$118+ Cheap flights from Portland, ME (PWM) to Kissimmee, FL
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
May 8 — May 151
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Kissimmee with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in August or January, booked 23 days in advance, depart on a Tuesday or Sunday and return on a Thursday
Cheap flight deals from Portland to Kissimmee
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to KissimmeeExplore the most affordable flight options available from Portland to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 8, 2026.
Explore the most affordable flight options available from Portland to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 8, 2026.
This Delta deal was found by Cheapflights users on 4/6. 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 5/196:25 am
PWM
- MCO
1 stop8h 09m
Delta
Tue 5/266:00 am
MCO
- PWM
1 stop7h 58m
Delta
Deal found 4/6![Delta logo]()
$217
This Breeze Airways deal was found by Cheapflights users on 4/5. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:48 am
PWM
- MCO
Nonstop3h 34m
Breeze Airways
Sat 10/37:00 am
MCO
- PWM
1 stop9h 24m
Breeze Airways
Deal found 4/5![Breeze Airways logo]()
$218
This Booking.com deal was found by Cheapflights users on 4/4. 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.
Wed 7/2911:07 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Mon 8/36:00 am
MCO
- PWM
Nonstop3h 12m
Breeze Airways
Deal found 4/4![Breeze Airways logo]()
$219
This Expedia deal was found by Cheapflights users on 4/4. 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.
Sat 9/265:09 pm
PWM
- MCO
1 stop6h 33m
Breeze Airways
Sat 10/36:00 am
MCO
- PWM
Nonstop3h 08m
Breeze Airways
Deal found 4/4![Breeze Airways logo]()
$220
This Breeze Airways deal was found by Cheapflights users on 4/4. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:09 pm
PWM
- MCO
1 stop6h 33m
Breeze Airways
Fri 9/187:30 am
MCO
- PWM
1 stop9h 20m
Breeze Airways
Deal found 4/4![Breeze Airways logo]()
$221
This Southwest deal was found by Cheapflights users on 4/5. 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 6/64:55 pm
PWM
- MCO
1 stop5h 10m
Southwest
Tue 6/93:10 pm
MCO
- PWM
2 stops7h 45m
Southwest
Deal found 4/5![Southwest logo]()
$222
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:52 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Mon 6/16:00 am
MCO
- PWM
Nonstop3h 12m
Breeze Airways
Deal found 4/6![Breeze Airways logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/135:01 pm
PWM
- MCO
1 stop6h 58m
Multiple Airlines
Wed 5/207:25 am
MCO
- PWM
1 stop8h 51m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:57 am
PWM
- MCO
Nonstop3h 34m
Multiple Airlines
Wed 5/67:25 am
MCO
- PWM
1 stop8h 51m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:30 am
PWM
- MCO
1 stop5h 28m
Delta
Wed 5/66:07 pm
MCO
- PWM
1 stop6h 39m
Delta
Deal found 4/7![Delta logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:01 pm
PWM
- MCO
1 stop6h 58m
Multiple Airlines
Mon 6/84:46 pm
MCO
- PWM
1 stop21h 45m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$228
Best flights from Portland to KissimmeeDiscover carefully curated flight deals from Portland to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 8, 2026.
Discover carefully curated flight deals from Portland to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 8, 2026.
This Delta deal was found by Cheapflights users on 4/5. 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 5/192:38 pm
PWM
- MCO
1 stop8h 33m
Delta
Tue 5/266:00 am
MCO
- PWM
1 stop7h 58m
Delta
Deal found 4/5![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 4/3. 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 5/2912:45 pm
PWM
- MCO
2 stops7h 10m
Southwest
Mon 6/16:05 pm
MCO
- PWM
1 stop5h 20m
Southwest
Deal found 4/3![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/113:39 pm
PWM
- MCO
1 stop6h 19m
United Airlines
Fri 5/155:10 pm
MCO
- PWM
1 stop6h 13m
United Airlines
Deal found 4/6![United Airlines logo]()
$249
This Breeze Airways deal was found by Cheapflights users on 4/7. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:01 pm
PWM
- MCO
1 stop6h 58m
Breeze Airways
Mon 5/116:00 am
MCO
- PWM
Nonstop3h 12m
Breeze Airways
Deal found 4/7![Breeze Airways logo]()
$317
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:10 am
PWM
- MCO
2 stops9h 25m
Southwest
Sat 5/93:45 pm
MCO
- PWM
2 stops7h 25m
Southwest
Deal found 4/3![Southwest logo]()
$317
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:15 am
PWM
- MCO
2 stops9h 28m
United Airlines
Mon 6/13:05 pm
MCO
- PWM
2 stops8h 25m
United Airlines
Deal found 4/3![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 4/4. 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 4/252:51 pm
PWM
- MCO
1 stop8h 12m
Delta
Sat 5/27:23 am
MCO
- PWM
1 stop6h 48m
Delta
Deal found 4/4![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/34:20 pm
PWM
- MCO
1 stop6h 30m
Southwest
Thu 5/76:05 pm
MCO
- PWM
1 stop5h 20m
Southwest
Deal found 4/3![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 4/7. 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 5/82:05 pm
PWM
- MCO
1 stop7h 44m
Delta
Mon 5/113:50 pm
MCO
- PWM
1 stop7h 28m
Delta
Deal found 4/7![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 4/6. 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 4/254:35 pm
PWM
- MCO
1 stop5h 20m
Southwest
Wed 4/297:20 am
MCO
- PWM
1 stop5h 00m
Southwest
Deal found 4/6![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 4/4. 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 4/254:35 pm
PWM
- MCO
1 stop5h 20m
Southwest
Sat 5/22:25 pm
MCO
- PWM
2 stops9h 00m
Southwest
Deal found 4/4![Southwest logo]()
$357
Last-minute flights from Portland to KissimmeeDiscover last-minute flight deals from Portland to Kissimmee. Data last updated April 8, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Kissimmee. Data last updated April 8, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 4/3. 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.
