HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 32 days in advance, depart on a Monday or Tuesday 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 April 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$211
(CheapOair)

One-way from

$104
(Delta)

Popular in

March

Cheapest in

January

Average price

$388
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. 4% potential increase in price ($17 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 April 2025
Search Deals

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 April 29, 2025.

This CheapOair deal was found by Cheapflights users on 4/29. 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.
Sat 5/36:20 amPDX - MCO
1 stop20h 43mFrontier
Fri 5/98:59 pmMCO - PDX
1 stop30h 39mFrontier
Deal found 4/29$211
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/175:35 amPDX - MCO
2 stops10h 10mSouthwest
Fri 8/227:10 amMCO - PDX
1 stop11h 40mSouthwest
Deal found 4/29$212
This FlightHub deal was found by Cheapflights users on 4/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/271:37 pmPDX - MCO
2 stops22h 51mSpirit Airlines
Tue 6/310:25 amMCO - PDX
1 stop9h 20mSpirit Airlines
Deal found 4/29$217
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:20 amPDX - MCO
1 stop15h 13mMultiple Airlines
Tue 6/310:25 amMCO - PDX
1 stop9h 20mMultiple Airlines
Deal found 4/29$247
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/35:26 amPDX - MCO
1 stop10h 09mAmerican Airlines
Sun 6/156:00 amMCO - PDX
1 stop11h 24mAmerican Airlines
Deal found 4/29$262
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/15:05 pmPDX - MCO
1 stop9h 37mDelta
Thu 6/126:30 pmMCO - PDX
1 stop8h 59mDelta
Deal found 4/29$275
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/35:30 pmPDX - MCO
1 stop9h 15mAlaska Airlines
Tue 6/105:50 pmMCO - PDX
Nonstop6h 00mAlaska Airlines
Deal found 4/28$308
This Sun Country Air deal was found by Cheapflights users on 4/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/165:58 pmPDX - MCO
1 stop17h 12mSun Country Air
Sun 6/228:11 pmMCO - PDX
1 stop29h 35mSun Country Air
Deal found 4/28$355
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 6/31:25 pmPDX - MCO
2 stops13h 11mUnited Airlines
Tue 6/107:12 amMCO - PDX
1 stop7h 44mUnited Airlines
Deal found 4/29$362
This Hawaiian Airlines deal was found by Cheapflights users on 4/29. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/35:30 pmPDX - MCO
1 stop9h 15mHawaiian Airlines
Sun 6/155:50 pmMCO - PDX
Nonstop6h 00mHawaiian Airlines
Deal found 4/29$398

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 April 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

Sat 5/3

6:20 am-6:03 am

1 stop20h 43m

Orlando

Fri 5/9

8:59 pm-12:38 am

1 stop30h 39m

$211

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 5/27

1:37 pm-3:28 pm

2 stops22h 51m

Orlando

Tue 6/3

10:25 am-4:45 pm

1 stop9h 20m

$217

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sat 5/24

1:55 pm-12:33 am

1 stop7h 38m

Orlando

Fri 5/30

6:52 am-2:34 pm

1 stop10h 42m

$233

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 5/19

6:20 am-12:33 am

1 stop15h 13m

Orlando

Tue 6/3

10:25 am-4:45 pm

1 stop9h 20m

$247

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sun 6/1

5:05 pm-5:42 am

1 stop9h 37m

Orlando

Thu 6/12

6:30 pm-12:29 am

1 stop8h 59m

$275

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 6/3

5:30 pm-5:45 am

1 stop9h 15m

Orlando

Tue 6/10

5:50 pm-8:50 pm

Nonstop6h 00m

$308

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 6/4

10:00 am-6:37 pm

Nonstop5h 37m

Orlando

Tue 6/10

5:50 pm-8:50 pm

Nonstop6h 00m

$318

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 6/16

11:59 pm-2:10 pm

1 stop11h 11m

Orlando

Sun 6/22

8:11 pm-10:46 pm

1 stop29h 35m

$355

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 6/3

11:00 am-9:46 pm

1 stop7h 46m

Orlando

Wed 6/11

8:18 am-6:35 pm

2 stops13h 17m

$362

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Thu 6/5

1:15 pm-12:25 am

1 stop8h 10m

Orlando

Wed 6/11

6:50 am-2:30 pm

2 stops10h 40m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 21 results
1
2
3

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 April 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 $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 April 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 March 30, 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 April 29, 2025.

The most flights from PDX to K1S are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 April 29, 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
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

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
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

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
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

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
2,405 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

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 are 2 flights 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 Frontier from $107 and Spirit Airlines from $124 one-way.

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

    Consider LATAM Airlines (92%), Alaska Airlines (84%) or Hawaiian Airlines (84%) 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 $833, our data shows the cheapest flight currently is $184. 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Orlando flights
Portland to Miami flights
Portland to Fort Lauderdale flights
Portland to Tampa flights
Boise to Orlando flights
Portland to Fort Myers flights
Boise to Tampa flights
Portland to Sarasota flights
Boise to Miami flights
Portland to Jacksonville flights
Portland to Pensacola flights
Boise to Jacksonville flights
Boise to Pensacola flights
Boise to Valparaiso flights
Portland to Key West flights
Eugene to Orlando flights
Portland to Panama City flights
Boise to Fort Lauderdale flights
Medford to Orlando flights
Eugene to Miami flights
Portland to Valparaiso flights
Portland to Daytona Beach flights
Portland to West Palm Beach flights
Redmond to Tampa flights
Eugene to Jacksonville flights
Portland to Melbourne flights
Medford to Tampa flights
Medford to Miami flights
Redmond to Orlando flights
Redmond to Miami flights
Medford to Fort Lauderdale flights
Boise to Key West flights
Boise to Panama City flights
Eugene to Sarasota flights
Eugene to Valparaiso flights
Redmond to West Palm Beach flights
Redmond to Fort Lauderdale flights
Eugene to Fort Lauderdale flights
Yakima to Orlando flights
Eugene to Fort Myers flights
Eugene to Pensacola flights
Portland to Gainesville flights
Redmond to Sarasota flights
Redmond to Fort Myers flights
Eugene to Tampa flights
Redmond to Jacksonville flights
Medford to Panama City flights
Portland to Tallahassee flights
Eugene to Gainesville flights
Boise to West Palm Beach flights

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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$210FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$223FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$142Average$394FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$206Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$206Average$412FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$479FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$235Average$443FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$242Average$418FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$304Average$538FlexibilityNo cancel feeOn-time85%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.