
Southwest
Sat 8/225:50 am
BOS
- MCO
1 stop4h 55m
Southwest
Deal found 6/22![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 6/19. 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.
Sat 9/121:55 pm
MCO
- BOS
1 stop5h 28m
Delta
Sun 9/207:00 am
BOS
- MCO
1 stop7h 44m
Delta
Deal found 6/19![Delta logo]()
$276
This Southwest deal was found by Cheapflights users on 6/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:00 am
MCO
- BOS
2 stops6h 50m
Southwest
Tue 9/225:25 am
BOS
- MCO
2 stops6h 50m
Southwest
Deal found 6/20![Southwest logo]()
$304
This JetBlue deal was found by Cheapflights users on 6/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:05 am
MCO
- BOS
1 stop7h 46m
JetBlue
Fri 7/38:31 pm
BOS
- MCO
Nonstop3h 11m
JetBlue
Deal found 6/19![JetBlue logo]()
$318
This Southwest deal was found by Cheapflights users on 6/22. 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.
Tue 7/289:45 am
MCO
- BOS
2 stops5h 55m
Southwest
Fri 7/315:45 am
BOS
- MCO
1 stop6h 05m
Southwest
Deal found 6/22![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:48 am
MCO
- BOS
1 stop6h 11m
Delta
Sun 8/168:20 pm
BOS
- MCO
Nonstop3h 14m
Delta
Deal found 6/18![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 6/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:05 am
MCO
- BOS
2 stops9h 15m
Southwest
Mon 7/610:25 pm
BOS
- MCO
1 stop10h 00m
Southwest
Deal found 6/20![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 6/20. 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.
Fri 7/108:43 am
MCO
- BOS
1 stop6h 16m
Delta
Sat 7/181:03 pm
BOS
- MCO
1 stop6h 02m
Delta
Deal found 6/20![Delta logo]()
$322
This Southwest deal was found by Cheapflights users on 6/22. 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.
Sat 7/49:25 am
MCO
- BOS
2 stops9h 30m
Southwest
Wed 7/810:30 am
BOS
- MCO
1 stop5h 40m
Southwest
Deal found 6/22![Southwest logo]()
$318
Last-minute flights from Kissimmee to BostonDiscover last-minute flight deals from Kissimmee to Boston. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Boston. Data last updated June 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 6/22. 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.
Mon 6/295:10 pm
MCO
- BOS
1 stop8h 17m
Frontier
Thu 7/1610:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/22![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 6/22. 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.
Mon 6/295:10 pm
MCO
- BOS
1 stop8h 17m
Frontier
Wed 7/1510:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/22![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 6/307:53 am
MCO
- BOS
1 stop17h 34m
Frontier
Wed 7/1510:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/23![Frontier logo]()
$261
This Frontier deal was found by Cheapflights users on 6/19. 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.
Tue 6/305:10 pm
MCO
- BOS
1 stop8h 17m
Frontier
Thu 7/910:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/19![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Tue 6/305:25 am
MCO
- BOS
1 stop20h 02m
Frontier
Sat 7/46:00 am
BOS
- MCO
1 stop13h 40m
Frontier
Deal found 6/19![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/25:10 pm
MCO
- BOS
1 stop8h 17m
Frontier
Sat 7/1110:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/18![Frontier logo]()
$227
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:10 pm
MCO
- BOS
1 stop8h 17m
Frontier
Thu 7/910:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/18![Frontier logo]()
$236
This CheapOair deal was found by Cheapflights users on 6/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:25 am
MCO
- BOS
1 stop27h 40m
Frontier
Sat 7/1110:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/19![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Fri 7/39:48 pm
MCO
- BOS
1 stop11h 02m
Multiple Airlines
Fri 7/108:41 am
BOS
- MCO
1 stop13h 44m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:10 pm
MCO
- BOS
1 stop16h 38m
Frontier
Tue 7/710:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/21![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 7/33:10 pm
MCO
- BOS
1 stop16h 38m
Frontier
Sun 7/510:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/20![Frontier logo]()
$271
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 June 23, 2026.
