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Kissimmee

$99+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$202
(American Airlines)

One-way from

$99
(Delta)

Popular in

March

Cheapest in

January

Average price

$396
Provider with most accurate pricing for Portland-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Portland-Orlando (ORL) flights.
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From Oregon to Kissimmee
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One-way flight from Oregon to Kissimmee
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Highest demand for flights based on searches. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 1, 2025.

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.
Wed 9/31:41 pmBOI - MCO
1 stop8h 40mAmerican Airlines
Tue 9/94:17 pmMCO - BOI
2 stops9h 19mAmerican Airlines
Deal found 4/29$202
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.
Fri 9/126:10 amPDX - MCO
2 stops10h 50mSouthwest
Fri 9/199:20 amMCO - PDX
1 stop9h 30mSouthwest
Deal found 4/29$212
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.
Wed 6/115:06 pmPDX - MCO
1 stop9h 33mDelta
Wed 7/234:20 pmMCO - PDX
1 stop9h 18mDelta
Deal found 4/29$232
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/198:59 pmBOI - MCO
1 stop8h 40mMultiple Airlines
Thu 5/226:00 amMCO - BOI
1 stop7h 51mMultiple Airlines
Deal found 4/29$233
This Delta deal was found by Cheapflights users on 5/1. 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 5/3011:59 pmBOI - MCO
1 stop6h 37mDelta
Wed 6/46:24 pmMCO - BOI
1 stop7h 58mDelta
Deal found 5/1$238
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 5/275:40 pmPDX - MCO
2 stops18h 48mSpirit Airlines
Sat 5/315:15 amMCO - PDX
2 stops14h 30mSpirit Airlines
Deal found 4/29$239
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/176:05 amBOI - MCO
2 stops10h 40mSouthwest
Sat 8/234:00 pmMCO - BOI
1 stop8h 10mSouthwest
Deal found 4/30$243
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 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 5/276:43 pmPDX - MCO
1 stop7h 53mUnited Airlines
Tue 6/31:52 pmMCO - PDX
1 stop9h 00mUnited Airlines
Deal found 4/29$257
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.
Fri 7/186:00 amPDX - MCO
1 stop10h 44mAmerican Airlines
Tue 7/292:29 pmMCO - PDX
1 stop10h 37mAmerican Airlines
Deal found 4/29$259
This Hawaiian Airlines deal was found by Cheapflights users on 4/30. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/128:46 pmBOI - MCO
1 stop8h 54mHawaiian Airlines
Sun 8/177:20 amMCO - BOI
1 stop9h 44mHawaiian Airlines
Deal found 4/30$264

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 May 1, 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

Wed 9/3

1:41 pm-12:21 am

1 stop8h 40m

Orlando

Tue 9/9

4:17 pm-11:36 pm

2 stops9h 19m

$202

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Sun 5/18

6:35 am-2:58 pm

1 stop29h 23m

Orlando

Sat 5/24

6:00 am-12:17 am

1 stop21h 17m

$211

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Fri 9/12

6:10 am-8:00 pm

2 stops10h 50m

Orlando

Fri 9/19

9:20 am-3:50 pm

1 stop9h 30m

$212

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Wed 6/11

5:06 pm-5:39 am

1 stop9h 33m

Orlando

Wed 7/23

4:20 pm-10:38 pm

1 stop9h 18m

$232

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Mon 5/19

8:59 pm-7:39 am

1 stop8h 40m

Orlando

Thu 5/22

6:00 am-11:51 am

1 stop7h 51m

$233

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Fri 5/30

11:59 pm-8:36 am

1 stop6h 37m

Orlando

Wed 6/4

6:24 pm-12:22 am

1 stop7h 58m

$238

PortlandOrlando

PDX - MCO

PDXMCO

Portland

Tue 5/27

5:40 pm-3:28 pm

2 stops18h 48m

Orlando

Sat 5/31

5:15 am-4:45 pm

2 stops14h 30m

$239

BoiseOrlando

BOI - MCO

BOIMCO

Boise Air Term. Gowen Fld

Sun 8/17

6:05 am-6:45 pm

2 stops10h 40m

Orlando

Sat 8/23

4:00 pm-10:10 pm

1 stop8h 10m

$243

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

Tue 5/27

6:43 pm-5:36 am

1 stop7h 53m

Orlando

Tue 6/3

1:52 pm-7:52 pm

1 stop9h 00m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 58 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, May is the cheapest month in which you can book a flight from Oregon to Kissimmee (average of $206). Flying from Oregon 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 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 May 1, 2025.

When flying from Oregon to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 May 1, 2025.
Read through reviews of airlines operating flights from Oregon to Kissimmee, such as Alaska Airlines, Southwest and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.1

Crew

8.5

Food

7.1

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.1

Crew

8.5

Food

7.1

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.1

Crew

8.5

Food

7.1

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.1

Crew

8.5

Food

7.1

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
2,408 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.1

Crew

8.5

Food

7.1

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
9,972 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.1

Boarding

8.1

Crew

8.5

Food

7.1

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 Oregon to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 $99 on Delta. Other airlines that offer cheap prices include American Airlines from $104 and Frontier from $106 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 Medford - 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: LATAM Airlines (92%), Alaska Airlines (84%), Hawaiian Airlines (84%).

  • What are the cheapest flights from Oregon to Kissimmee?

    Looking for the cheapest flight from Oregon to Kissimmee? While on average our users pay $833, our data indicates the cheapest price to be $184. The most popular route (Portland - Orlando), is priced around $199.

  • 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, May is the cheapest month in which you can book a flight from Oregon to Kissimmee (average of $206). Flying from Oregon 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

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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 May 1, 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$445FlexibilityNo cancel feeOn-time71%
DeltaCheapest$206Average$479FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$505FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$235Average$512FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$242Average$517FlexibilityNo cancel feeOn-time69%
Hawaiian AirlinesCheapest$304Average$538FlexibilityNo cancel feeOn-time85%

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