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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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or March, booked 17 days in advance, depart on a Monday or Tuesday and return on a Tuesday

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 October 28, 2025.

This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline 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
Mon 12/156:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/26$147
This Breeze Airways deal was found by Cheapflights users on 10/27. 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.
Fri 12/129:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Wed 12/177:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/27$153
This Priceline deal was found by Cheapflights users on 10/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Mon 12/86:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/26$157
This Breeze Airways deal was found by Cheapflights users on 10/27. 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.
Mon 12/159:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Mon 12/226:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/27$158
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sat 12/611:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Wed 12/107:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/26$163
This Breeze Airways deal was found by Cheapflights users on 10/27. 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 11/1911:21 amPWM - MCO
1 stop5h 33mBreeze Airways
Wed 11/267:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/27$164
This Priceline deal was found by Cheapflights users on 10/28. 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.
Wed 12/244:20 pmPWM - MCO
Nonstop3h 32mJetBlue
Wed 12/3112:23 pmMCO - PWM
Nonstop3h 02mJetBlue
Deal found 10/28$167
This Breeze Airways deal was found by Cheapflights users on 10/26. 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.
Mon 11/109:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Sat 11/157:30 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/26$168
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 11/109:46 amPWM - MCO
Nonstop3h 34mBreeze Airways
Fri 11/146:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/26$174
This Southwest deal was found by Cheapflights users on 10/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/103:00 pmPWM - MCO
1 stop7h 20mSouthwest
Fri 11/146:30 amMCO - PWM
1 stop4h 40mSouthwest
Deal found 10/26$177
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1911:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Fri 11/216:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/28$178
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/1311:16 amPWM - MCO
Nonstop3h 34mBreeze Airways
Mon 12/226:00 amMCO - PWM
Nonstop3h 06mBreeze Airways
Deal found 10/27$179

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$143
(Breeze Airways)

One-way from

$79
(Breeze Airways)

Popular in

October

Cheapest in

January

Average price

$310
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. 4% potential increase in price ($11 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 October 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 October 28, 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 1/23

9:47 am-1:21 pm

Nonstop3h 34m

Orlando

Mon 1/26

6:00 am-9:07 am

Nonstop3h 07m

$153

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 11/19

11:16 am-2:50 pm

Nonstop3h 34m

Orlando

Wed 11/26

7:30 am-10:36 am

Nonstop3h 06m

$168

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Mon 1/26

11:29 am-4:28 pm

1 stop4h 59m

Orlando

Fri 1/30

7:15 am-4:26 pm

1 stop9h 11m

$176

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 12/17

4:35 pm-8:00 pm

Nonstop3h 25m

Orlando

Wed 12/31

12:23 pm-3:25 pm

Nonstop3h 02m

$177

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 1/17

3:56 pm-9:57 pm

1 stop6h 01m

Orlando

Wed 1/21

7:13 pm-11:43 pm

1 stop4h 30m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 1/17

3:20 pm-9:40 pm

1 stop6h 20m

Orlando

Sat 1/24

6:40 am-12:05 pm

1 stop5h 25m

$183

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Mon 12/22

4:20 pm-7:52 pm

Nonstop3h 32m

Orlando

Wed 12/31

12:23 pm-3:25 pm

Nonstop3h 02m

$203

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 11/8

11:16 am-2:50 pm

Nonstop3h 34m

Orlando

Sat 11/15

7:30 am-10:36 am

Nonstop3h 06m

$208

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Wed 11/19

6:35 am-11:54 am

1 stop5h 19m

Orlando

Thu 11/20

8:23 am-1:50 pm

1 stop5h 27m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 10/31

9:46 am-1:20 pm

Nonstop3h 34m

Orlando

Mon 11/3

6:00 am-9:06 am

Nonstop3h 06m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Kissimmee, you should look to book at least 17 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 October 28, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 48% 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 October 26, 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 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 October 28, 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
8.1
Very good
220 reviews

Boarding

8.3

Comfort

8.1

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
220 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Comfort

8.1

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Southwest
8.0
Very good
4,240 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Comfort

8.1

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,033 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Comfort

8.1

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
JetBlue
7.2
Good
2,908 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Comfort

8.1

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Frontier
5.8
Fair
3,124 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Comfort

8.1

Crew

8.7

Entertainment

6.6

Overall

8.1

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 1 outbound flight 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 3h 25m. Breeze Airways provides one of the quickest options available for as low as $177. 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 flights from Portland, Maine to Kissimmee?

    Looking for the cheapest flight from Portland, Maine to Kissimmee? While on average our users pay $207, our data indicates the cheapest price to be $91. The most popular route (Portland - Orlando), is priced around $143.

  • 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$152FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$96Average$226FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$99Average$286FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$318FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$183Average$397FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$413FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$200Average$387FlexibilityNo cancel feeOn-time69%

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