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Kissimmee

$104+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 32 days in advance, depart on a Wednesday or Thursday and return on a Thursday

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 June 12, 2025.

Round-trip from

$207
(Delta)

One-way from

$104
(Delta)

Popular in

June

Cheapest in

January

Average price

$492
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. 8% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/147:05 pmPDX - MCO
1 stop7h 33mDelta
Mon 8/46:32 pmMCO - PDX
1 stop8h 56mDelta
Deal found 6/9$207
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/96:30 amPDX - MCO
2 stops10h 30mSouthwest
Sat 11/157:05 amMCO - PDX
1 stop8h 10mSouthwest
Deal found 6/9$212
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Tue 9/165:38 amPDX - MCO
1 stop9h 38mAmerican Airlines
Sat 9/206:30 amMCO - PDX
1 stop8h 44mAmerican Airlines
Deal found 6/11$220
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/145:00 amPDX - MCO
1 stop7h 59mUnited Airlines
Mon 8/185:03 pmMCO - PDX
1 stop8h 30mUnited Airlines
Deal found 6/10$239
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/112:12 pmPDX - MCO
2 stops29h 12mMultiple Airlines
Thu 7/318:25 pmMCO - PDX
1 stop22h 22mMultiple Airlines
Deal found 6/10$244
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
Mon 7/213:10 pmPDX - MCO
1 stop14h 11mSpirit Airlines
Sun 7/279:28 pmMCO - PDX
1 stop14h 50mSpirit Airlines
Deal found 6/12$247
This Hawaiian Airlines deal was found by Cheapflights users on 6/11. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2210:30 amPDX - MCO
Nonstop5h 44mHawaiian Airlines
Thu 9/255:50 pmMCO - PDX
Nonstop6h 00mHawaiian Airlines
Deal found 6/11$297
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/610:31 amPDX - MCO
Nonstop5h 28mAlaska Airlines
Sat 10/115:48 pmMCO - PDX
Nonstop6h 02mAlaska Airlines
Deal found 6/10$318
This Sun Country Air deal was found by Cheapflights users on 6/9. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:16 pmPDX - MCO
1 stop19h 22mSun Country Air
Sun 10/126:15 pmMCO - PDX
1 stop26h 07mSun Country Air
Deal found 6/9$335
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/246:53 pmPDX - MCO
1 stop15h 53mFrontier
Wed 6/258:59 pmMCO - PDX
1 stop16h 19mFrontier
Deal found 6/12$360

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 June 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

Mon 7/14

7:05 pm-5:38 am

1 stop7h 33m

Orlando

Wed 7/30

12:10 pm-7:03 pm

1 stop9h 53m

$207

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sun 11/9

6:30 am-8:00 pm

2 stops10h 30m

Orlando

Sat 11/15

7:05 am-12:15 pm

1 stop8h 10m

$212

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 9/16

5:38 am-6:16 pm

1 stop9h 38m

Orlando

Sat 9/20

6:30 am-12:14 pm

1 stop8h 44m

$220

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Thu 8/14

5:00 am-3:59 pm

1 stop7h 59m

Orlando

Mon 8/18

5:03 pm-10:33 pm

1 stop8h 30m

$239

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 7/1

12:12 pm-8:24 pm

2 stops29h 12m

Orlando

Thu 7/31

8:25 pm-3:47 pm

1 stop22h 22m

$244

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 7/21

3:10 pm-8:21 am

1 stop14h 11m

Orlando

Sun 7/27

9:28 pm-9:18 am

1 stop14h 50m

$247

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 9/22

10:30 am-7:14 pm

Nonstop5h 44m

Orlando

Thu 9/25

5:50 pm-8:50 pm

Nonstop6h 00m

$297

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 10/6

10:31 am-6:59 pm

Nonstop5h 28m

Orlando

Sat 10/11

5:48 pm-8:50 pm

Nonstop6h 02m

$318

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sun 10/5

6:16 pm-4:38 pm

1 stop19h 22m

Orlando

Sun 10/12

6:15 pm-5:22 pm

1 stop26h 07m

$335

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 6/24

6:53 pm-1:46 pm

1 stop15h 53m

Orlando

Wed 6/25

8:59 pm-10:18 am

1 stop16h 19m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 20 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 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 June 9, 2025.

Booking 32 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, May is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $206). Flying from Portland 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 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 June 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland to Kissimmee as you normally would.

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 June 8, 2025.

Travelers seeking maximum savings on their Portland to Kissimmee flight should consider departing on Sunday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Portland to Kissimmee

Explore weekly flight availability from Portland to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from PDX to K1S are scheduled on a Thursday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 June 12, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 is 1 flight from Portland to Kissimmee per day from 9 different airlines.

  • 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 $104 on Delta. Other airlines that offer cheap prices include Southwest from $109 and American Airlines from $130 one-way.

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

    Consider Sun Country Air (100%), Alaska Airlines (77%) or Hawaiian Airlines (77%) 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 $393, our data shows the cheapest flight currently is $183. When looking at the most popular route, (Portland - Orlando), you can expect to pay $181 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, May is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $206). Flying from Portland 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 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$230FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$221FlexibilityNo cancel feeOn-time62%
DeltaCheapest$205Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$496FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$212Average$473FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$235Average$443FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$241Average$417FlexibilityNo cancel feeOn-time69%
Sun Country AirCheapest$271Average$453FlexibilityNo cancel feeOn-time83%
Hawaiian AirlinesCheapest$304Average$498FlexibilityNo cancel feeOn-time85%

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