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$33+ Cheap flights from Kissimmee, FL to Maryland

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 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BWI
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
1 adult, Economy
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Cheap flight deals from Kissimmee to Maryland

Keep the following information in mind while searching for Kissimmee to Maryland flight deals. Data was last updated January 7, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$59
(Frontier)

One-way from

$33
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$133
Provider with most accurate pricing for Orlando (ORL)-Washington, D.C. (WAS) flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Washington, D.C. (WAS) flights.
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From Kissimmee to Maryland
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One-way flight from Kissimmee to Maryland
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Highest demand for flights based on searches. 2% potential increase in price ($3 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Kissimmee to Maryland

Cheapest flights from Kissimmee to Maryland
Explore the most affordable flight options available from Kissimmee to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 7, 2026.

This Frontier deal was found by Cheapflights users on 1/6. 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 1/2210:04 amMCO - BWI
Nonstop2h 23mFrontier
Sun 1/256:15 amBWI - MCO
Nonstop2h 39mFrontier
Deal found 1/6$59
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/238:20 pmMCO - BWI
Nonstop2h 21mFrontier
Mon 1/266:15 amBWI - MCO
Nonstop2h 39mFrontier
Deal found 1/7$60
This Priceline deal was found by Cheapflights users on 1/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/238:20 pmMCO - BWI
Nonstop2h 21mMultiple Airlines
Tue 1/2711:30 amBWI - MCO
Nonstop2h 29mMultiple Airlines
Deal found 1/6$61
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/169:45 pmMCO - BWI
Nonstop2h 21mFrontier
Tue 1/208:00 amBWI - MCO
Nonstop2h 36mFrontier
Deal found 1/6$62
This Super.com deal was found by Cheapflights users on 1/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/227:15 amMCO - PHL
Nonstop2h 44mFrontier
Sat 1/313:54 pmPHL - MCO
Nonstop2h 50mFrontier
Deal found 1/7$62
This Priceline deal was found by Cheapflights users on 1/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/68:20 pmMCO - BWI
Nonstop2h 21mFrontier
Mon 2/96:15 amBWI - MCO
Nonstop2h 39mFrontier
Deal found 1/6$63
This Mytrip deal was found by Cheapflights users on 1/6. 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.
Fri 2/275:01 amMCO - PHL
Nonstop2h 31mFrontier
Mon 3/24:16 pmPHL - MCO
Nonstop2h 50mFrontier
Deal found 1/6$63
This CheapOair deal was found by Cheapflights users on 1/6. 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.
Wed 1/282:45 pmMCO - BWI
Nonstop2h 25mFrontier
Mon 2/96:15 amBWI - MCO
Nonstop2h 39mFrontier
Deal found 1/6$64
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/235:15 pmMCO - PHL
Nonstop2h 33mMultiple Airlines
Fri 1/309:02 pmPHL - MCO
Nonstop2h 49mMultiple Airlines
Deal found 1/5$64
This Frontier deal was found by Cheapflights users on 1/6. 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.
Fri 1/308:20 pmMCO - BWI
Nonstop2h 21mFrontier
Tue 2/38:00 amBWI - MCO
Nonstop2h 36mFrontier
Deal found 1/6$65
This Priceline deal was found by Cheapflights users on 1/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/237:30 pmMCO - PHL
Nonstop2h 33mSpirit Airlines
Fri 1/308:43 pmPHL - MCO
Nonstop2h 45mSpirit Airlines
Deal found 1/5$65
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Sat 1/179:56 pmMCO - BWI
Nonstop2h 21mFrontier
Sat 1/246:15 pmBWI - MCO
Nonstop2h 37mFrontier
Deal found 1/6$66

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Maryland 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 7, 2026.
Use the filters below to find and compare flights from Kissimmee to Maryland that are best for you.

