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Kissimmee

$108+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 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 September 11, 2025.

Round-trip from

$207
(American Airlines)

One-way from

$108
(Delta)

Popular in

June

Cheapest in

January

Average price

$338
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. 9% potential increase in price ($41 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 September 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/11. 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 9/306:07 amPDX - MCO
1 stop9h 22mAmerican Airlines
Fri 10/36:04 pmMCO - PDX
1 stop8h 55mAmerican Airlines
Deal found 9/11$207
This Delta deal was found by Cheapflights users on 9/9. 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.
Sat 11/85:00 pmPDX - MCO
1 stop9h 55mDelta
Sat 11/1512:44 pmMCO - PDX
1 stop11h 03mDelta
Deal found 9/9$209
This Southwest deal was found by Cheapflights users on 9/11. 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.
Fri 10/313:25 pmPDX - MCO
1 stop10h 50mSouthwest
Wed 11/59:55 amMCO - PDX
2 stops15h 05mSouthwest
Deal found 9/11$211
This Southwest deal was found by Cheapflights users on 9/11. 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.
Tue 10/216:30 pmPDX - MCO
1 stop7h 45mSouthwest
Wed 10/222:50 pmMCO - PDX
2 stops9h 25mSouthwest
Deal found 9/11$212
This Southwest deal was found by Cheapflights users on 9/10. 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 9/279:50 amPDX - MCO
1 stop7h 25mSouthwest
Wed 10/13:00 pmMCO - PDX
1 stop10h 45mSouthwest
Deal found 9/10$213
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:59 pmPDX - MCO
1 stop8h 44mDelta
Mon 12/156:20 pmMCO - PDX
1 stop8h 55mDelta
Deal found 9/11$215
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 11/511:43 amPDX - MCO
1 stop8h 41mAmerican Airlines
Wed 11/123:01 pmMCO - PDX
1 stop11h 30mAmerican Airlines
Deal found 9/10$217
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2212:43 pmPDX - MCO
1 stop14h 21mMultiple Airlines
Mon 10/278:41 amMCO - PDX
2 stops30h 15mMultiple Airlines
Deal found 9/9$220
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:15 amPDX - MCO
1 stop19h 38mFrontier
Mon 9/228:59 pmMCO - PDX
1 stop28h 35mFrontier
Deal found 9/9$221
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2211:31 amPDX - MCO
1 stop27h 22mMultiple Airlines
Fri 10/33:46 pmMCO - PDX
1 stop11h 26mMultiple Airlines
Deal found 9/10$222
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:52 pmPDX - MCO
1 stop13h 52mFrontier
Mon 11/178:59 pmMCO - PDX
1 stop17h 57mFrontier
Deal found 9/10$223
This Frontier deal was found by Cheapflights users on 9/10. 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.
Sat 11/812:52 pmPDX - MCO
1 stop13h 52mFrontier
Sun 11/166:00 amMCO - PDX
1 stop8h 56mFrontier
Deal found 9/10$224

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 September 11, 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

Thu 10/30

12:40 am-11:09 am

1 stop7h 29m

Orlando

Wed 11/5

4:55 pm-10:42 pm

1 stop8h 47m

$227

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 10/21

1:25 pm-11:59 pm

1 stop7h 34m

Orlando

Fri 10/31

7:20 am-12:50 pm

1 stop8h 30m

$227

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 10/20

7:59 pm-7:21 am

1 stop8h 22m

Orlando

Mon 10/27

6:28 pm-11:57 pm

1 stop8h 29m

$227

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 10/24

12:25 pm-11:58 pm

1 stop8h 33m

Orlando

Thu 10/30

7:20 am-12:50 pm

1 stop8h 30m

$227

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 11/4

6:15 am-6:50 pm

2 stops9h 35m

Orlando

Sat 11/8

6:25 am-1:55 pm

1 stop10h 30m

$242

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 11/26

8:00 pm-7:00 am

1 stop8h 00m

Orlando

Fri 12/5

6:05 am-1:30 pm

1 stop10h 25m

$247

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 12/5

2:35 pm-5:25 am

1 stop11h 50m

Orlando

Sun 12/7

6:40 am-3:05 pm

1 stop11h 25m

$252

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sat 12/6

10:20 am-9:25 pm

1 stop8h 05m

Orlando

Sat 12/13

7:25 am-3:45 pm

1 stop11h 20m

$264

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 9/22

5:01 pm-5:12 am

1 stop9h 11m

Orlando

Sat 9/27

6:40 pm-11:52 pm

1 stop8h 12m

$267

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 10/29

5:10 am-9:20 pm

2 stops13h 10m

Orlando

Sun 11/2

6:35 pm-12:20 am

1 stop8h 45m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 22 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 August 29, 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 September 11, 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 September 7, 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 September 11, 2025.

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

How much does it cost to fly round-trip from Portland to Kissimmee?

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 September 11, 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

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,248 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,937 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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.

  • How long is the flight from Portland to Kissimmee?

    For as low as $227, Delta can have you in Kissimmee from Portland in 7h 29m. 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 $108 on Delta. Other airlines that offer cheap prices include United Airlines from $115 and Southwest from $119 one-way.

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

    Consider Alaska Airlines (49%), Hawaiian Airlines (49%) or LATAM Airlines (44%) 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 $403, our data shows the cheapest flight currently is $168. When looking at the most popular route, (Portland - Orlando), you can expect to pay $144 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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Alternative routes for Portland to Kissimmee

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$244FlexibilityNo cancel feeOn-time65%
FrontierCheapest$126Average$226FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$201Average$493FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$430FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$216Average$451FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$228Average$453FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$236Average$420FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$276Average$483FlexibilityNo cancel feeOn-time85%

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