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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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or August, booked 32 days in advance, depart on a Tuesday or Wednesday 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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(American Airlines)

One-way from

$104
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$442
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. 2% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 26, 2025.

This Delta deal was found by Cheapflights users on 3/25. 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 9/155:10 pmPDX - MCO
1 stop10h 39mDelta
Tue 9/236:30 pmMCO - PDX
1 stop8h 22mDelta
Deal found 3/25$207
This Southwest deal was found by Cheapflights users on 3/25. 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.
Thu 8/146:10 amPDX - MCO
1 stop11h 45mSouthwest
Sun 8/177:10 amMCO - PDX
1 stop9h 30mSouthwest
Deal found 3/25$212
This Priceline deal was found by Cheapflights users on 3/24. 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 5/105:40 pmPDX - MCO
1 stop8h 45mSpirit Airlines
Tue 5/1310:25 amMCO - PDX
1 stop9h 20mSpirit Airlines
Deal found 3/24$215
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Thu 5/111:02 amPDX - MCO
2 stops32h 49mMultiple Airlines
Tue 5/67:30 amMCO - PDX
2 stops32h 10mMultiple Airlines
Deal found 3/25$250
This Frontier deal was found by Cheapflights users on 3/25. 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.
Thu 4/106:40 amPDX - MCO
1 stop7h 34mFrontier
Sun 4/139:16 pmMCO - PDX
1 stop13h 55mFrontier
Deal found 3/25$278
This American Airlines deal was found by Cheapflights users on 3/25. 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 11/1512:07 pmPDX - MCO
1 stop9h 11mAmerican Airlines
Sat 11/225:00 pmMCO - PDX
1 stop8h 52mAmerican Airlines
Deal found 3/25$293
This United Airlines deal was found by Cheapflights users on 3/25. 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 5/1911:59 pmPDX - MCO
1 stop10h 09mUnited Airlines
Fri 5/235:12 pmMCO - PDX
1 stop8h 23mUnited Airlines
Deal found 3/25$314
This Alaska Airlines deal was found by Cheapflights users on 3/25. 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.
Tue 9/1610:30 amPDX - MCO
Nonstop5h 44mAlaska Airlines
Thu 9/255:50 pmMCO - PDX
Nonstop6h 00mAlaska Airlines
Deal found 3/25$348
This Hawaiian Airlines deal was found by Cheapflights users on 3/25. 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.
Sun 9/217:36 pmPDX - MCO
1 stop9h 08mHawaiian Airlines
Sat 9/275:50 pmMCO - PDX
Nonstop6h 00mHawaiian Airlines
Deal found 3/25$378

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 March 26, 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

Sat 4/19

5:31 am-4:30 pm

1 stop7h 59m

Orlando

Tue 4/22

3:00 pm-11:02 pm

1 stop11h 02m

$207

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sat 5/10

5:40 pm-5:25 am

1 stop8h 45m

Orlando

Tue 5/13

10:25 am-4:45 pm

1 stop9h 20m

$215

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 4/18

7:59 pm-6:47 am

1 stop7h 48m

Orlando

Mon 4/21

6:30 pm-11:56 pm

1 stop8h 26m

$233

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sun 4/13

6:00 am-7:55 pm

1 stop10h 55m

Orlando

Tue 4/15

4:50 pm-11:10 pm

1 stop9h 20m

$245

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Thu 5/1

11:02 am-10:51 pm

2 stops32h 49m

Orlando

Tue 5/6

7:30 am-12:40 pm

2 stops32h 10m

$250

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Thu 4/10

6:40 am-5:14 pm

1 stop7h 34m

Orlando

Sun 4/13

9:16 pm-8:11 am

1 stop13h 55m

$278

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 5/19

11:59 pm-1:08 pm

1 stop10h 09m

Orlando

Fri 5/23

5:12 pm-10:35 pm

1 stop8h 23m

$314

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 4/15

7:04 am-3:34 pm

Nonstop5h 30m

Orlando

Sat 4/19

8:08 pm-11:34 pm

Nonstop6h 26m

$368

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 5/30

10:00 am-6:37 pm

Nonstop5h 37m

Orlando

Sat 6/7

6:05 pm-11:38 pm

1 stop8h 33m

$378

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 5/30

10:24 pm-10:57 am

1 stop9h 33m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 19 results
1
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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 March 21, 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 March 26, 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 March 23, 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.

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 26, 2025.
See what other customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Crew

8.6

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.
Alaska Airlines
8.0
Very good
9,789 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Crew

8.6

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.
Hawaiian Airlines
7.9
Good
2,331 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Crew

8.6

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
8,608 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Boarding

8.2

Crew

8.6

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?

    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 American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $118 and Southwest from $149 one-way.

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

    Consider Alaska Airlines (92%), Hawaiian Airlines (92%) or LATAM Airlines (89%) 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 $442, our data shows the cheapest flight currently is $194. 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 $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 March 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$209FlexibilityNo cancel feeOn-time65%
FrontierCheapest$123Average$223FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$142Average$398FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$206Average$382FlexibilityNo cancel feeOn-time71%
DeltaCheapest$206Average$416FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$235Average$436FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$236Average$429FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$310Average$493FlexibilityNo cancel feeOn-time63%
Hawaiian AirlinesCheapest$368Average$538FlexibilityNo cancel feeOn-time85%
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