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Kissimmee

$160+ Cheap flights from Medford (MFR) 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
MFR — MCO
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap flight deals from Medford to Kissimmee

Cheapest flights from Medford to Kissimmee
Explore the most affordable flight options available from Medford to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.

This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 2/235:44 pm
MFR
-
MCO
1 stop10h 56m
Alaska Airlines
Thu 3/59:00 am
MCO
-
MFR
1 stop11h 07m
Alaska Airlines
Deal found 2/2$349
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 3/116:22 pm
MFR
-
MCO
1 stop8h 08m
United Airlines
Tue 3/172:35 pm
MCO
-
MFR
2 stops11h 23m
United Airlines
Deal found 2/2$354
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 2/265:11 pm
MFR
-
MCO
1 stop10h 19m
Multiple Airlines
Wed 3/47:05 pm
MCO
-
MFR
2 stops22h 31m
Multiple Airlines
Deal found 2/2$356
This Delta deal was found by Cheapflights users on 2/2. 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 2/2311:30 am
MFR
-
MCO
2 stops9h 20m
Delta
Tue 3/33:15 pm
MCO
-
MFR
2 stops11h 41m
Delta
Deal found 2/2$359
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 2/265:11 pm
MFR
-
MCO
2 stops43h 53m
Multiple Airlines
Thu 3/57:40 am
MCO
-
MFR
1 stop9h 56m
Multiple Airlines
Deal found 2/2$368
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 2/235:44 pm
MFR
-
MCO
1 stop10h 56m
Alaska Airlines
Wed 3/47:44 am
MCO
-
MFR
2 stops19h 15m
Alaska Airlines
Deal found 2/2$371
This Orbitz deal was found by Cheapflights users on 2/2. 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.
Wed 4/157:40 am
MFR
-
MCO
1 stop19h 12m
Alaska Airlines
Tue 4/217:59 pm
MCO
-
MFR
2 stops21h 58m
Alaska Airlines
Deal found 2/2$372
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 3/111:10 pm
MFR
-
MCO
1 stop13h 30m
Alaska Airlines
Thu 3/195:13 pm
MCO
-
MFR
1 stop8h 23m
Alaska Airlines
Deal found 2/2$376
This Delta deal was found by Cheapflights users on 2/2. 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 5/96:14 am
MFR
-
MCO
1 stop7h 58m
Delta
Thu 5/149:25 am
MCO
-
MFR
1 stop10h 08m
Delta
Deal found 2/2$384
This Alaska Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 5/67:35 am
MFR
-
MCO
1 stop19h 20m
Alaska Airlines
Wed 5/135:34 pm
MCO
-
MFR
1 stop8h 19m
Alaska Airlines
Deal found 2/2$386
This Delta deal was found by Cheapflights users on 2/2. 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 2/231:00 pm
MFR
-
MCO
1 stop7h 50m
Delta
Wed 3/45:30 am
MCO
-
MFR
2 stops9h 41m
Delta
Deal found 2/2$389
This Delta deal was found by Cheapflights users on 2/3. 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 4/275:28 pm
MFR
-
MCO
2 stops14h 15m
Delta
Sat 5/22:15 pm
MCO
-
MFR
2 stops11h 24m
Delta
Deal found 2/3$394

Find flight deals from Medford to Kissimmee

Keep the following information in mind while searching for Medford to Kissimmee flight deals. Data was last updated February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(Alaska Airlines)

One-way from

$160
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$595
Provider with most accurate pricing for Medford-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Medford-Orlando (ORL) flights.
Search Deals
From Medford to Kissimmee
Search Deals
One-way flight from Medford to Kissimmee
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Medford 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 February 5, 2026.
Use the filters below to find and compare flights from Medford to Kissimmee that are best for you.

Fly from

Medford

Fly to

Kissimmee

Route

Depart

Return

Price

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Fri 5/8

6:14 am-5:12 pm

1 stop7h 58m

Orlando

Fri 5/15

6:25 pm-11:50 pm

1 stop8h 25m

$349

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Fri 2/27

1:10 pm-5:40 am

1 stop13h 30m

Orlando

Mon 3/9

8:09 pm-1:02 pm

1 stop19h 53m

$349

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Wed 5/13

12:52 pm-11:44 pm

1 stop7h 52m

Orlando

Mon 5/18

6:10 am-11:47 am

1 stop8h 37m

$349

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Wed 3/11

1:10 pm-5:40 am

1 stop13h 30m

Orlando

Tue 3/17

8:09 pm-12:45 pm

1 stop19h 36m

$349

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Tue 5/5

6:00 am-5:22 pm

1 stop8h 22m

Orlando

Wed 5/13

6:25 pm-11:50 pm

1 stop8h 25m

$349

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Sat 3/7

5:45 am-7:09 pm

1 stop10h 24m

Orlando

Tue 3/10

7:00 am-1:02 pm

1 stop9h 02m

$349

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Mon 4/27

2:12 pm-6:54 am

2 stops13h 42m

Orlando

Fri 5/1

6:10 am-11:47 am

1 stop8h 37m

$354

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Mon 5/11

5:25 pm-10:45 am

2 stops14h 20m

Orlando

Mon 5/18

6:25 pm-11:50 pm

1 stop8h 25m

$354

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Thu 5/14

6:36 pm-10:45 am

2 stops13h 09m

Orlando

Mon 5/18

6:10 am-11:47 am

1 stop8h 37m

$354

MedfordOrlando

MFR - MCO

MFRMCO

Medford

Sat 5/9

5:25 pm-8:47 am

2 stops12h 22m

Orlando

Fri 5/15

6:25 pm-11:50 pm

1 stop8h 25m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 18 results
1
2

Best time to book a flight from Medford to Kissimmee

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

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

Currently, September is the cheapest month in which you can book a flight from Medford to Kissimmee (average of $192). Flying from Medford to Kissimmee in December is currently the most expensive (average of $467). 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.

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 February 5, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and United Airlines from Medford to Kissimmee by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,840 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

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
11,840 reviews
Alaska Airlines
8.0
Very good
11,840 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

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
8,151 reviews
Alaska Airlines
8.0
Very good
11,840 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

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
9,240 reviews
Alaska Airlines
8.0
Very good
11,840 reviews

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.0

Overall

8.0

Comfort

7.8

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 Medford 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 Medford to Kissimmee?

    If you book a flight to Kissimmee from Medford, you will be flying from Medford, which is the city’s only airport. Medford (MFR) is located 3.0 mi from the center of Medford. There are 0 flights from Medford to Kissimmee per day from 4 different airlines.

  • How long is the flight from Medford to Kissimmee?

    There are many flights that can get you from Medford to Kissimmee in 7h 52m. Fly via Delta, Alaska Airlines, or United Airlines to get the fastest option. Medford and Kissimmee are separated by a distance of 2499 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Medford to Kissimmee (average of $192). Flying from Medford to Kissimmee in December is currently the most expensive (average of $467). 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 Medford to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Medford to Kissimmee

Discover the top 4 airlines that operate flights from Medford 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$199Average$443FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$293Average$506FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$311Average$541FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$332Average$405FlexibilityNo cancel feeOn-time71%

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