Mon 4/139:47 am
PWM
- MCO
Nonstop3h 34m
Breeze Airways
Fri 4/176:00 am
MCO
- PWM
Nonstop3h 07m
Breeze Airways
Deal found 4/3![Breeze Airways logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:47 am
PWM
- MCO
Nonstop3h 34m
Multiple Airlines
Tue 5/59:44 pm
MCO
- PWM
2 stops18h 32m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/2910:57 am
PWM
- MCO
Nonstop3h 34m
Multiple Airlines
Wed 5/65:10 pm
MCO
- PWM
2 stops26h 06m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 4/3. 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 5/12:50 pm
PWM
- MCO
1 stop5h 30m
Southwest
Fri 5/82:00 pm
MCO
- PWM
2 stops9h 25m
Southwest
Deal found 4/3![Southwest logo]()
$222
This Booking.com deal was found by Cheapflights users on 4/7. 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.
Fri 5/111:29 am
PWM
- MCO
1 stop11h 08m
Breeze Airways
Sat 5/96:00 am
MCO
- PWM
Nonstop3h 12m
Breeze Airways
Deal found 4/7![Breeze Airways logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:57 am
PWM
- MCO
Nonstop3h 34m
Multiple Airlines
Wed 5/67:25 am
MCO
- PWM
1 stop8h 51m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:30 am
PWM
- MCO
1 stop5h 28m
Delta
Wed 5/66:07 pm
MCO
- PWM
1 stop6h 39m
Delta
Deal found 4/7![Delta logo]()
$227
This Booking.com deal was found by Cheapflights users on 4/4. 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.
Mon 5/411:29 am
PWM
- MCO
1 stop4h 59m
Breeze Airways
Mon 5/116:00 am
MCO
- PWM
Nonstop3h 12m
Breeze Airways
Deal found 4/4![Breeze Airways logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 5/135:01 pm
PWM
- MCO
1 stop6h 58m
Multiple Airlines
Wed 5/207:25 am
MCO
- PWM
1 stop8h 51m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 4/6. 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 5/196:25 am
PWM
- MCO
1 stop8h 09m
Delta
Tue 5/266:00 am
MCO
- PWM
1 stop7h 58m
Delta
Deal found 4/6![Delta logo]()
$217
This CheapOair deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:52 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Mon 6/16:00 am
MCO
- PWM
Nonstop3h 12m
Breeze Airways
Deal found 4/6![Breeze Airways logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:01 pm
PWM
- MCO
1 stop6h 58m
Multiple Airlines
Mon 6/84:46 pm
MCO
- PWM
1 stop21h 45m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$228
One-way flights from Portland to KissimmeeSearch for one-way flight options from Portland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 8, 2026.
Search for one-way flight options from Portland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/77:56 pm
PWM
- MCO
1 stop27h 32m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$118
This Delta deal was found by Cheapflights users on 4/7. 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.
Sun 5/36:30 am
PWM
- MCO
1 stop5h 28m
Delta
Deal found 4/7![Delta logo]()
$119
This KAYAK deal was found by Cheapflights users on 4/7. 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.
Sun 4/265:41 pm
PWM
- MCO
Nonstop3h 23m
JetBlue
Deal found 4/7![JetBlue logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 7/249:52 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Deal found 4/4![Breeze Airways logo]()
$123
This Delta deal was found by Cheapflights users on 4/6. 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 4/242:51 pm
PWM
- MCO
1 stop8h 12m
Delta
Deal found 4/6![Delta logo]()
$124
This Booking.com deal was found by Cheapflights users on 4/7. 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.
Mon 5/189:52 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Deal found 4/7![Breeze Airways logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 7/15:01 pm
PWM
- MCO
1 stop6h 58m
Breeze Airways
Deal found 4/3![Breeze Airways logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 10/29:48 am
PWM
- MCO
Nonstop3h 34m
Breeze Airways
Deal found 4/5![Breeze Airways logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 7/45:01 pm
PWM
- MCO
1 stop6h 58m
Breeze Airways
Deal found 4/7![Breeze Airways logo]()
$130
This Booking.com deal was found by Cheapflights users on 4/5. 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.
