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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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$207
(Delta)

One-way from

$104
(Delta)

Popular in

June

Cheapest in

January

Average price

$426
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 ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/205:30 amPDX - MCO
1 stop8h 47mDelta
Fri 8/226:30 pmMCO - PDX
1 stop8h 22mDelta
Deal found 7/28$207
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/99:00 amPDX - MCO
2 stops9h 59mAmerican Airlines
Mon 9/155:40 pmMCO - PDX
1 stop9h 25mAmerican Airlines
Deal found 7/29$212
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/306:00 amPDX - MCO
2 stops9h 45mSouthwest
Sat 10/46:50 amMCO - PDX
1 stop15h 15mSouthwest
Deal found 7/28$218
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/267:52 pmPDX - MCO
2 stops16h 56mSpirit Airlines
Tue 9/26:00 amMCO - PDX
2 stops15h 57mSpirit Airlines
Deal found 7/29$233
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Sun 9/286:25 pmPDX - MCO
1 stop8h 08mUnited Airlines
Tue 9/303:55 pmMCO - PDX
1 stop8h 11mUnited Airlines
Deal found 7/29$235
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/113:10 pmPDX - MCO
1 stop14h 11mMultiple Airlines
Sat 8/308:59 pmMCO - PDX
1 stop30h 16mMultiple Airlines
Deal found 7/28$249
This Frontier deal was found by Cheapflights users on 7/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/206:51 amPDX - MCO
1 stop7h 24mFrontier
Sat 8/2311:07 amMCO - PDX
1 stop14h 32mFrontier
Deal found 7/28$258
This Hawaiian Airlines deal was found by Cheapflights users on 7/28. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2410:30 amPDX - MCO
Nonstop5h 49mHawaiian Airlines
Tue 9/305:50 pmMCO - PDX
Nonstop6h 00mHawaiian Airlines
Deal found 7/28$297

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 July 29, 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

Wed 8/20

5:30 am-5:17 pm

1 stop8h 47m

Orlando

Fri 8/22

6:30 pm-11:52 pm

1 stop8h 22m

$207

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 9/9

9:00 am-9:59 pm

2 stops9h 59m

Orlando

Mon 9/15

5:40 pm-12:05 am

1 stop9h 25m

$212

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 9/30

6:00 am-6:45 pm

2 stops9h 45m

Orlando

Sat 10/4

6:50 am-7:05 pm

1 stop15h 15m

$218

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 8/26

7:52 pm-3:48 pm

2 stops16h 56m

Orlando

Tue 9/2

6:00 am-6:57 pm

2 stops15h 57m

$233

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sun 9/28

6:25 pm-5:33 am

1 stop8h 08m

Orlando

Tue 9/30

3:55 pm-9:06 pm

1 stop8h 11m

$235

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 8/11

3:10 pm-8:21 am

1 stop14h 11m

Orlando

Sat 8/30

8:59 pm-12:15 am

1 stop30h 16m

$249

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 8/20

6:51 am-5:15 pm

1 stop7h 24m

Orlando

Sat 8/23

11:07 am-10:39 pm

1 stop14h 32m

$258

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 9/24

10:30 am-7:19 pm

Nonstop5h 49m

Orlando

Tue 9/30

5:50 pm-8:50 pm

Nonstop6h 00m

$297

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sat 9/6

10:15 am-12:12 am

1 stop10h 57m

$104

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 9/16

5:38 am-6:43 pm

2 stops10h 05m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 17 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 July 25, 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 $288). 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 July 29, 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 July 27, 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 July 29, 2025.

The most flights from PDX to K1S are scheduled on a Monday (2 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

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 July 29, 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
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,605 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.1

Comfort

7.8

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 American Airlines from $109 and Spirit Airlines from $119 one-way.

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

    Consider Sun Country Air (100%), Alaska Airlines (62%) or Hawaiian Airlines (62%) 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 $877, our data shows the cheapest flight currently is $168. When looking at the most popular route, (Portland - Orlando), you can expect to pay $207 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 $288). 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 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$227FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$226FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$201Average$494FlexibilityNo cancel feeOn-time71%
DeltaCheapest$205Average$389FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$206Average$444FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$228Average$453FlexibilityNo cancel feeOn-time83%
Alaska AirlinesCheapest$234Average$448FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$236Average$417FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$276Average$485FlexibilityNo cancel feeOn-time85%

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