Fly from

Kissimmee

Fly to

Maryland

Route

Depart

Return

Price

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Fri 2/27

5:01 am-7:32 am

Nonstop2h 31m

Philadelphia

Mon 3/2

6:18 pm-9:05 pm

Nonstop2h 47m

$62

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Sat 1/24

8:00 am-10:37 am

Nonstop2h 37m

Philadelphia

Mon 1/26

8:35 pm-11:22 pm

Nonstop2h 47m

$62

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Sat 2/14

6:30 am-9:06 am

Nonstop2h 36m

Philadelphia

Fri 2/20

10:59 pm-1:49 am

Nonstop2h 50m

$68

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Fri 1/30

7:54 pm-10:32 pm

Nonstop2h 38m

Philadelphia

Mon 2/2

5:30 am-8:08 am

Nonstop2h 38m

$70

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Wed 2/18

9:01 am-11:17 am

Nonstop2h 16m

Baltimore/Washington

Fri 2/20

7:09 pm-9:47 pm

Nonstop2h 38m

$71

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Fri 1/30

5:15 pm-7:57 pm

Nonstop2h 42m

Philadelphia

Sat 1/31

6:11 pm-11:59 pm

1 stop5h 48m

$73

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Fri 2/6

7:30 pm-10:03 pm

Nonstop2h 33m

Philadelphia

Sat 2/7

6:18 pm-11:59 pm

1 stop5h 41m

$78

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Fri 2/27

2:39 pm-5:04 pm

Nonstop2h 25m

Baltimore/Washington

Wed 3/4

6:20 am-1:49 pm

1 stop7h 29m

$96

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Thu 2/19

8:48 pm-10:27 am

1 stop13h 39m

Baltimore/Washington

Sat 2/21

4:45 pm-7:14 pm

Nonstop2h 29m

$97

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Fri 2/27

6:54 pm-11:31 pm

1 stop4h 37m

Baltimore/Washington

Mon 3/2

11:30 am-1:59 pm

Nonstop2h 29m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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

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

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

Currently, January is the cheapest month in which you can book a flight from Kissimmee to Maryland (average of $56). Flying from Kissimmee to Maryland in August is currently the most expensive (average of $85). 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 K1S to MD?

Find hourly flight availability from Kissimmee to Maryland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 7, 2026.

It’s typically best to fly out from Kissimmee to Maryland at noon. Doing so could potentially save you 25% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Kissimmee to Maryland. Price data was last updated on January 3, 2026.

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

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. 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 Maryland. Reviews last updated January 7, 2026.
See what other customers who have flown with Southwest, Delta, and American Airlines from Kissimmee to Maryland have to say. 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.
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,025 reviews
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,095 reviews
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,287 reviews
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.7
Fair
3,062 reviews
Southwest
8.0
Very good
4,248 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Maryland. 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 Kissimmee to Maryland?

    Departing from Kissimmee to Maryland will take you 2h 31m. Airlines will cover a distance of 862 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Kissimmee to Maryland one-way?

    One-way options have recently been found by users for as low as $36 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $39 and Southwest from $78 one-way.

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

    While some choose either Orlando - Washington, D.C. Reagan-National or Orlando - Philadelphia, Orlando - Washington, D.C. Dulles Intl is the most popular route from Kissimmee to Maryland.

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

    No one likes to see their flight delayed. When booking a flight from Kissimmee to Maryland consider choosing Frontier (83%), Spirit Airlines (75%) or Southwest (69%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Kissimmee to Maryland?

    On average you can expect to pay $130 for a flight from Kissimmee to Maryland. The cheapest flight overall is $32 while the most popular route, (Orlando - Washington, D.C. Dulles Intl) is currently priced at $58.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Kissimmee to Maryland (average of $56). Flying from Kissimmee to Maryland in August is currently the most expensive (average of $85). 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.

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Alternative routes for Kissimmee to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Kissimmee to Maryland

Discover the top 6 airlines that operate flights from Kissimmee to Maryland. 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 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$57Average$146FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$76Average$141FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$118Average$164FlexibilityNo cancel feeOn-time88%
DeltaCheapest$147Average$450FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$181Average$304FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$200Average$500FlexibilityNo cancel feeOn-time71%

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