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Kissimmee

$54+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
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 Thursday and return on a Wednesday

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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$106
(Cheapflightsfares)

One-way from

$54
(Frontier)

Popular in

April

Cheapest in

July

Average price

$207
Provider with most accurate pricing for Portland-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Portland-Orlando (ORL) flights.
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From Portland to Kissimmee
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One-way flight from Portland to Kissimmee
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/159:29 pmPWM - MCO
Nonstop3h 22mFrontier
Mon 5/195:22 pmMCO - PWM
Nonstop3h 18mFrontier
Deal found 5/1$106
This CheapOair deal was found by Cheapflights users on 5/1. 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 9/199:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Sat 9/2711:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 5/1$139
This Southwest deal was found by Cheapflights users on 4/30. 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 5/282:20 pmPWM - MCO
1 stop6h 20mSouthwest
Wed 6/43:50 pmMCO - PWM
1 stop6h 40mSouthwest
Deal found 4/30$151
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/216:00 amPWM - MCO
1 stop5h 01mAmerican Airlines
Wed 5/284:24 pmMCO - PWM
1 stop6h 42mAmerican Airlines
Deal found 4/30$159
This Priceline deal was found by Cheapflights users on 4/30. 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.
Sat 5/314:57 pmPWM - MCO
Nonstop3h 21mMultiple Airlines
Fri 6/63:30 pmMCO - PWM
Nonstop3h 08mMultiple Airlines
Deal found 4/30$172
This JetBlue deal was found by Cheapflights users on 4/30. 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 11/103:45 pmPWM - MCO
Nonstop3h 10mJetBlue
Mon 11/1711:45 amMCO - PWM
Nonstop3h 01mJetBlue
Deal found 4/30$213
This Delta deal was found by Cheapflights users on 4/30. 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 6/126:56 pmPWM - MCO
1 stop6h 23mDelta
Wed 6/253:52 pmMCO - PWM
1 stop7h 38mDelta
Deal found 4/30$217
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/137:09 pmPWM - MCO
1 stop5h 36mUnited Airlines
Fri 6/204:51 pmMCO - PWM
1 stop6h 37mUnited Airlines
Deal found 4/29$255

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 May 1, 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

Thu 5/15

9:29 pm-12:51 am

Nonstop3h 22m

Orlando

Mon 5/19

5:22 pm-8:40 pm

Nonstop3h 18m

$106

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 9/19

9:46 am-1:20 pm

Nonstop3h 34m

Orlando

Sat 9/27

11:30 am-2:36 pm

Nonstop3h 06m

$139

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 5/28

2:20 pm-8:40 pm

1 stop6h 20m

Orlando

Wed 6/4

3:50 pm-10:30 pm

1 stop6h 40m

$151

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 5/21

6:00 am-11:01 am

1 stop5h 01m

Orlando

Wed 5/28

4:24 pm-11:06 pm

1 stop6h 42m

$159

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 5/31

4:57 pm-8:18 pm

Nonstop3h 21m

Orlando

Fri 6/6

3:30 pm-6:38 pm

Nonstop3h 08m

$172

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Thu 6/12

6:56 pm-1:19 am

1 stop6h 23m

Orlando

Wed 6/25

3:52 pm-11:30 pm

1 stop7h 38m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 6/6

3:35 pm-10:30 pm

1 stop6h 55m

Orlando

Thu 6/12

6:45 am-1:23 pm

1 stop6h 38m

$221

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 8/20

10:05 am-2:57 pm

1 stop4h 52m

Orlando

Sat 8/23

11:43 am-7:29 pm

2 stops7h 46m

$226

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 6/28

7:25 pm-10:57 pm

Nonstop3h 32m

$54

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Mon 8/11

6:05 pm-9:27 pm

Nonstop3h 22m

$70

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 16 results
1
2

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 April 25, 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 May 1, 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 March 30, 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 May 1, 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
160 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Overall

8.1

Food

6.7

Comfort

8.2

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
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Overall

8.1

Food

6.7

Comfort

8.2

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
4,293 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Overall

8.1

Food

6.7

Comfort

8.2

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
7,934 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Overall

8.1

Food

6.7

Comfort

8.2

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
8,696 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Overall

8.1

Food

6.7

Comfort

8.2

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!
JetBlue
7.3
Good
2,923 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Entertainment

6.6

Crew

8.8

Overall

8.1

Food

6.7

Comfort

8.2

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 Frontier, with whom users have recently found tickets for as low as $54. However, be on the lookout for offers from Breeze Airways and Southwest, 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 Frontier (84%), JetBlue (77%) or Southwest (67%) 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 $146, our data indicates the cheapest price to be $46. The most popular route (Portland - Orlando), is priced around $129.

  • 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.

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$190FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$81Average$234FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$93Average$276FlexibilityNo cancel feeOn-time62%
DeltaCheapest$165Average$343FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$180Average$406FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$208Average$420FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$418FlexibilityNo cancel feeOn-time63%

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