$93+ Cheap flights from Portland, ME (PWM) to Kissimmee, FL
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Oct 11 — Oct 181
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 January or September, booked 14 days in advance, depart on a Tuesday or Wednesday and return on a Sunday
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 September 11, 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 September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/45:09 pm -
1 stop6h 16m
Fri 11/136:00 am -
Nonstop3h 08m
Deal found 9/10![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/45:09 pm -
1 stop6h 16m
Wed 11/186:00 am -
Nonstop3h 08m
Deal found 9/9![Multiple Airlines logo]()
$205
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 11/145:09 pm -
1 stop6h 33m
Tue 11/178:00 am -
1 stop8h 24m
Deal found 9/10![Breeze Airways logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Fri 11/139:48 am -
Nonstop3h 34m
Wed 11/186:00 am -
Nonstop3h 08m
Deal found 9/7![Breeze Airways logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Fri 11/139:48 am -
Nonstop3h 34m
Sat 11/146:00 am -
Nonstop3h 08m
Deal found 9/7![Breeze Airways logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/115:09 pm -
1 stop6h 16m
Wed 11/256:00 am -
Nonstop3h 08m
Deal found 9/9![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/45:09 pm -
1 stop6h 33m
Fri 11/136:00 am -
Nonstop3h 08m
Deal found 9/7![Breeze Airways logo]()
$211
This Breeze Airways deal was found by Cheapflights users on 9/7. 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.
Mon 11/309:48 am -
Nonstop3h 34m
Fri 12/46:00 am -
Nonstop3h 08m
Deal found 9/7![Breeze Airways logo]()
$213
This Breeze Airways deal was found by Cheapflights users on 9/9. 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 11/115:09 pm -
1 stop6h 33m
Wed 11/186:00 am -
Nonstop3h 08m
Deal found 9/9![Breeze Airways logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/45:09 pm -
1 stop6h 16m
Wed 11/117:15 am -
1 stop9h 09m
Deal found 9/10![Multiple Airlines logo]()
$216
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 10/285:09 pm -
1 stop6h 33m
Tue 11/38:00 am -
1 stop8h 24m
Deal found 9/10![Breeze Airways logo]()
$217
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 September 11, 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 September 11, 2026.
This Breeze Airways deal was found by Cheapflights users on 9/7. 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.
Sat 1/169:48 am -
Nonstop3h 34m
Sat 1/236:00 am -
Nonstop3h 08m
Deal found 9/7![Breeze Airways logo]()
$208
This Delta deal was found by Cheapflights users on 9/10. 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 11/126:00 am -
1 stop8h 22m
Mon 11/165:04 pm -
1 stop7h 15m
Deal found 9/10![Delta logo]()
$277
This Southwest deal was found by Cheapflights users on 9/9. 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 10/233:25 pm -
1 stop6h 00m
Tue 10/276:10 am -
2 stops9h 20m
Deal found 9/9![Southwest logo]()
$282
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 10/285:09 pm -
1 stop6h 33m
Tue 11/38:00 am -
1 stop8h 24m
Deal found 9/10![Breeze Airways logo]()
$217
This Breeze Airways deal was found by Cheapflights users on 9/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:48 am -
Nonstop3h 34m
Wed 11/116:00 am -
Nonstop3h 08m
Deal found 9/6![Breeze Airways logo]()
$238
This Southwest deal was found by Cheapflights users on 9/5. 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.
Wed 12/212:45 pm -
2 stops7h 15m
Mon 12/77:35 am -
1 stop4h 35m
Deal found 9/5![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:40 am -
2 stops8h 20m
Tue 11/310:25 am -
2 stops11h 20m
Deal found 9/8![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:03 pm -
1 stop6h 28m
Mon 11/235:04 pm -
1 stop7h 15m
Deal found 9/8![Delta logo]()
$360
This Breeze Airways deal was found by Cheapflights users on 9/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:09 pm -
1 stop6h 33m
Mon 10/196:00 am -
Nonstop3h 08m
Deal found 9/6![Breeze Airways logo]()
$315
This Breeze Airways deal was found by Cheapflights users on 9/7. 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 10/75:09 pm -
1 stop6h 33m
Mon 10/126:00 am -
Nonstop3h 08m
Deal found 9/7![Breeze Airways logo]()
$337
This Breeze Airways deal was found by Cheapflights users on 9/10. 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.