Search for one-way flight options from Kissimmee to Boston. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Tue 7/215:20 am
MCO
- BOS
1 stop5h 37m
Frontier
Deal found 6/19![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 6/21. 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 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 6/21![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 6/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:24 am
MCO
- BOS
1 stop6h 23m
Frontier
Deal found 6/21![Frontier logo]()
$104
This Priceline deal was found by Cheapflights users on 6/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:15 am
MCO
- BOS
1 stop5h 42m
Frontier
Deal found 6/22![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/22. 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.
Tue 7/285:24 pm
MCO
- BOS
1 stop14h 22m
Frontier
Deal found 6/22![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:25 am
MCO
- BOS
1 stop5h 25m
Frontier
Deal found 6/21![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Mon 8/35:24 pm
MCO
- BOS
1 stop17h 33m
Frontier
Deal found 6/20![Frontier logo]()
$108
This Southwest deal was found by Cheapflights users on 6/22. 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.
Sat 9/128:00 am
MCO
- BOS
1 stop6h 10m
Southwest
Deal found 6/22![Southwest logo]()
$109
This United Airlines deal was found by Cheapflights users on 6/23. 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 7/2910:52 am
MCO
- BOS
1 stop8h 38m
United Airlines
Deal found 6/23![United Airlines logo]()
$110
This Expedia deal was found by Cheapflights users on 6/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:24 am
MCO
- BOS
1 stop23h 08m
Frontier
Deal found 6/21![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 9/1110:53 am
MCO
- BOS
1 stop24h 52m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 7/317:21 am
MCO
- BOS
1 stop28h 40m
Frontier
Deal found 6/20![Frontier logo]()
$113
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (CheapOair) |
One-way from | $102 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $316 |
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 June 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
Tue 9/8
6:40 pm-1:17 am
1 stop6h 37m
Boston Logan Intl
Sat 9/12
1:00 pm-6:48 pm
1 stop5h 48m
$217
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Tue 8/25
6:30 pm-9:43 pm
Nonstop3h 13m
Boston Logan Intl
Wed 8/26
12:44 pm-8:37 pm
1 stop7h 53m
$248
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sun 8/16
6:10 am-1:15 pm
1 stop7h 05m
Boston Logan Intl
Sat 8/22
5:50 am-10:45 am
1 stop4h 55m
$252
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 9/12
1:55 pm-7:23 pm
1 stop5h 28m
Boston Logan Intl
Sun 9/20
7:00 am-2:44 pm
1 stop7h 44m
$276
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 9/19
9:00 am-3:50 pm
2 stops6h 50m
Boston Logan Intl
Tue 9/22
5:25 am-12:15 pm
2 stops6h 50m
$304
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Tue 7/28
9:45 am-3:40 pm
2 stops5h 55m
Boston Logan Intl
Fri 7/31
5:45 am-11:50 am
1 stop6h 05m
$308
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 7/4
6:05 am-3:20 pm
2 stops9h 15m
Boston Logan Intl
Mon 7/6
10:25 pm-8:25 am
1 stop10h 00m
$310
Quickest round-trip
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Thu 8/13
8:48 am-2:59 pm
1 stop6h 11m
Boston Logan Intl
Sun 8/16
8:20 pm-11:34 pm
Nonstop3h 14m
$312
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Fri 7/3
7:05 am-2:51 pm
1 stop7h 46m
Boston Logan Intl
Fri 7/3
8:31 pm-11:42 pm
Nonstop3h 11m
$318
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 7/4
9:25 am-6:55 pm
2 stops9h 30m
Boston Logan Intl
Wed 7/8
10:30 am-4:10 pm
1 stop5h 40m
$318
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 June 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 62% 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 June 23, 2026.
The most flights from K1S to BOS are scheduled on a Tuesday (51 on average). You will have fewer flight options on Thursday, 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?
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 June 20, 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 June 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
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
Brockton
Watertown
Hampton Beach
Seekonk
Cranston
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Dedham
Swansea
Old Orchard Beach
Lowell
Smithfield
Braintree
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Kissimmee to Boston
See prices for flight routes from nearby airports that may be better suited for you.
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 June 23, 2026.
Complete your trip
Complete your trip to Boston by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kissimmee to Boston by cabin class
Find flights from Kissimmee to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kissimmee and Boston flights
Browse other Kissimmee and Boston flight options. Last updated on June 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$40 | Average$160 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$67 | Average$188 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$112 | Average$271 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$281 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$120 | Average$324 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$181 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$184 | Average$286 | FlexibilityNo cancel fee | On-time69% |