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Kissimmee

$116+ Cheap flights from Portland (PDX) 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 21 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 diciembre 12, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3012:47 pmPDX - MCO
1 stop13h 44mFrontier
jue. 1/86:00 amMCO - PDX
1 stop8h 15mFrontier
Deal found 12/10$233
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/2911:55 pmPDX - MCO
1 stop8h 10mUnited Airlines
mar. 1/66:30 amMCO - PDX
1 stop9h 12mUnited Airlines
Deal found 12/11$258
This Mytrip deal was found by Cheapflights users on 12/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/1212:55 pmPDX - MCO
1 stop23h 19mFrontier
mié. 1/149:00 amMCO - PDX
1 stop28h 33mFrontier
Deal found 12/9$276
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/175:30 pmPDX - MCO
1 stop9h 25mDelta
mié. 12/244:55 pmMCO - PDX
1 stop8h 58mDelta
Deal found 12/10$278
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/299:00 pmPDX - MCO
2 stops13h 05mSouthwest
mar. 1/66:55 amMCO - PDX
1 stop15h 20mSouthwest
Deal found 12/11$295
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/175:30 pmPDX - MCO
1 stop9h 25mDelta
dom. 12/216:55 pmMCO - PDX
1 stop8h 04mDelta
Deal found 12/10$297
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/1711:37 amPDX - MCO
1 stop8h 48mAmerican Airlines
sáb. 12/207:18 pmMCO - PDX
1 stop8h 41mAmerican Airlines
Deal found 12/10$309
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/3110:49 pmPDX - MCO
1 stop15h 57mAmerican Airlines
vie. 1/95:30 amMCO - PDX
1 stop10h 51mAmerican Airlines
Deal found 12/11$311
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/1011:59 pmPDX - MCO
1 stop7h 58mAmerican Airlines
mié. 1/147:14 amMCO - PDX
1 stop10h 34mAmerican Airlines
Deal found 12/10$336
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/173:55 pmPDX - MCO
2 stops10h 24mUnited Airlines
dom. 12/215:15 pmMCO - PDX
1 stop8h 44mUnited Airlines
Deal found 12/10$339
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/282:19 pmPDX - MCO
1 stop12h 31mFrontier
jue. 1/86:00 amMCO - PDX
1 stop8h 15mFrontier
Deal found 12/10$342
This Frontier deal was found by Cheapflights users on 12/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/313:59 pmPDX - MCO
1 stop12h 06mFrontier
sáb. 1/36:00 amMCO - PDX
1 stop8h 52mFrontier
Deal found 12/9$343

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 diciembre 12, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$202
(Kiwi.com)

One-way from

$116
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$492
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. 8% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 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 diciembre 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

PDX - MCO

PDXMCO

Portland

vie. 3/6

7:50 pm-6:39 am

1 stop7h 49m

Orlando

mar. 3/10

6:09 am-12:10 pm

1 stop9h 01m

$218

PortlandOrlando

PDX - MCO

PDXMCO

Portland

jue. 3/5

5:10 pm-6:39 am

1 stop10h 29m

Orlando

sáb. 3/7

6:00 am-12:02 pm

1 stop9h 02m

$218

PortlandOrlando

PDX - MCO

PDXMCO

Portland

jue. 3/5

7:35 pm-7:56 am

1 stop9h 21m

Orlando

lun. 3/9

8:55 am-8:58 pm

1 stop15h 03m

$222

PortlandOrlando

PDX - MCO

PDXMCO

Portland

mié. 1/21

6:20 am-8:05 pm

2 stops10h 45m

Orlando

mié. 1/28

4:05 pm-10:05 pm

1 stop9h 00m

$224

PortlandOrlando

PDX - MCO

PDXMCO

Portland

sáb. 1/24

7:10 am-7:40 pm

2 stops9h 30m

Orlando

mar. 1/27

9:10 am-3:40 pm

2 stops9h 30m

$229

PortlandOrlando

PDX - MCO

PDXMCO

Portland

dom. 1/4

9:00 pm-10:40 am

1 stop10h 40m

Orlando

vie. 1/9

9:10 am-3:40 pm

2 stops9h 30m

$230

PortlandOrlando

PDX - MCO

PDXMCO

Portland

mié. 1/28

6:20 am-8:35 pm

2 stops11h 15m

Orlando

vie. 1/30

6:55 am-7:15 pm

1 stop15h 20m

$230

PortlandOrlando

PDX - MCO

PDXMCO

Portland

sáb. 1/3

6:40 pm-10:50 am

1 stop13h 10m

Orlando

mié. 1/7

9:50 am-3:45 pm

1 stop8h 55m

$235

PortlandOrlando

PDX - MCO

PDXMCO

Portland

mié. 2/25

6:20 am-6:35 pm

2 stops9h 15m

Orlando

mar. 3/3

2:10 pm-9:20 pm

1 stop10h 10m

$243

PortlandOrlando

PDX - MCO

PDXMCO

Portland

mié. 2/25

3:55 pm-6:11 am

2 stops11h 16m

Orlando

mar. 3/10

6:09 am-12:10 pm

1 stop9h 01m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 24 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 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.

Booking 21 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Portland to Kissimmee?

Currently, January is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $138). Flying from Portland to Kissimmee in February is currently the most expensive (average of $206). 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 PDX 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 diciembre 12, 2025.

One of the essential ways to save on airfare from Portland to Kissimmee is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 41% on airfare.

What is the cheapest day to fly from Portland 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 to Kissimmee flight should consider departing on Thursday evenings 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 diciembre 12, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from Portland to Kissimmee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,432 reviews

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,432 reviews
Alaska Airlines
8.0
Very good
11,432 reviews

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,253 reviews
Alaska Airlines
8.0
Very good
11,432 reviews

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,008 reviews
Alaska Airlines
8.0
Very good
11,432 reviews

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,095 reviews
Alaska Airlines
8.0
Very good
11,432 reviews

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,050 reviews
Alaska Airlines
8.0
Very good
11,432 reviews

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Food

7.1

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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?

    If you book a flight to Kissimmee from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PDX) is located 6.0 mi from the center of Portland. There are 0 flights from Portland to Kissimmee per day from 9 different airlines.

  • How long is the flight from Portland to Kissimmee?

    For as low as $218, Delta can have you in Kissimmee from Portland in 7h 49m. Portland and Kissimmee are separated by a distance of 2529 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland to Kissimmee one-way?

    One-way options have recently been found by users for as low as $61 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $67 and Southwest from $98 one-way.

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

    Consider Sun Country Air (100%), Alaska Airlines (73%) or Hawaiian Airlines (73%) when booking your flight. These represent the most reliable airlines when flying from Portland to Kissimmee.

  • What are the cheapest flights from Portland to Kissimmee?

    While on average a flight from Portland to Kissimmee is generally $448, our data shows the cheapest flight currently is $177. When looking at the most popular route, (Portland - Orlando), you can expect to pay $179 for that flight.

  • 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 to Kissimmee?

    Currently, January is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $138). Flying from Portland to Kissimmee in February is currently the most expensive (average of $206). 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 9 airlines flying from Portland to Kissimmee

Discover the top 9 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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$181FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$248FlexibilityNo cancel feeOn-time62%
DeltaCheapest$195Average$367FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$393FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$206Average$468FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$206Average$413FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$228Average$453FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$236Average$386FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$276Average$484FlexibilityNo cancel feeOn-time85%

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