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Kissimmee

$130+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Kissimmee are usually found in January or September, booked 88 days in advance, depart on a Wednesday or Monday and return on a Friday

Cheap 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 January 27, 2026.

This CheapOair deal was found by Cheapflights users on 1/26. 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.
Thu 4/3011:48 am
PDX
-
MCO
1 stop24h 25m
Frontier
Sat 5/98:19 pm
MCO
-
PDX
1 stop15h 40m
Frontier
Deal found 1/26$212
This Orbitz deal was found by Cheapflights users on 1/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:53 am
PDX
-
MCO
1 stop15h 54m
Frontier
Sun 4/194:02 pm
MCO
-
PDX
1 stop22h 55m
Frontier
Deal found 1/25$215
This Delta deal was found by Cheapflights users on 1/25. 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.
Sat 3/145:40 pm
PDX
-
MCO
1 stop10h 45m
Delta
Tue 3/176:05 am
MCO
-
PDX
1 stop9h 09m
Delta
Deal found 1/25$217
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:30 pm
PDX
-
MCO
1 stop7h 30m
Delta
Tue 7/216:40 pm
MCO
-
PDX
1 stop7h 54m
Delta
Deal found 1/26$218
This Frontier deal was found by Cheapflights users on 1/27. 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.
Wed 4/221:48 pm
PDX
-
MCO
1 stop12h 55m
Frontier
Sat 4/258:19 pm
MCO
-
PDX
1 stop15h 40m
Frontier
Deal found 1/27$222
This Southwest deal was found by Cheapflights users on 1/26. 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.
Mon 2/236:35 am
PDX
-
MCO
2 stops10h 25m
Southwest
Tue 3/107:00 am
MCO
-
PDX
1 stop8h 35m
Southwest
Deal found 1/26$224
This CheapOair deal was found by Cheapflights users on 1/26. 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.
Fri 5/19:53 am
PDX
-
MCO
1 stop15h 54m
Frontier
Wed 5/68:28 pm
MCO
-
PDX
1 stop17h 35m
Frontier
Deal found 1/26$226
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:04 pm
PDX
-
MCO
1 stop24h 05m
Frontier
Tue 3/174:02 pm
MCO
-
PDX
2 stops19h 56m
Frontier
Deal found 1/26$227
This Delta deal was found by Cheapflights users on 1/25. 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 2/95:08 pm
PDX
-
MCO
1 stop10h 07m
Delta
Wed 2/185:30 am
MCO
-
PDX
1 stop8h 22m
Delta
Deal found 1/25$228
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Tue 3/1711:46 am
PDX
-
MCO
1 stop8h 11m
American Airlines
Tue 3/245:46 pm
MCO
-
PDX
1 stop9h 34m
American Airlines
Deal found 1/26$229
This Southwest deal was found by Cheapflights users on 1/25. 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.
Wed 3/42:15 pm
PDX
-
MCO
1 stop12h 10m
Southwest
Mon 3/167:55 am
MCO
-
PDX
1 stop13h 05m
Southwest
Deal found 1/25$230
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Thu 4/169:53 am
PDX
-
MCO
1 stop15h 54m
Frontier
Mon 4/206:00 am
MCO
-
PDX
1 stop8h 03m
Frontier
Deal found 1/27$233

Find flight deals from Portland to Kissimmee

Keep the following information in mind while searching for Portland to Kissimmee flight deals. Data was last updated January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$212
(CheapOair)

One-way from

$130
(United Airlines)

Popular in

June

Cheapest in

January

Average price

$336
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. 8% potential increase in price ($36 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 January 2026
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 January 27, 2026.
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

Mon 2/9

5:08 pm-6:15 am

1 stop10h 07m

Orlando

Wed 2/18

5:30 am-10:52 am

1 stop8h 22m

$228

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 2/20

5:10 pm-6:35 am

1 stop10h 25m

Orlando

Sat 2/28

6:00 am-12:02 pm

1 stop9h 02m

$238

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 3/31

5:02 pm-5:53 am

1 stop9h 51m

Orlando

Fri 4/3

6:29 pm-11:59 pm

1 stop8h 30m

$238

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 5/25

2:30 pm-12:57 am

1 stop7h 27m

Orlando

Thu 5/28

5:30 am-10:44 am

1 stop8h 14m

$238

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 2/24

6:30 am-6:50 pm

1 stop9h 20m

Orlando

Tue 3/3

2:35 pm-10:15 pm

2 stops10h 40m

$243

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 3/24

7:45 pm-7:40 am

1 stop8h 55m

Orlando

Wed 3/25

6:29 pm-11:59 pm

1 stop8h 30m

$258

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Thu 3/5

2:30 pm-6:15 am

1 stop12h 45m

Orlando

Wed 3/11

3:55 pm-11:10 pm

2 stops10h 15m

$260

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 3/10

10:30 pm-9:46 am

1 stop8h 16m

Orlando

Thu 3/12

5:30 am-10:30 am

1 stop8h 00m

$268

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 3/9

10:58 am-11:22 pm

1 stop9h 24m

Orlando

Thu 3/12

4:13 pm-9:53 pm

1 stop8h 40m

$268

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 7/13

2:30 pm-1:00 am

1 stop7h 30m

Orlando

Wed 7/22

6:40 pm-11:34 pm

1 stop7h 54m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 23 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 January 23, 2026.

Booking 88 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, October is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $154). Flying from Portland to Kissimmee in February is currently the most expensive (average of $206). 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 January 27, 2026.

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 50% on airfare.

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 January 27, 2026.

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).

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 January 27, 2026.
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
11,795 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,795 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,268 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,118 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,205 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,197 reviews
Alaska Airlines
8.0
Very good
11,795 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 8 different airlines.

  • How long is the flight from Portland to Kissimmee?

    For as low as $243, Delta can have you in Kissimmee from Portland in 9h 20m. 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 $82 on Frontier. Other airlines that offer cheap prices include Southwest from $98 and American Airlines from $98 one-way.

  • What are the cheapest flights from Portland to Kissimmee?

    While on average a flight from Portland to Kissimmee is generally $351, our data shows the cheapest flight currently is $199. When looking at the most popular route, (Portland - Orlando), you can expect to pay $184 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, October is the cheapest month in which you can book a flight from Portland to Kissimmee (average of $154). Flying from Portland to Kissimmee in February is currently the most expensive (average of $206). 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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Alternative routes for Portland to Kissimmee

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Top 8 airlines flying from Portland to Kissimmee

Discover the top 8 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$244FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$324FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$149Average$481FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$178Average$345FlexibilityNo cancel feeOn-time71%
Spirit AirlinesCheapest$200Average$216FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$206Average$401FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$381FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$241Average$485FlexibilityNo cancel feeOn-time75%

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