Sat 5/99:52 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Deal found 4/5![Breeze Airways logo]()
$133
This CheapOair deal was found by Cheapflights users on 4/3. 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 5/89:52 am
PWM
- MCO
Nonstop3h 25m
Breeze Airways
Deal found 4/3![Breeze Airways logo]()
$134
Find flight deals from Portland to Kissimmee
Keep the following information in mind while searching for Portland to Kissimmee flight deals. Data was last updated April 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Delta) |
One-way from | $118 (Kiwi.com) |
Popular in | April |
Cheapest in | August |
Average price | $318 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Kissimmee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 8, 2026.
Use the filters below to find and compare flights from Portland to Kissimmee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Tue 5/19
2:38 pm-11:11 pm
1 stop8h 33m
Orlando
Tue 5/26
6:00 am-1:58 pm
1 stop7h 58m
$217
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Fri 5/29
12:45 pm-7:55 pm
2 stops7h 10m
Orlando
Mon 6/1
6:05 pm-11:25 pm
1 stop5h 20m
$222
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Mon 5/11
3:39 pm-9:58 pm
1 stop6h 19m
Orlando
Fri 5/15
5:10 pm-11:23 pm
1 stop6h 13m
$249
Quickest round-trip
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Wed 5/6
5:01 pm-11:59 pm
1 stop6h 58m
Orlando
Mon 5/11
6:00 am-9:12 am
Nonstop3h 12m
$317
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Wed 5/6
6:10 am-3:35 pm
2 stops9h 25m
Orlando
Sat 5/9
3:45 pm-11:10 pm
2 stops7h 25m
$317
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Fri 5/29
5:15 am-2:43 pm
2 stops9h 28m
Orlando
Mon 6/1
3:05 pm-11:30 pm
2 stops8h 25m
$317
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Sun 5/3
4:20 pm-10:50 pm
1 stop6h 30m
Orlando
Thu 5/7
6:05 pm-11:25 pm
1 stop5h 20m
$317
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Sat 4/25
2:51 pm-11:03 pm
1 stop8h 12m
Orlando
Sat 5/2
7:23 am-2:11 pm
1 stop6h 48m
$328
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Sat 4/25
4:35 pm-9:55 pm
1 stop5h 20m
Orlando
Wed 4/29
7:20 am-12:20 pm
1 stop5h 00m
$332
PortlandOrlando
PWM - MCO
PWMMCO
Portland
Fri 5/8
2:05 pm-9:49 pm
1 stop7h 44m
Orlando
Mon 5/11
3:50 pm-11:18 pm
1 stop7h 28m
$348
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from Portland to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Portland with our price prediction graph.
PWM-MCO
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Kissimmee
PWM-K1S
PWM-MCO
How far ahead should I book a flight from Portland, Maine to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from Portland to Kissimmee. Price data was last updated on April 3, 2026.
To ensure you get the cheapest price possible for a flight from Portland, Maine to Kissimmee, you should look to book at least 23 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Portland, Maine to Kissimmee?
Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Kissimmee (average of $59). Flying from Portland, Maine to Kissimmee in March is currently the most expensive (average of $117). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PWM to K1S?
Find hourly flight availability from Portland to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 8, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 30% on flights from Portland, Maine to Kissimmee by exploring options for tickets in the evening.
What is the cheapest day to fly from Portland, Maine to Kissimmee?
Use this chart to determine the cheapest time to fly round-trip from Portland to Kissimmee. Price data was last updated on April 4, 2026.
Travelers seeking maximum savings on their Portland, Maine to Kissimmee flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
How much does it cost to fly round-trip from Portland, Maine to Kissimmee?
Reviews of airlines servicing Kissimmee
Get insights into the airlines that provide service to Kissimmee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kissimmee. Reviews last updated April 8, 2026.
See what other customers who have flown with Breeze Airways,Southwest, andDelta from Portland to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Overall
8.1
Comfort
8.2
Crew
8.7
Entertainment
6.6
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Overall
8.1
Comfort
8.2
Crew
8.7
Entertainment
6.6
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Overall
8.1
Comfort
8.2
Crew
8.7
Entertainment
6.6
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Overall
8.1
Comfort
8.2
Crew
8.7
Entertainment
6.6
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Overall
8.1
Comfort
8.2
Crew
8.7
Entertainment
6.6
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Food
6.6
Overall
8.1
Comfort
8.2
Crew
8.7
Entertainment
6.6
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Portland to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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 Portland to Kissimmee
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Kissimmee by cabin class
Find flights from Portland to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Portland and Kissimmee flights
Browse other Portland and Kissimmee flight options. Last updated on April 8, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on April 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Portland to Kissimmee flights
Consider these flights traveling from Portland to Kissimmee.
Top 7 airlines flying from Portland to Kissimmee
Discover the top 7 airlines that operate flights from Portland to Kissimmee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$46 | Average$104 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$272 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$96 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$337 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$387 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$182 | Average$394 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$187 | Average$411 | FlexibilityNo cancel fee | On-time71% |