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Kissimmee

$79+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 23 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to Kissimmee

Cheapest flights from Portland to Kissimmee
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 July 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/235:09 pm
PWM
-
MCO
1 stop6h 33m
Breeze Airways
Wed 9/307:10 am
MCO
-
PWM
1 stop9h 24m
Breeze Airways
Deal found 7/27$179
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/55:01 pm
PWM
-
MCO
1 stop6h 43m
Breeze Airways
Sat 9/127:20 am
MCO
-
PWM
Nonstop3h 08m
Breeze Airways
Deal found 7/27$193
This Breeze Airways deal was found by Cheapflights users on 7/27. 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 9/305:09 pm
PWM
-
MCO
1 stop6h 33m
Breeze Airways
Mon 10/56:00 am
MCO
-
PWM
Nonstop3h 08m
Breeze Airways
Deal found 7/27$205
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/119:48 am
PWM
-
MCO
Nonstop3h 34m
Breeze Airways
Wed 9/167:20 am
MCO
-
PWM
Nonstop3h 08m
Breeze Airways
Deal found 7/27$208
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 9/155:09 pm
PWM
-
MCO
1 stop18h 54m
Multiple Airlines
Mon 9/216:00 am
MCO
-
PWM
Nonstop3h 08m
Multiple Airlines
Deal found 7/27$214
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Fri 9/49:52 am
PWM
-
MCO
Nonstop3h 25m
Breeze Airways
Wed 9/97:20 am
MCO
-
PWM
Nonstop3h 08m
Breeze Airways
Deal found 7/23$217
This Breeze Airways deal was found by Cheapflights users on 7/27. 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 9/911:08 am
PWM
-
MCO
Nonstop3h 34m
Breeze Airways
Sat 9/197:20 am
MCO
-
PWM
Nonstop3h 08m
Breeze Airways
Deal found 7/27$218
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 9/911:08 am
PWM
-
MCO
Nonstop3h 34m
Breeze Airways
Wed 9/167:20 am
MCO
-
PWM
Nonstop3h 08m
Breeze Airways
Deal found 7/26$219
This Breeze Airways deal was found by Cheapflights users on 7/24. 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 9/211:07 am
PWM
-
MCO
Nonstop3h 25m
Breeze Airways
Sat 9/57:15 am
MCO
-
PWM
Nonstop3h 12m
Breeze Airways
Deal found 7/24$223
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Mon 8/317:00 am
PWM
-
MCO
2 stops13h 00m
Multiple Airlines
Sat 9/127:20 am
MCO
-
PWM
Nonstop3h 08m
Multiple Airlines
Deal found 7/23$224

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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$179
(Kiwi.com)

One-way from

$79
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$298
Provider with most accurate pricing for Portland-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Orlando (ORL) flights.
Search Deals
From Portland to Kissimmee
Search Deals
One-way flight from Portland to Kissimmee
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 28, 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

Price

Cheapest round-trip

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 10/23

11:25 am-6:48 pm

1 stop7h 23m

Orlando

Mon 11/2

3:51 pm-12:10 am

1 stop8h 19m

$277

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 9/24

6:30 am-2:43 pm

1 stop8h 13m

Orlando

Wed 9/30

5:40 pm-11:28 pm

1 stop5h 48m

$277

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sun 9/20

6:02 am-12:45 pm

1 stop6h 43m

Orlando

Fri 9/25

3:41 pm-11:56 pm

1 stop8h 15m

$277
Quickest round-trip

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 9/30

5:29 pm-10:49 pm

1 stop5h 20m

Orlando

Sat 10/3

7:00 am-11:56 am

1 stop4h 56m

$277

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 9/24

6:00 am-1:57 pm

2 stops7h 57m

Orlando

Wed 9/30

7:21 pm-11:59 pm

1 stop4h 38m

$282

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 10/23

1:05 pm-9:05 pm

2 stops8h 00m

Orlando

Tue 10/27

12:00 pm-8:30 pm

2 stops8h 30m

$287

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 9/24

10:30 am-7:55 pm

2 stops9h 25m

Orlando

Tue 9/29

2:55 pm-9:15 pm

1 stop6h 20m

$288

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 8/25

2:53 pm-11:19 pm

1 stop8h 26m

Orlando

Tue 9/1

3:40 pm-11:13 pm

1 stop7h 33m

$297

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 8/19

5:45 am-12:15 pm

2 stops6h 30m

Orlando

Wed 8/26

4:10 pm-9:10 pm

1 stop5h 00m

$302

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 9/23

10:30 am-6:00 pm

2 stops7h 30m

Orlando

Sun 9/27

6:15 pm-10:55 pm

1 stop4h 40m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 21 resultsSorted by cheapest first
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3

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.
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

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 July 28, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 34% 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 $213 and $358 in September.
The cheapest round-trip price found within the last 5 days was $179 on Breeze Airways (Sep 23-Sep 30).

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 July 25, 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. Saturday afternoons 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 July 28, 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.
Breeze Airways
8.2
Very good
302 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
302 reviews
Breeze Airways
8.2
Very good
302 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Southwest
8.0
Very good
4,228 reviews
Breeze Airways
8.2
Very good
302 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Delta
7.8
Good
8,482 reviews
Breeze Airways
8.2
Very good
302 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,839 reviews
Breeze Airways
8.2
Very good
302 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
JetBlue
7.1
Good
3,025 reviews
Breeze Airways
8.2
Very good
302 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Entertainment

6.7

Food

6.7

Overall

8.2

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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.

  • What airport do you fly from for flights from Portland to Kissimmee?

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Kissimmee. You should not have trouble finding flights to Kissimmee from Portland; the airport handles an average of 0 outbound flights to Kissimmee per day. You should also have plenty of airline options to choose from since 6 airlines have flights from the Portland airport to Kissimmee. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

  • How long is the flight from Portland, Maine to Kissimmee?

    A quick flight from Portland, Maine to Kissimmee can take about 7h 23m. Delta provides one of the quickest options available for as low as $277. There are 1214 mi between Portland, Maine and Kissimmee. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Portland, Maine to Kissimmee one-way?

    The cheapest airline one-way is Breeze Airways, with whom users have recently found tickets for as low as $77. However, be on the lookout for offers from American Airlines and Southwest, as they are both options that can get you from Portland, Maine to Kissimmee for a low price.

  • What are the cheapest flights from Portland, Maine to Kissimmee?

    Looking for the cheapest flight from Portland, Maine to Kissimmee? While on average our users pay $266, our data indicates the cheapest price to be $132. The most popular route (Portland - Orlando), is priced around $157.

  • Can I find deals for flights from Portland to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Portland to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Kissimmee.

  • Can I find deals for business class flights from Portland to Kissimmee?

    Yes. Cheapflights offers flight deals from Portland to Kissimmee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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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 2,558,603 searches. Data last updated July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$99Average$265FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$99Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$110Average$355FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$153Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$183Average$404FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$198Average$480FlexibilityNo cancel feeOn-time71%

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