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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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in July or January, booked 10 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap flight deals from Portland to Kissimmee

Keep the following information in mind while searching for Portland to Kissimmee flight deals. Data was last updated June 16, 2025.

Round-trip from

$156
(KAYAK)

One-way from

$79
(Breeze Airways)

Popular in

April

Cheapest in

July

Average price

$298
From Portland to Kissimmee
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One-way flight from Portland to Kissimmee
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Highest demand for flights based on searches. 3% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find 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 June 16, 2025.

This KAYAK deal was found by Cheapflights users on 6/14. 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.
Sat 7/126:58 pmPWM - MCO
Nonstop3h 38mFrontier
Sat 7/192:57 pmMCO - PWM
Nonstop3h 16mFrontier
Deal found 6/14$156
This Breeze Airways deal was found by Cheapflights users on 6/15. 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.
Fri 9/59:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Sat 9/1311:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 6/15$158
This eDestinos deal was found by Cheapflights users on 6/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/248:56 pmPWM - MCO
1 stop22h 08mAvelo Airlines
Sat 8/24:34 pmMCO - PWM
1 stop27h 38mAvelo Airlines
Deal found 6/15$172
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/15:30 amPWM - MCO
1 stop5h 10mSouthwest
Sat 7/59:10 amMCO - PWM
1 stop6h 00mSouthwest
Deal found 6/14$199
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Fri 7/44:02 pmPWM - MCO
1 stop5h 22mAmerican Airlines
Wed 7/92:45 pmMCO - PWM
1 stop5h 39mAmerican Airlines
Deal found 6/14$210
This Delta deal was found by Cheapflights users on 6/14. 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.
Wed 7/306:54 pmPWM - MCO
1 stop5h 21mDelta
Mon 8/46:15 amMCO - PWM
1 stop5h 51mDelta
Deal found 6/14$221
This Mytrip deal was found by Cheapflights users on 6/16. 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.
Sat 7/196:58 pmPWM - MCO
Nonstop3h 38mMultiple Airlines
Sat 7/267:30 pmMCO - PWM
1 stop16h 05mMultiple Airlines
Deal found 6/16$262
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Tue 7/17:15 pmPWM - MCO
1 stop5h 32mUnited Airlines
Sat 7/54:58 pmMCO - PWM
2 stops7h 01mUnited Airlines
Deal found 6/16$301
This JetBlue deal was found by Cheapflights users on 6/16. 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.
Thu 10/92:17 pmPWM - MCO
1 stop5h 20mJetBlue
Sun 10/127:25 amMCO - PWM
1 stop5h 57mJetBlue
Deal found 6/16$327

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 June 16, 2025.
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

Sat 7/12

6:58 pm-10:36 pm

Nonstop3h 38m

Orlando

Sat 7/19

2:57 pm-6:13 pm

Nonstop3h 16m

$156

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 9/5

9:46 am-1:20 pm

Nonstop3h 34m

Orlando

Sat 9/13

11:30 am-2:36 pm

Nonstop3h 06m

$158

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 7/24

8:56 pm-7:04 pm

1 stop22h 08m

Orlando

Sat 8/2

4:34 pm-8:12 pm

1 stop27h 38m

$172

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 7/1

5:30 am-10:40 am

1 stop5h 10m

Orlando

Sat 7/5

9:10 am-3:10 pm

1 stop6h 00m

$199

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 7/4

4:02 pm-9:24 pm

1 stop5h 22m

Orlando

Wed 7/9

2:45 pm-8:24 pm

1 stop5h 39m

$210

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 7/30

6:54 pm-12:15 am

1 stop5h 21m

Orlando

Mon 8/4

6:15 am-12:06 pm

1 stop5h 51m

$221

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 7/19

6:58 pm-10:36 pm

Nonstop3h 38m

Orlando

Sat 7/26

7:30 pm-11:35 am

1 stop16h 05m

$262

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 7/1

7:15 pm-12:47 am

1 stop5h 32m

Orlando

Sat 7/5

4:58 pm-11:59 pm

2 stops7h 01m

$301

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 10/9

2:17 pm-7:37 pm

1 stop5h 20m

Orlando

Sun 10/12

7:25 am-1:22 pm

1 stop5h 57m

$327

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 7/11

6:05 pm-9:27 pm

Nonstop3h 22m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 17 results
1
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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 June 13, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Kissimmee, you should look to book at least 10 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, May is the cheapest month in which you can book a flight from Portland, Maine to Kissimmee (average of $206). Flying from Portland, Maine to Kissimmee in November is currently the most expensive (average of $289). 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 June 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Kissimmee as you normally would.

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 June 15, 2025.

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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 June 16, 2025.
Read through reviews of airlines operating flights from Portland to Kissimmee, such as Breeze Airways, Southwest and Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
181 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
181 reviews
Breeze Airways
8.1
Very good
181 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,278 reviews
Breeze Airways
8.1
Very good
181 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,963 reviews
Breeze Airways
8.1
Very good
181 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Avelo Airlines
7.4
Good
Breeze Airways
8.1
Very good
181 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,801 reviews
Breeze Airways
8.1
Very good
181 reviews

Comfort

8.2

Food

6.7

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.3

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 $79. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Portland, Maine to Kissimmee for a low price.

  • What are the most reliable airlines from Portland, Maine to Kissimmee?

    No one likes to see their flight delayed. When booking a flight from Portland, Maine to Kissimmee consider choosing JetBlue (83%), Frontier (74%) or Breeze Airways (57%) as they are the most reliable in getting you off to your destination on time.

  • 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 $155, our data indicates the cheapest price to be $46. The most popular route (Portland - Orlando), is priced around $158.

  • 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, May is the cheapest month in which you can book a flight from Portland, Maine to Kissimmee (average of $206). Flying from Portland, Maine to Kissimmee in November is currently the most expensive (average of $289). 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.

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$155FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$85Average$232FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$93Average$239FlexibilityNo cancel feeOn-time62%
DeltaCheapest$165Average$326FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$178Average$375FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$399FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$206Average$419FlexibilityNo cancel feeOn-time69%

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