HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$120+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
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 81 days in advance, depart on a Wednesday or Thursday and return on a Thursday

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 octubre 28, 2025.

This Southwest deal was found by Cheapflights users on 10/26. 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.
sáb. 12/134:35 pmPDX - MCO
1 stop11h 30mSouthwest
jue. 12/187:35 pmMCO - PDX
1 stop7h 40mSouthwest
Deal found 10/26$184
This Southwest deal was found by Cheapflights users on 10/27. 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.
sáb. 12/62:30 pmPDX - MCO
1 stop12h 20mSouthwest
vie. 12/124:10 pmMCO - PDX
1 stop11h 05mSouthwest
Deal found 10/27$190
This CheapOair deal was found by Cheapflights users on 10/26. 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.
lun. 12/89:31 amPDX - MCO
1 stop17h 19mFrontier
jue. 12/117:20 amMCO - PDX
1 stop29h 14mFrontier
Deal found 10/26$196
This Delta deal was found by Cheapflights users on 10/28. 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.
sáb. 12/610:10 pmPDX - MCO
1 stop7h 51mDelta
sáb. 12/139:00 amMCO - PDX
1 stop9h 33mDelta
Deal found 10/28$197
This Mytrip deal was found by Cheapflights users on 10/27. 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.
lun. 12/89:31 amPDX - MCO
1 stop17h 19mFrontier
sáb. 12/137:20 amMCO - PDX
1 stop29h 14mFrontier
Deal found 10/27$206
This American Airlines deal was found by Cheapflights users on 10/27. 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.
jue. 12/111:45 pmPDX - MCO
1 stop7h 38mAmerican Airlines
jue. 12/185:00 amMCO - PDX
1 stop9h 00mAmerican Airlines
Deal found 10/27$208
This American Airlines deal was found by Cheapflights users on 10/26. 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.
jue. 11/135:42 pmPDX - MCO
1 stop8h 26mAmerican Airlines
mar. 11/185:15 pmMCO - PDX
1 stop9h 11mAmerican Airlines
Deal found 10/26$209
This CheapOair deal was found by Cheapflights users on 10/27. 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.
sáb. 11/1512:52 pmPDX - MCO
1 stop13h 52mFrontier
sáb. 11/228:35 pmMCO - PDX
1 stop21h 32mFrontier
Deal found 10/27$211
This Southwest deal was found by Cheapflights users on 10/26. 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.
lun. 11/175:55 amPDX - MCO
2 stops9h 30mSouthwest
lun. 11/246:45 pmMCO - PDX
1 stop8h 35mSouthwest
Deal found 10/26$214
This Delta deal was found by Cheapflights users on 10/27. 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.
mié. 12/1012:32 amPDX - MCO
1 stop8h 00mDelta
lun. 12/155:01 pmMCO - PDX
1 stop10h 03mDelta
Deal found 10/27$218
This Frontier deal was found by Cheapflights users on 10/27. 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.
sáb. 11/812:52 pmPDX - MCO
1 stop13h 52mFrontier
jue. 11/136:00 amMCO - PDX
1 stop8h 56mFrontier
Deal found 10/27$222
This American Airlines deal was found by Cheapflights users on 10/27. 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.
lun. 12/810:45 pmPDX - MCO
1 stop8h 27mAmerican Airlines
sáb. 12/136:42 amMCO - PDX
1 stop8h 56mAmerican Airlines
Deal found 10/27$224

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 octubre 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$184
(Southwest)

One-way from

$120
(Southwest)

Popular in

June

Cheapest in

January

Average price

$394
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. 7% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 octubre 28, 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

