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Kissimmee

$83+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or March, booked 15 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 December 12, 2025.

This Super.com deal was found by Cheapflights users on 12/11. 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.
Mon 12/159:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Wed 12/177:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 12/11$156
This Breeze Airways deal was found by Cheapflights users on 12/11. 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 12/1311:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Fri 12/196:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 12/11$173
This Breeze Airways deal was found by Cheapflights users on 12/10. 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 12/1311:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Mon 12/156:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 12/10$178
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/1311:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Sat 12/207:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 12/10$205
This Breeze Airways deal was found by Cheapflights users on 12/11. 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 12/129:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Fri 12/196:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 12/11$248
This Breeze Airways deal was found by Cheapflights users on 12/11. 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 12/3111:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Mon 1/57:30 amMCO - PWM
1 stop9h 55mBreeze Airways
Deal found 12/11$250
This Super.com deal was found by Cheapflights users on 12/10. 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.
Wed 12/2411:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Sat 12/277:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 12/10$266

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 December 12, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$152
(Kiwi.com)

One-way from

$83
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$257
Provider with most accurate pricing for Boston Logan Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-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. 6% potential increase in price ($18 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 December 2025
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 December 12, 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

Fri 1/30

11:29 am-11:07 pm

1 stop11h 38m

Orlando

Sat 2/7

7:10 am-10:17 am

Nonstop3h 07m

$168

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sun 1/18

12:45 pm-6:35 pm

1 stop5h 50m

Orlando

Thu 1/22

10:15 am-2:55 pm

1 stop4h 40m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 3/3

5:45 am-1:30 pm

1 stop7h 45m

Orlando

Wed 3/25

3:55 pm-11:05 pm

1 stop7h 10m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 1/31

5:10 am-12:50 pm

1 stop7h 40m

Orlando

Tue 2/3

9:20 am-2:55 pm

1 stop5h 35m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 1/21

12:45 pm-6:35 pm

1 stop5h 50m

Orlando

Sun 1/25

6:15 am-12:25 pm

1 stop6h 10m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 2/4

12:45 pm-6:35 pm

1 stop5h 50m

Orlando

Wed 2/11

4:10 pm-10:15 pm

1 stop6h 05m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sun 1/18

3:30 pm-8:40 pm

1 stop5h 10m

Orlando

Wed 1/21

7:00 am-12:10 pm

1 stop5h 10m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 1/31

12:35 pm-6:40 pm

1 stop6h 05m

Orlando

Wed 2/4

10:15 am-2:55 pm

1 stop4h 40m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 1/21

3:45 pm-7:14 pm

Nonstop3h 29m

Orlando

Wed 1/28

10:55 am-1:58 pm

Nonstop3h 03m

$187

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 1/10

11:02 am-2:36 pm

Nonstop3h 34m

Orlando

Wed 1/14

7:15 am-10:22 am

Nonstop3h 07m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 23 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 December 5, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Kissimmee, you should look to book at least 15 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 $32). Flying from Portland, Maine to Kissimmee in October is currently the most expensive (average of $84). 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 December 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 45% 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 December 6, 2025.

Travelers seeking maximum savings on their Portland, Maine to Kissimmee flight should consider departing on Friday at noon when fares are most often at their lowest. Sunday mornings 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 December 12, 2025.
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
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Breeze Airways
8.2
Very good
244 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Southwest
7.9
Good
4,253 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
American Airlines
7.2
Good
11,050 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
JetBlue
7.2
Good
2,899 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.
Frontier
5.8
Fair
3,084 reviews
Breeze Airways
8.2
Very good
244 reviews

Entertainment

6.6

Food

6.7

Boarding

8.4

Comfort

8.2

Crew

8.8

Overall

8.2

Reviews

1 / 15
8.0
Excellent

Lyle,Dec 2025

BDL - RSW

Seating was comfortable, crew excellent, no food or entertainment offered.

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 50m. Breeze Airways provides one of the quickest options available for as low as $183. 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 $196, our data indicates the cheapest price to be $106. The most popular route (Portland - Orlando), is priced around $152.

  • 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 $32). Flying from Portland, Maine to Kissimmee in October is currently the most expensive (average of $84). 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$150FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$99Average$275FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$104Average$227FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$138Average$322FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$182Average$394FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$418FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$200Average$389FlexibilityNo cancel feeOn-time69%

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