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Kissimmee

$78+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MCO
Mar 15 — Mar 221
Sat 3/15
Sat 3/22
1 adult, Economy
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The best prices from Portland to Kissimmee are usually found in July or January, booked 15 days in advance, depart on a Tuesday or Wednesday 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 March 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$96
(Cheapflightsfares)

One-way from

$78
(Kiwi.com)

Popular in

April

Cheapest in

July

Average price

$211
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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Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 10, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 3/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2210:08 amPWM - MCO
Nonstop3h 39mFrontier
Sat 3/296:00 amMCO - PWM
Nonstop3h 08mFrontier
Deal found 3/10$96
This Orbitz deal was found by Cheapflights users on 3/9. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1112:38 pmPWM - MCO
Nonstop3h 22mMultiple Airlines
Sat 6/1412:42 pmMCO - PWM
Nonstop3h 09mMultiple Airlines
Deal found 3/9$125
This Priceline deal was found by Cheapflights users on 3/9. 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 6/97:18 pmPWM - MCO
Nonstop3h 22mBreeze Airways
Wed 6/118:45 amMCO - PWM
Nonstop3h 08mBreeze Airways
Deal found 3/9$142
This JetBlue deal was found by Cheapflights users on 3/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2411:50 amPWM - MCO
Nonstop3h 32mJetBlue
Sat 3/298:55 amMCO - PWM
Nonstop2h 58mJetBlue
Deal found 3/10$167
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/295:45 pmPWM - MCO
1 stop5h 25mSouthwest
Wed 4/27:00 amMCO - PWM
1 stop5h 45mSouthwest
Deal found 3/10$187
This American Airlines deal was found by Cheapflights users on 3/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/295:20 pmPWM - MCO
2 stops7h 21mAmerican Airlines
Wed 4/29:32 amMCO - PWM
1 stop6h 09mAmerican Airlines
Deal found 3/10$192
This United Airlines deal was found by Cheapflights users on 3/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/173:55 pmPWM - MCO
2 stops8h 35mUnited Airlines
Fri 3/215:50 pmMCO - PWM
1 stop5h 25mUnited Airlines
Deal found 3/10$212
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/61:52 pmPWM - MCO
1 stop6h 53mDelta
Fri 5/96:00 amMCO - PWM
1 stop7h 50mDelta
Deal found 3/10$217

Find flights from Portland to Kissimmee within your budget

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 March 10, 2025.

Fly from

Portland

Fly to

Kissimmee

Route

Depart

Return

Price

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 3/22

10:08 am-1:47 pm

Nonstop3h 39m

Orlando

Sat 3/29

6:00 am-9:08 am

Nonstop3h 08m

$96

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 5/3

9:29 pm-12:51 am

Nonstop3h 22m

Orlando

Mon 6/16

3:30 pm-6:38 pm

Nonstop3h 08m

$129

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 6/6

7:18 pm-10:40 pm

Nonstop3h 22m

Orlando

Mon 6/9

3:30 pm-6:38 pm

Nonstop3h 08m

$152

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Mon 3/24

11:50 am-3:22 pm

Nonstop3h 32m

Orlando

Sat 3/29

8:55 am-11:53 am

Nonstop2h 58m

$167

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 3/29

5:45 pm-11:10 pm

1 stop5h 25m

Orlando

Wed 4/2

7:00 am-12:45 pm

1 stop5h 45m

$187

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sat 3/29

5:20 pm-12:41 am

2 stops7h 21m

Orlando

Wed 4/2

9:32 am-3:41 pm

1 stop6h 09m

$192

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Mon 3/17

3:55 pm-12:30 am

2 stops8h 35m

Orlando

Fri 3/21

5:50 pm-11:15 pm

1 stop5h 25m

$212

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Tue 5/6

1:52 pm-8:45 pm

1 stop6h 53m

Orlando

Fri 5/9

6:00 am-1:50 pm

1 stop7h 50m

$217

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Fri 6/6

7:18 pm-10:40 pm

Nonstop3h 22m

$78

PortlandOrlando

PWM - MCO

PWMMCO

Portland

Sun 4/6

10:08 am-1:33 pm

Nonstop3h 25m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

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.

Travel insights for flights from Portland to Kissimmee

Get recent, data-driven insights about flights from Portland to Kissimmee including ideal travel times, pricing trends, and more.

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 March 7, 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, 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 March 10, 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 9, 2025.

Travelers seeking maximum savings on their Portland, Maine to Kissimmee flight should consider departing on Monday 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.

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 March 10, 2025.
Read through reviews of airlines operating flights from Portland to Kissimmee, such as Southwest, Delta and Breeze Airways. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,300 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
7,973 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Breeze Airways
8.0
Very good
155 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,631 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

JetBlue
7.3
Good
2,962 reviews
Southwest
8.1
Very good
4,300 reviews

Comfort

8.1

Entertainment

7.6

Boarding

8.2

Food

7.1

Crew

8.7

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $78. However, be on the lookout for offers from Frontier and JetBlue, 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 (85%), Frontier (70%) or Southwest (50%) 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 $167, our data indicates the cheapest price to be $59. The most popular route (Portland - Orlando), is priced around $113.

  • 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 March 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$183FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$79Average$237FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$93Average$282FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$185Average$420FlexibilityNo cancel feeOn-time71%
DeltaCheapest$187Average$364FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$232Average$434FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$247Average$431FlexibilityNo cancel feeOn-time63%
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