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$48+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BWI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$80
(Booking.com)

One-way from

$48
(FlightHub)

Popular in

December

Cheapest in

February

Average price

$142
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. 10% potential increase in price ($17 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 May 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 May 1, 2025.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:30 amMCO - PHL
Nonstop2h 32mFrontier
Sun 8/1010:29 pmPHL - MCO
Nonstop2h 36mFrontier
Deal found 4/30$80
This FlightHub deal was found by Cheapflights users on 4/28. 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.
Fri 5/25:01 pmMCO - PHL
Nonstop2h 35mSpirit Airlines
Mon 5/511:40 amPHL - MCO
Nonstop2h 45mSpirit Airlines
Deal found 4/28$86
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:09 pmMCO - BWI
Nonstop2h 20mSpirit Airlines
Sat 5/2412:51 pmBWI - MCO
Nonstop2h 23mSpirit Airlines
Deal found 4/30$87
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/610:31 amMCO - IAD
Nonstop2h 18mFrontier
Mon 6/91:34 pmIAD - MCO
Nonstop2h 23mFrontier
Deal found 4/30$88
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:20 amMCO - PHL
Nonstop2h 28mMultiple Airlines
Sun 5/1110:59 pmPHL - MCO
Nonstop2h 25mMultiple Airlines
Deal found 4/30$91
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/712:30 pmMCO - BWI
Nonstop2h 25mMultiple Airlines
Tue 5/138:26 amBWI - MCO
Nonstop2h 26mMultiple Airlines
Deal found 4/30$95
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/319:45 amMCO - BWI
Nonstop2h 25mFrontier
Sat 5/312:19 pmBWI - MCO
Nonstop2h 27mFrontier
Deal found 4/30$97
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2910:15 amMCO - IAD
Nonstop2h 17mMultiple Airlines
Sun 6/111:54 amIAD - MCO
1 stop25h 09mMultiple Airlines
Deal found 4/30$152
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/107:04 amMCO - DCA
Nonstop2h 20mAmerican Airlines
Tue 6/1011:55 amDCA - MCO
Nonstop2h 17mAmerican Airlines
Deal found 4/30$152
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/63:44 pmMCO - DCA
Nonstop2h 16mJetBlue
Sun 6/88:20 amDCA - MCO
Nonstop2h 32mJetBlue
Deal found 4/30$157
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2210:20 amMCO - DCA
Nonstop2h 17mDelta
Tue 5/272:59 pmDCA - MCO
Nonstop2h 21mDelta
Deal found 4/30$167
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/3011:35 amMCO - IAD
1 stop8h 42mAvelo Airlines
Fri 6/69:05 pmIAD - MCO
1 stop20h 20mAvelo Airlines
Deal found 4/30$174

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 May 1, 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 5/29

7:59 pm-10:36 pm

Nonstop2h 37m

Philadelphia

Sun 6/1

7:12 pm-9:54 pm

Nonstop2h 42m

$80

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Thu 7/17

5:30 am-8:02 am

Nonstop2h 32m

Philadelphia

Mon 7/21

6:42 pm-9:37 pm

Nonstop2h 55m

$81

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Wed 5/21

6:09 pm-8:29 pm

Nonstop2h 20m

Baltimore/Washington

Sat 5/24

12:51 pm-3:14 pm

Nonstop2h 23m

$87

OrlandoWashington, D.C.

MCO - IAD

MCOIAD

Orlando

Fri 6/6

10:31 am-12:49 pm

Nonstop2h 18m

Washington, D.C. Dulles Intl

Mon 6/9

1:34 pm-3:57 pm

Nonstop2h 23m

$88

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Thu 5/8

5:20 am-7:48 am

Nonstop2h 28m

Philadelphia

Sun 5/11

10:59 pm-1:24 am

Nonstop2h 25m

$91

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 6/7

9:31 am-11:46 am

Nonstop2h 15m

Baltimore/Washington

Mon 6/9

12:23 pm-2:47 pm

Nonstop2h 24m

$96

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 5/31

9:45 am-12:10 pm

Nonstop2h 25m

Baltimore/Washington

Sat 5/31

2:19 pm-4:46 pm

Nonstop2h 27m

$97

OrlandoWashington, D.C.

MCO - DCA

MCODCA

Orlando

Tue 6/10

7:04 am-9:24 am

Nonstop2h 20m

Washington, D.C. Reagan-National

Tue 6/10

11:55 am-2:12 pm

Nonstop2h 17m

$152

OrlandoWashington, D.C.

MCO - IAD

MCOIAD

Orlando

Thu 5/29

10:15 am-12:32 pm

Nonstop2h 17m

Washington, D.C. Dulles Intl

Sun 6/1

11:54 am-1:03 pm

1 stop25h 09m

$152

OrlandoWashington, D.C.

MCO - DCA

MCODCA

Orlando

Fri 6/6

3:44 pm-6:00 pm

Nonstop2h 16m

Washington, D.C. Reagan-National

Sun 6/8

8:20 am-10:52 am

Nonstop2h 32m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 52 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 May 1, 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 May 1, 2025.

The most flights from K1S to USMD are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Maryland by month

Plan your trip to Maryland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maryland ranges from 2.9 - 4.1 inches per month. July is typically the wettest month, when rainfall can reach 4.1 in. February is typically the driest time to visit Maryland when rainfall is around 2.9 in.

Temperature in Maryland by month

Plan your trip to Maryland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maryland, 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 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

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 May 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Kissimmee to Maryland have to say. 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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

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 Kissimmee to Maryland. 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 Kissimmee to Maryland one-way?

    One-way options have recently been found by users for as low as $48 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $50 and Delta from $79 one-way.

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

    While some choose either Orlando - Baltimore/Washington or Orlando - Washington, D.C. Dulles Intl, Orlando - Philadelphia 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 Southwest (79%), Spirit Airlines (73%) or Frontier (73%) 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 $144 for a flight from Kissimmee to Maryland. The cheapest flight overall is $53 while the most popular route, (Orlando - Philadelphia) is currently priced at $71.

  • 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$52Average$136FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$55Average$133FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$107Average$145FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$131Average$217FlexibilityNo cancel feeOn-time62%
DeltaCheapest$147Average$379FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$198Average$332FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$206Average$487FlexibilityNo cancel feeOn-time71%

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