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Kissimmee

$83+ Cheap flights from Oregon 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Oregon to Kissimmee

Cheapest flights from Oregon to Kissimmee
Explore the most affordable flight options available from Oregon to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. 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 12/61:57 pmBOI - MCO
1 stop7h 56mAmerican Airlines
Wed 12/105:13 amMCO - BOI
1 stop9h 20mAmerican Airlines
Deal found 10/30$187
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:30 amPDX - MCO
2 stops9h 10mSouthwest
Fri 12/124:10 pmMCO - PDX
1 stop11h 05mSouthwest
Deal found 10/28$190
This Southwest deal was found by Cheapflights users on 10/29. 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.
Wed 12/32:40 pmBOI - MCO
1 stop12h 45mSouthwest
Sat 12/66:25 amMCO - BOI
1 stop10h 45mSouthwest
Deal found 10/29$192
This Booking.com deal was found by Cheapflights users on 10/30. 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 12/89:31 amPDX - MCO
1 stop17h 19mFrontier
Sat 12/137:20 amMCO - PDX
1 stop29h 14mFrontier
Deal found 10/30$195
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/89:31 amPDX - MCO
1 stop17h 19mFrontier
Thu 12/117:20 amMCO - PDX
1 stop29h 14mFrontier
Deal found 10/28$196
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/911:54 amPDX - MCO
1 stop6h 53mDelta
Mon 12/155:01 pmMCO - PDX
1 stop10h 03mDelta
Deal found 10/29$197
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/98:45 amBOI - MCO
1 stop6h 38mDelta
Mon 12/155:01 pmMCO - BOI
1 stop9h 41mDelta
Deal found 10/29$197
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/181:26 pmPDX - MCO
1 stop13h 18mFrontier
Mon 11/2412:20 pmMCO - PDX
2 stops29h 47mFrontier
Deal found 10/28$207
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:42 pmPDX - MCO
1 stop8h 26mAmerican Airlines
Tue 11/181:28 pmMCO - PDX
1 stop9h 21mAmerican Airlines
Deal found 10/28$209
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1512:52 pmPDX - MCO
1 stop13h 52mFrontier
Sat 11/228:35 pmMCO - PDX
1 stop21h 32mFrontier
Deal found 10/28$211
This Frontier deal was found by Cheapflights users on 10/30. 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 11/1312:52 pmPDX - MCO
1 stop13h 52mFrontier
Sun 11/166:00 amMCO - PDX
1 stop8h 56mFrontier
Deal found 10/30$213
This Booking.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/1312:52 pmPDX - MCO
1 stop22h 58mFrontier
Mon 11/176:00 amMCO - PDX
1 stop8h 56mFrontier
Deal found 10/29$214

Cheap flight deals from Oregon to Kissimmee

Keep the following information in mind while searching for Oregon to Kissimmee flight deals. Data was last updated October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$129
(Kiwi.com)

One-way from

$83
(Booking.com)

Popular in

March

Cheapest in

July

Average price

$356
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 Oregon to Kissimmee
Search Deals
One-way flight from Oregon to Kissimmee
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 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 Oregon 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 October 30, 2025.
Use the filters below to find and compare flights from Oregon to Kissimmee that are best for you.

Fly from

Oregon

Fly to

Kissimmee

Route

Depart

Return

Price

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Sat 12/6

1:57 pm-11:53 pm

1 stop7h 56m

Orlando

Wed 12/10

5:13 am-12:33 pm

1 stop9h 20m

$187

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 11/19

1:53 pm-11:59 pm

1 stop7h 06m

Orlando

Wed 12/3

4:50 pm-10:56 pm

1 stop9h 06m

$197

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Mon 12/8

12:32 am-1:39 pm

1 stop10h 07m

Orlando

Mon 12/15

5:01 pm-12:04 am

1 stop10h 03m

$197

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 12/3

11:54 am-11:47 pm

1 stop8h 53m

Orlando

Mon 12/8

6:15 pm-12:15 am

1 stop9h 00m

$197

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 12/12

12:32 am-11:32 am

1 stop8h 00m

Orlando

Thu 12/18

6:15 pm-12:15 am

1 stop9h 00m

$197

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 1/23

5:23 am-5:12 pm

1 stop8h 49m

Orlando

Tue 1/27

5:30 am-10:49 am

1 stop8h 19m

$197

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Mon 2/16

7:30 pm-7:43 am

1 stop10h 13m

Orlando

Mon 2/23

9:20 am-6:25 pm

1 stop11h 05m

$197

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Tue 4/14

1:15 pm-12:06 am

1 stop8h 51m

Orlando

Wed 4/15

7:00 pm-12:11 am

1 stop7h 11m

$197

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Mon 4/13

11:30 pm-8:44 am

1 stop7h 14m

Orlando

Wed 4/15

7:00 pm-12:11 am

1 stop7h 11m

$197

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Mon 4/13

7:30 pm-7:46 am

1 stop10h 16m

Orlando

Tue 4/14

7:00 pm-12:11 am

1 stop7h 11m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Oregon to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Oregon 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 Oregon to Kissimmee

What is the cheapest month to book a flight from Oregon to Kissimmee?

Currently, January is the cheapest month in which you can book a flight from Oregon to Kissimmee (average of $129). Flying from Oregon 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 OR to K1S?

Find hourly flight availability from Oregon 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 October 30, 2025.

One of the essential ways to save on airfare from Oregon 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 17% on airfare.

What is the cheapest day to fly from Oregon to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Oregon to Kissimmee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oregon 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.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oregon to Kissimmee?

    Airlines like American Airlines, Delta, and Alaska Airlines fly from Oregon to Kissimmee in about 7h 06m. The time it takes to get you to your destination can typically vary by up to 50m. Oregon 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 Oregon to Kissimmee one-way?

    One-way options have recently been found by users for as low as $94 on American Airlines. Other airlines that offer cheap prices include Delta from $99 and United Airlines from $120 one-way.

  • What are the most popular routes from Oregon to Kissimmee?

    The most popular route from Oregon to Kissimmee is Portland - Orlando. You may also consider Boise Air Term. Gowen Fld - Orlando or Eugene - Orlando.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Oregon to Kissimmee on time: Sun Country Air (100%), Alaska Airlines (85%), Hawaiian Airlines (85%).

  • What are the cheapest flights from Oregon to Kissimmee?

    Looking for the cheapest flight from Oregon to Kissimmee? While on average our users pay $1,162, our data indicates the cheapest price to be $178. The most popular route (Portland - Orlando), is priced around $169.

  • Can I find deals for flights from Oregon to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Oregon to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Kissimmee.

  • Can I find deals for business class flights from Oregon to Kissimmee?

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to Kissimmee?

    Currently, January is the cheapest month in which you can book a flight from Oregon to Kissimmee (average of $129). Flying from Oregon 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

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Top 9 airlines flying from Oregon to Kissimmee

Discover the top 9 airlines that operate flights from Oregon 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$85Average$181FlexibilityNo cancel feeOn-time65%
FrontierCheapest$128Average$240FlexibilityNo cancel feeOn-time62%
DeltaCheapest$198Average$415FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$201Average$476FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$206Average$495FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$207Average$513FlexibilityNo cancel feeOn-time75%
Sun Country AirCheapest$228Average$440FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$236Average$510FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$276Average$484FlexibilityNo cancel feeOn-time85%

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