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Kissimmee

$92+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or May, booked 23 days in advance, depart on a Tuesday or Monday and return on a Thursday

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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
PWM
-
MCO
1 stop5h 02m
American Airlines
Tue 3/245:55 pm
MCO
-
PWM
1 stop6h 00m
American Airlines
Deal found 1/27$177
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 5/1612:02 pm
PWM
-
MCO
Nonstop3h 25m
Breeze Airways
Fri 5/226:00 am
MCO
-
PWM
Nonstop3h 12m
Breeze Airways
Deal found 1/27$182
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 6/19:52 am
PWM
-
MCO
Nonstop3h 25m
Breeze Airways
Mon 6/86:00 am
MCO
-
PWM
Nonstop3h 12m
Breeze Airways
Deal found 1/29$183
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 5/259:52 am
PWM
-
MCO
Nonstop3h 25m
Breeze Airways
Fri 5/297:15 am
MCO
-
PWM
1 stop10h 18m
Breeze Airways
Deal found 1/27$186
This American Airlines deal was found by Cheapflights users on 1/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:00 am
PWM
-
MCO
1 stop5h 02m
American Airlines
Tue 3/37:00 am
MCO
-
PWM
1 stop5h 19m
American Airlines
Deal found 1/26$197
This Breeze Airways deal was found by Cheapflights users on 1/26. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:01 pm
PWM
-
MCO
1 stop6h 58m
Breeze Airways
Sat 6/208:10 am
MCO
-
PWM
Nonstop3h 12m
Breeze Airways
Deal found 1/26$198
This American Airlines deal was found by Cheapflights users on 1/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/71:18 pm
PWM
-
MCO
1 stop7h 58m
American Airlines
Wed 4/155:54 pm
MCO
-
PWM
1 stop5h 28m
American Airlines
Deal found 1/29$200
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 3/2311:29 am
PWM
-
MCO
1 stop11h 08m
Breeze Airways
Wed 3/257:10 am
MCO
-
PWM
Nonstop3h 07m
Breeze Airways
Deal found 1/27$202
This Mytrip deal was found by Cheapflights users on 1/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2311:29 am
PWM
-
MCO
1 stop4h 59m
Breeze Airways
Fri 3/276:00 am
MCO
-
PWM
Nonstop3h 07m
Breeze Airways
Deal found 1/27$205
This Priceline deal was found by Cheapflights users on 1/28. 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.
Mon 2/234:36 pm
PWM
-
MCO
Nonstop3h 29m
Multiple Airlines
Fri 2/276:00 am
MCO
-
PWM
Nonstop3h 07m
Multiple Airlines
Deal found 1/28$206
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 1/3111:02 am
PWM
-
MCO
Nonstop3h 34m
Breeze Airways
Mon 2/26:00 am
MCO
-
PWM
Nonstop3h 07m
Breeze Airways
Deal found 1/27$207
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/710:57 am
PWM
-
MCO
Nonstop3h 34m
Breeze Airways
Wed 2/117:10 am
MCO
-
PWM
Nonstop3h 07m
Breeze Airways
Deal found 1/27$208

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(American Airlines)

One-way from

$92
(American Airlines)

Popular in

October

Cheapest in

January

Average price

$220
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. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
Use the filters below to find and compare flights from Portland to Kissimmee that are best for you.

Fly from

Portland

Fly to

Kissimmee

Route

Depart

Return

Price

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 2/24

6:18 am-2:39 pm

1 stop8h 21m

Orlando

Wed 3/4

5:59 pm-11:20 pm

1 stop5h 21m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 2/25

6:00 am-1:31 pm

1 stop7h 31m

Orlando

Tue 3/3

7:00 am-3:14 pm

1 stop8h 14m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 3/24

6:00 am-11:02 am

1 stop5h 02m

Orlando

Tue 3/31

6:50 am-12:14 pm

1 stop5h 24m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 3/26

5:23 am-10:49 am

1 stop5h 26m

Orlando

Mon 3/30

3:54 pm-11:59 pm

1 stop8h 05m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 2/25

3:05 pm-12:43 am

2 stops9h 38m

Orlando

Wed 3/4

6:12 pm-11:20 pm

1 stop5h 08m

$222

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Mon 5/25

5:20 am-2:54 pm

2 stops9h 34m

Orlando

Fri 5/29

7:02 pm-11:50 pm

1 stop4h 48m

$242

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 4/23

5:11 pm-8:34 pm

Nonstop3h 23m

Orlando

Thu 4/30

7:00 am-1:23 pm

1 stop6h 23m

$250

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 2/18

3:05 pm-12:43 am

2 stops9h 38m

Orlando

Wed 2/25

7:10 am-3:14 pm

1 stop8h 04m

$254

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 2/27

2:25 pm-8:00 pm

1 stop5h 35m

Orlando

Fri 3/6

6:50 am-11:55 am

1 stop5h 05m

$257

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 3/14

5:20 pm-10:30 pm

1 stop5h 10m

Orlando

Fri 3/20

6:50 am-11:55 am

1 stop5h 05m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 22 results
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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

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 January 23, 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, February is the cheapest month in which you can book a flight from Portland, Maine to Kissimmee (average of $36). Flying from Portland, Maine to Kissimmee in October is currently the most expensive (average of $87). 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 January 29, 2026.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 31% 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 January 24, 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. Wednesday 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 January 29, 2026.
See what other customers who have flown with Breeze Airways, Southwest, and American Airlines 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
263 reviews

Crew

8.7

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Crew

8.7

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,267 reviews
Breeze Airways
8.2
Very good
263 reviews

Crew

8.7

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,206 reviews
Breeze Airways
8.2
Very good
263 reviews

Crew

8.7

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
JetBlue
7.2
Good
2,892 reviews
Breeze Airways
8.2
Very good
263 reviews

Crew

8.7

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,056 reviews
Breeze Airways
8.2
Very good
263 reviews

Crew

8.7

Boarding

8.3

Comfort

8.2

Entertainment

6.6

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 7 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 5h 02m. Delta provides one of the quickest options available for as low as $217. 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 Frontier, with whom users have recently found tickets for as low as $47. However, be on the lookout for offers from Breeze Airways and American Airlines, 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 $210, our data indicates the cheapest price to be $74. The most popular route (Portland - Orlando), is priced around $177.

  • 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.

  • What is the cheapest month to book a flight from Portland, Maine to Kissimmee?

    Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Kissimmee (average of $36). Flying from Portland, Maine to Kissimmee in October is currently the most expensive (average of $87). 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.

See more FAQs

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$47Average$137FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$84Average$244FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$91Average$226FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$108Average$314FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$395FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$182Average$381FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$428FlexibilityNo cancel feeOn-time71%

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