sáb. 12/13

4:35 pm-7:05 am

1 stop11h 30m

Orlando

jue. 12/18

7:35 pm-12:15 am

1 stop7h 40m

$184

PortlandOrlando

PDX - MCO

PDXMCO

Portland

sáb. 12/6

5:25 pm-6:00 am

1 stop9h 35m

Orlando

sáb. 12/13

6:40 am-12:54 pm

1 stop9h 14m

$197

PortlandOrlando

PDX - MCO

PDXMCO

Portland

dom. 12/14

12:32 am-1:39 pm

1 stop10h 07m

Orlando

jue. 1/15

6:22 pm-12:17 am

1 stop8h 55m

$218

PortlandOrlando

PDX - MCO

PDXMCO

Portland

vie. 1/23

11:59 am-12:59 am

1 stop10h 00m

Orlando

mar. 1/27

11:10 am-8:27 pm

1 stop12h 17m

$218

PortlandOrlando

PDX - MCO

PDXMCO

Portland

mié. 11/12

12:35 am-11:24 am

1 stop7h 49m

Orlando

mar. 11/18

6:35 pm-11:58 pm

1 stop8h 23m

$238

PortlandOrlando

PDX - MCO

PDXMCO

Portland

mié. 11/12

7:59 pm-7:55 am

1 stop8h 56m

Orlando

dom. 11/16

5:30 am-10:43 am

1 stop8h 13m

$239

PortlandOrlando

PDX - MCO

PDXMCO

Portland

jue. 1/8

2:15 pm-5:25 am

1 stop12h 10m

Orlando

dom. 1/11

6:30 am-1:45 pm

1 stop10h 15m

$243

PortlandOrlando

PDX - MCO

PDXMCO

Portland

dom. 11/9

12:35 am-11:24 am

1 stop7h 49m

Orlando

sáb. 11/15

6:55 am-12:48 pm

1 stop8h 53m

$299

PortlandOrlando

PDX - MCO

PDXMCO

Portland

sáb. 12/13

4:35 pm-7:05 am

1 stop11h 30m

Orlando

dom. 12/21

6:00 pm-12:25 am

2 stops9h 25m

$309

PortlandOrlando

PDX - MCO

PDXMCO

Portland

lun. 12/8

5:30 am-6:45 pm

2 stops10h 15m

Orlando

sáb. 12/13

1:45 pm-8:35 pm

2 stops9h 50m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 22 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 October 24, 2025.

Booking 81 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, January is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $129). Flying from Portland to Kissimmee in December is currently the most expensive (average of $208). 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 octubre 28, 2025.

One of the essential ways to save on airfare from Portland to Kissimmee is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 42% on airfare.

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 October 19, 2025.

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

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 octubre 28, 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
11,203 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,203 reviews
Alaska Airlines
8.0
Very good
11,203 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,240 reviews
Alaska Airlines
8.0
Very good
11,203 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,994 reviews
Alaska Airlines
8.0
Very good
11,203 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
9,001 reviews
Alaska Airlines
8.0
Very good
11,203 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,032 reviews
Alaska Airlines
8.0
Very good
11,203 reviews

Crew

8.5

Boarding

8.1

Food

7.1

Comfort

7.8

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 0 flights from Portland to Kissimmee per day from 9 different airlines.

  • How long is the flight from Portland to Kissimmee?

    For as low as $197, Southwest can have you in Kissimmee from Portland in 9h 35m. 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 $120 on Frontier. Other airlines that offer cheap prices include United Airlines from $120 and Delta from $120 one-way.

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

    Consider Sun Country Air (100%), Alaska Airlines (85%) or Hawaiian Airlines (85%) 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 $1,162, our data shows the cheapest flight currently is $178. When looking at the most popular route, (Portland - Orlando), you can expect to pay $179 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, January is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $129). Flying from Portland to Kissimmee in December is currently the most expensive (average of $208). 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 Tampa flights
Portland to Fort Lauderdale flights
Boise to Orlando flights
Boise to Miami flights
Eugene to Orlando flights
Portland to Jacksonville flights
Boise to Fort Lauderdale flights
Portland to Pensacola flights
Portland to Fort Myers flights
Boise to Tampa flights
Portland to Sarasota flights
Portland to West Palm Beach flights
Eugene to Tampa flights
Portland to Tallahassee flights
Boise to Pensacola flights
Eugene to Fort Lauderdale flights
Medford to Orlando flights
Redmond to Fort Lauderdale flights
Redmond to Orlando flights
Medford to Miami flights
Eugene to Miami flights
Redmond to Miami flights
Redmond to Tampa flights
Portland to Gainesville flights
Portland to Daytona Beach flights
Medford to Fort Lauderdale flights
Boise to Valparaiso flights
Eugene to Fort Myers flights
Portland to Melbourne flights
Portland to Key West flights
Eugene to Jacksonville flights
Yakima to Orlando flights
Portland to Panama City flights
Boise to Fort Myers flights
Boise to Jacksonville flights
Eugene to Melbourne flights
Medford to Pensacola flights
Boise to Daytona Beach flights
Portland to Valparaiso flights
Redmond to West Palm Beach flights
Redmond to Jacksonville flights
Boise to Panama City flights
Eugene to West Palm Beach flights
Boise to Key West flights
Medford to Tampa flights
Boise to Tallahassee flights
Portland to Valdosta flights
Redmond to Fort Myers 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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$181FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$240FlexibilityNo cancel feeOn-time62%
DeltaCheapest$198Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$201Average$404FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$413FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$207Average$467FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$228Average$440FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$236Average$400FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$276Average$484FlexibilityNo 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.