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$39+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BWI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Gotogate deal was found by Cheapflights users on 11/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:06 pmMCO - PHL
Nonstop2h 33mFrontier
Sun 12/710:00 pmPHL - MCO
Nonstop2h 35mFrontier
Deal found 11/13$70
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/97:05 amMCO - BWI
Nonstop2h 17mMultiple Airlines
Sun 12/149:43 pmBWI - MCO
Nonstop2h 36mMultiple Airlines
Deal found 11/12$71
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Wed 12/33:05 pmMCO - BWI
Nonstop2h 19mSpirit Airlines
Sat 12/138:00 pmBWI - MCO
Nonstop2h 31mSpirit Airlines
Deal found 11/11$72
This Super.com deal was found by Cheapflights users on 11/12. 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 11/278:00 amMCO - IAD
Nonstop2h 17mFrontier
Mon 12/18:40 amIAD - MCO
Nonstop2h 25mFrontier
Deal found 11/12$73
This Priceline deal was found by Cheapflights users on 11/12. 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.
Sat 12/66:34 pmMCO - BWI
1 stop5h 11mMultiple Airlines
Sun 12/78:13 amBWI - MCO
Nonstop2h 39mMultiple Airlines
Deal found 11/12$73
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/56:08 pmMCO - IAD
Nonstop2h 16mMultiple Airlines
Mon 12/153:50 pmIAD - MCO
1 stop4h 05mMultiple Airlines
Deal found 11/12$74
This Frontier deal was found by Cheapflights users on 11/13. 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.
Mon 11/241:04 pmMCO - BWI
Nonstop2h 16mFrontier
Thu 11/274:25 pmBWI - MCO
Nonstop2h 35mFrontier
Deal found 11/13$74
This Priceline deal was found by Cheapflights users on 11/11. 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.
Thu 12/46:06 pmMCO - PHL
Nonstop2h 33mMultiple Airlines
Tue 12/95:30 amPHL - MCO
Nonstop2h 44mMultiple Airlines
Deal found 11/11$74
This Priceline deal was found by Cheapflights users on 11/12. 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.
Thu 12/1110:05 pmMCO - BWI
Nonstop2h 18mMultiple Airlines
Thu 12/188:17 amBWI - MCO
Nonstop2h 39mMultiple Airlines
Deal found 11/12$75
This Frontier deal was found by Cheapflights users on 11/12. 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 11/2111:40 amMCO - PHL
Nonstop2h 34mFrontier
Fri 11/215:40 pmPHL - MCO
Nonstop2h 45mFrontier
Deal found 11/12$75
This Super.com deal was found by Cheapflights users on 11/12. 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.
Mon 11/245:31 amMCO - IAD
Nonstop2h 14mFrontier
Fri 11/288:35 amIAD - MCO
Nonstop2h 25mFrontier
Deal found 11/12$76
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Tue 11/253:05 pmMCO - BWI
Nonstop2h 19mMultiple Airlines
Thu 11/278:45 pmBWI - MCO
Nonstop2h 29mMultiple Airlines
Deal found 11/11$76

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 November 13, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$70
(Gotogate)

One-way from

$39
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$144
Provider with most accurate pricing for Orlando (ORL)-Washington, D.C. (WAS) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Washington, D.C. (WAS) flights.
Search Deals
From Kissimmee to Maryland
Search Deals
One-way flight from Kissimmee to Maryland
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 13, 2025.
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

Thu 11/27

8:48 am-11:20 am

Nonstop2h 32m

Philadelphia

Sat 11/29

5:01 am-7:38 am

Nonstop2h 37m

$79

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Fri 1/30

9:01 pm-11:17 pm

Nonstop2h 16m

Baltimore/Washington

Sun 2/1

12:18 pm-11:54 pm

1 stop11h 36m

$79

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Mon 12/29

5:05 am-7:22 am

Nonstop2h 17m

Baltimore/Washington

Mon 1/5

10:00 pm-12:37 am

Nonstop2h 37m

$85

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Fri 11/21

6:00 am-8:23 am

Nonstop2h 23m

Baltimore/Washington

Fri 11/28

7:30 am-9:59 am

Nonstop2h 29m

$86

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Thu 12/11

12:57 pm-12:24 am

1 stop11h 27m

Baltimore/Washington

Fri 12/12

9:11 pm-11:47 pm

Nonstop2h 36m

$86

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 11/22

3:05 pm-5:24 pm

Nonstop2h 19m

Baltimore/Washington

Sat 11/29

7:30 am-9:59 am

Nonstop2h 29m

$93

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 12/6

6:34 pm-11:45 pm

1 stop5h 11m

Baltimore/Washington

Tue 12/9

6:30 am-1:24 pm

1 stop6h 54m

$97

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Tue 11/25

11:04 am-1:21 pm

Nonstop2h 17m

Baltimore/Washington

Thu 11/27

6:38 pm-11:25 pm

1 stop4h 47m

$97

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sun 12/7

5:01 am-7:18 am

Nonstop2h 17m

Baltimore/Washington

Fri 12/12

9:11 pm-11:47 pm

Nonstop2h 36m

$100

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Tue 11/25

3:05 pm-5:24 pm

Nonstop2h 19m

Baltimore/Washington

Fri 11/28

7:30 am-9:59 am

Nonstop2h 29m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

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 $34). 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 November 13, 2025.

It’s typically best to fly out from Kissimmee to Maryland in the afternoon. Doing so could potentially save you 37% on the flight price compared to flying at noon, 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 November 2, 2025.

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

Weekly flight availability from Kissimmee to Maryland

Explore weekly flight availability from Kissimmee to Maryland. 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 November 13, 2025.

The most flights from K1S to USMD are scheduled on a Thursday (23 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

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 November 13, 2025.
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
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
8,139 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
5.8
Fair
3,109 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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 12m. Airlines will cover a distance of 759 mi. Generally, flights for this route are nonstop.

  • 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 $49 on Breeze Airways. Other airlines that offer cheap prices include Spirit Airlines from $49 and United Airlines from $54 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 Spirit Airlines (86%), Frontier (81%) or Southwest (76%) 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 $135 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 $66.

  • 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 $34). 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.

See more FAQs

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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$56Average$151FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$74Average$147FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$108Average$164FlexibilityNo cancel feeOn-time88%
DeltaCheapest$147Average$422FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$188Average$308FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$200Average$472FlexibilityNo cancel feeOn-time71%

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