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$49+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BWI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$71
(Cheapflightsfares)

One-way from

$49
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$124
From Kissimmee to Maryland
Search Deals
One-way flight from Kissimmee to Maryland
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/810:21 amMCO - BWI
Nonstop2h 19mSpirit Airlines
Sat 10/119:00 pmBWI - MCO
Nonstop2h 24mSpirit Airlines
Deal found 9/15$71
This CheapOair deal was found by Cheapflights users on 9/15. 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 10/11:05 pmMCO - BWI
Nonstop2h 24mFrontier
Mon 10/64:09 pmBWI - MCO
Nonstop2h 34mFrontier
Deal found 9/15$72
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/164:43 pmMCO - IAD
Nonstop2h 24mFrontier
Fri 10/179:28 pmIAD - MCO
Nonstop2h 21mFrontier
Deal found 9/15$73
This Frontier deal was found by Cheapflights users on 9/15. 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 10/234:43 pmMCO - IAD
Nonstop2h 24mFrontier
Mon 10/2710:33 pmIAD - MCO
Nonstop2h 21mFrontier
Deal found 9/15$74
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:13 pmMCO - BWI
Nonstop2h 19mSpirit Airlines
Sat 10/184:20 pmBWI - MCO
Nonstop2h 21mSpirit Airlines
Deal found 9/15$74
This Priceline deal was found by Cheapflights users on 9/15. 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 10/106:10 amMCO - BWI
Nonstop2h 24mMultiple Airlines
Sun 10/126:53 amBWI - MCO
Nonstop2h 22mMultiple Airlines
Deal found 9/15$76
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/11:05 pmMCO - BWI
Nonstop2h 24mFrontier
Sat 10/44:24 pmBWI - MCO
Nonstop2h 34mFrontier
Deal found 9/17$77
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:49 amMCO - BWI
Nonstop2h 17mFrontier
Sun 12/143:01 pmBWI - MCO
Nonstop2h 33mFrontier
Deal found 9/17$78
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 9/271:05 pmMCO - BWI
Nonstop2h 24mFrontier
Sun 9/289:27 pmBWI - MCO
Nonstop2h 32mFrontier
Deal found 9/17$79
This CheapOair deal was found by Cheapflights users on 9/15. 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 10/1510:21 amMCO - BWI
Nonstop2h 19mSpirit Airlines
Wed 10/228:00 amBWI - MCO
Nonstop2h 22mSpirit Airlines
Deal found 9/15$80
This Priceline deal was found by Cheapflights users on 9/14. 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 10/210:35 amMCO - PHL
Nonstop2h 27mMultiple Airlines
Mon 10/65:15 amPHL - MCO
Nonstop2h 41mMultiple Airlines
Deal found 9/14$80
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/24:00 pmMCO - IAD
Nonstop2h 24mFrontier
Sun 10/57:14 pmIAD - MCO
Nonstop2h 32mFrontier
Deal found 9/15$81

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 September 17, 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

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 11/1

7:00 am-9:21 am

Nonstop2h 21m

Baltimore/Washington

Sat 11/8

9:37 pm-12:01 am

Nonstop2h 24m

$77

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Thu 10/30

10:21 am-12:40 pm

Nonstop2h 19m

Baltimore/Washington

Sun 11/2

8:30 pm-10:54 pm

Nonstop2h 24m

$80

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Tue 10/7

11:44 am-2:17 pm

Nonstop2h 33m

Philadelphia

Tue 10/14

8:00 am-10:34 am

Nonstop2h 34m

$85

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Wed 10/15

10:30 am-12:53 pm

Nonstop2h 23m

Philadelphia

Sat 10/18

11:30 am-2:09 pm

Nonstop2h 39m

$86

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 9/27

1:13 pm-3:32 pm

Nonstop2h 19m

Baltimore/Washington

Sun 9/28

8:52 pm-11:17 pm

Nonstop2h 25m

$86

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Wed 10/15

10:21 am-12:40 pm

Nonstop2h 19m

Baltimore/Washington

Sun 10/19

8:30 pm-10:54 pm

Nonstop2h 24m

$99

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Thu 10/9

10:48 pm-1:13 am

Nonstop2h 25m

Philadelphia

Mon 10/13

6:18 am-2:33 pm

1 stop8h 15m

$105

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Mon 10/27

6:06 am-11:54 am

1 stop5h 48m

Baltimore/Washington

Wed 10/29

8:00 am-10:22 am

Nonstop2h 22m

$105

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Tue 10/21

1:03 pm-8:23 pm

1 stop7h 20m

Baltimore/Washington

Sat 10/25

9:00 pm-11:24 pm

Nonstop2h 24m

$105

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 11/8

9:30 pm-9:53 am

1 stop12h 23m

Baltimore/Washington

Tue 11/11

9:37 pm-12:01 am

Nonstop2h 24m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

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, August is the cheapest month in which you can book a flight from Kissimmee to Maryland (average of $241). Flying from Kissimmee to Maryland in March is currently the most expensive (average of $290). 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 September 17, 2025.

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

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 September 17, 2025.

The most flights from K1S to USMD are scheduled on a Monday (17 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 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 September 17, 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

Boarding

8.1

Food

7.0

Crew

8.6

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

Boarding

8.1

Food

7.0

Crew

8.6

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
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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 15m. Airlines will cover a distance of 761 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 $50 on Spirit Airlines. Other airlines that offer cheap prices include Breeze Airways from $59 and United Airlines from $66 one-way.

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

    While some choose either Orlando - Baltimore/Washington or Orlando - Washington, D.C. Reagan-National, 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 (78%), Southwest (74%) or Spirit Airlines (62%) 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 $199 for a flight from Kissimmee to Maryland. The cheapest flight overall is $43 while the most popular route, (Orlando - Washington, D.C. Dulles Intl) is currently priced at $73.

  • 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, August is the cheapest month in which you can book a flight from Kissimmee to Maryland (average of $241). Flying from Kissimmee to Maryland in March is currently the most expensive (average of $290). 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 Kissimmee to Maryland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Kissimmee to Maryland

Discover the top 7 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$150FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$145FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$108Average$158FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$147Average$263FlexibilityNo cancel feeOn-time69%
DeltaCheapest$147Average$397FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$180Average$501FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$197Average$311FlexibilityNo cancel feeOn-time63%

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