Mon 10/199:48 am -
Nonstop3h 34m
Fri 10/236:00 am -
Nonstop3h 08m
Deal found 9/10![Breeze Airways logo]()
$348
Last-minute flights from Portland to KissimmeeDiscover last-minute flight deals from Portland to Kissimmee. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Kissimmee. Data last updated September 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/237:00 am -
2 stops16h 42m
Sat 10/36:00 am -
Nonstop3h 08m
Deal found 9/9![Breeze Airways logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/237:00 am -
2 stops16h 42m
Wed 9/307:05 am -
1 stop9h 19m
Deal found 9/9![Breeze Airways logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/248:14 pm -
Nonstop3h 30m
Tue 9/298:00 am -
1 stop8h 24m
Deal found 9/10![Breeze Airways logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 9/267:00 am -
2 stops16h 42m
Tue 9/298:00 am -
1 stop8h 24m
Deal found 9/7![Breeze Airways logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/267:00 am -
2 stops16h 42m
Sat 10/36:00 am -
Nonstop3h 08m
Deal found 9/9![Breeze Airways logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/267:00 am -
2 stops16h 42m
Wed 9/307:05 am -
1 stop9h 19m
Deal found 9/9![Breeze Airways logo]()
$236
This JetBlue deal was found by Cheapflights users on 9/9. 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.
Mon 10/56:00 am -
1 stop7h 06m
Tue 10/65:00 pm -
1 stop6h 54m
Deal found 9/9![JetBlue logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/249:48 am -
Nonstop3h 34m
Wed 10/286:00 am -
Nonstop3h 08m
Deal found 9/10![Breeze Airways logo]()
$232
This Breeze Airways deal was found by Cheapflights users on 9/8. 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 10/245:09 pm -
1 stop6h 33m
Tue 11/38:00 am -
1 stop8h 24m
Deal found 9/8![Breeze Airways logo]()
$235
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 10/285:09 pm -
1 stop6h 33m
Tue 11/38:00 am -
1 stop8h 24m
Deal found 9/10![Breeze Airways logo]()
$217
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 September 11, 2026.
Search for one-way flight options from Portland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 10/315:09 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Wed 10/285:09 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/99:48 am -
Nonstop3h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Breeze Airways logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/75:09 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$110
This Breeze Airways deal was found by Cheapflights users on 9/10. 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 12/912:28 pm -
1 stop11h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$114
This Super.com deal was found by Cheapflights users on 9/10. 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 10/245:09 pm -
1 stop6h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Breeze Airways logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/45:09 pm -
1 stop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/115:09 pm -
1 stop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$124
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (Kiwi.com) |
One-way from | $93 (Breeze Airways) |
Popular in | August |
Cheapest in | January |
Average price | $274 |
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 7,457,451 searches. Data last updated September 11, 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
Quickest round-trip
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Sat 1/16
9:48 am-1:22 pm
Nonstop3h 34m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Fri 11/13
4:03 pm-10:31 pm
1 stop6h 28m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Fri 11/13
9:48 am-1:22 pm
Nonstop3h 34m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Sat 10/31
7:20 am-5:35 pm
2 stops10h 15m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Tue 12/8
5:15 am-2:00 pm
2 stops8h 45m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Thu 12/3
11:40 am-6:52 pm
1 stop7h 12m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Wed 9/16
6:00 am-1:05 pm
1 stop7h 05m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$161
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Sat 10/3
7:25 pm-12:59 am
1 stop5h 34m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Wed 10/21
5:40 am-2:00 pm
2 stops8h 20m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
PortlandOrlando
PWM Portland - MCO Orlando
PWMMCO
Portland
Sun 11/8
5:50 am-2:43 pm
2 stops8h 53m
Orlando
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$189
Showing 1-10 of 22 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
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 September 11, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 51% on flights from Portland, Maine to Kissimmee by exploring options for tickets in the evening.
How much does it cost to fly round-trip from Portland, Maine to Kissimmee?
Airfare is below average for this route at the moment.
Portland, Maine to Kissimmee flights typically cost between $216 and $327 in February.The cheapest round-trip price found within the last 5 days was $203 on Breeze Airways (Feb 6-Feb 13).
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 September 5, 2026.
Travelers seeking maximum savings on their Portland, Maine to Kissimmee flight should consider departing on Wednesday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 September 11, 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.
Boarding
8.4
Overall
8.2
Crew
8.8
Food
6.8
Comfort
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.4
Overall
8.2
Crew
8.8
Food
6.8
Comfort
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.4
Overall
8.2
Crew
8.8
Food
6.8
Comfort
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.4
Overall
8.2
Crew
8.8
Food
6.8
Comfort
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.4
Overall
8.2
Crew
8.8
Food
6.8
Comfort
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.4
Overall
8.2
Crew
8.8
Food
6.8
Comfort
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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Portland and Kissimmee flights
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Top 6 airlines flying from Portland to Kissimmee
Discover the top 6 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$269 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$121 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$355 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$398 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$183 | Average$405 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$199 | Average$480 | FlexibilityNo cancel fee | On-time71% |