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$51+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — BWI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$93
(FlightHub)

One-way from

$51
(Frontier)

Popular in

December

Cheapest in

February

Average price

$152
From Kissimmee to Maryland
Search Deals
One-way flight from Kissimmee to Maryland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/105:22 pmMCO - IAD
Nonstop2h 11mFrontier
Sun 10/128:18 pmIAD - MCO
Nonstop2h 21mFrontier
Deal found 7/30$93
This FlightHub deal was found by Cheapflights users on 7/28. 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.
Wed 8/139:22 amMCO - BWI
Nonstop2h 22mSpirit Airlines
Mon 8/189:57 pmBWI - MCO
Nonstop2h 18mSpirit Airlines
Deal found 7/28$102
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 8/75:30 amMCO - PHL
Nonstop2h 32mFrontier
Mon 8/1110:29 pmPHL - MCO
Nonstop2h 34mFrontier
Deal found 7/29$103
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/91:17 pmMCO - BWI
Nonstop2h 29mFrontier
Sat 8/162:59 pmBWI - MCO
Nonstop2h 36mFrontier
Deal found 7/28$103
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/315:35 amMCO - PHL
Nonstop2h 29mSpirit Airlines
Wed 8/133:46 pmPHL - MCO
Nonstop2h 35mSpirit Airlines
Deal found 7/28$107
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2012:10 pmMCO - PHL
Nonstop2h 28mMultiple Airlines
Sat 8/238:02 pmPHL - MCO
Nonstop2h 51mMultiple Airlines
Deal found 7/30$109
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 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 24mMultiple Airlines
Sat 10/189:54 pmBWI - MCO
Nonstop2h 24mMultiple Airlines
Deal found 7/28$110
This Breeze Airways deal was found by Cheapflights users on 7/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:07 pmMCO - SBY
Nonstop2h 15mBreeze Airways
Mon 11/38:02 pmSBY - MCO
Nonstop2h 15mBreeze Airways
Deal found 7/29$118
This Flysmarter deal was found by Cheapflights users on 7/29. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/212:35 pmMCO - DCA
Nonstop2h 21mJetBlue
Sun 8/247:40 amDCA - MCO
Nonstop2h 22mJetBlue
Deal found 7/29$126
This Delta deal was found by Cheapflights users on 7/30. 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.
Tue 10/2810:35 amMCO - DCA
Nonstop2h 07mDelta
Tue 11/42:00 pmDCA - MCO
Nonstop2h 20mDelta
Deal found 7/30$127
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/28:00 amMCO - IAD
Nonstop2h 11mUnited Airlines
Wed 9/312:35 pmIAD - MCO
Nonstop2h 22mUnited Airlines
Deal found 7/28$132
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 8/2011:45 amMCO - DCA
Nonstop2h 14mAmerican Airlines
Wed 8/205:34 pmDCA - MCO
Nonstop2h 32mAmerican Airlines
Deal found 7/29$134

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 July 30, 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

OrlandoWashington, D.C.

MCO - IAD

MCOIAD

Orlando

Fri 10/10

5:22 pm-7:33 pm

Nonstop2h 11m

Washington, D.C. Dulles Intl

Sun 10/12

8:18 pm-10:39 pm

Nonstop2h 21m

$93

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Wed 8/13

9:22 am-11:44 am

Nonstop2h 22m

Baltimore/Washington

Mon 8/18

9:57 pm-12:15 am

Nonstop2h 18m

$102

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Sat 8/9

1:17 pm-3:46 pm

Nonstop2h 29m

Baltimore/Washington

Sat 8/16

2:59 pm-5:35 pm

Nonstop2h 36m

$103

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Thu 8/7

5:30 am-8:02 am

Nonstop2h 32m

Philadelphia

Mon 8/11

10:29 pm-1:03 am

Nonstop2h 34m

$103

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Wed 8/20

12:10 pm-2:38 pm

Nonstop2h 28m

Philadelphia

Sat 8/23

8:02 pm-10:53 pm

Nonstop2h 51m

$109

OrlandoBaltimore

MCO - BWI

MCOBWI

Orlando

Wed 10/1

1:05 pm-3:29 pm

Nonstop2h 24m

Baltimore/Washington

Sat 10/18

9:54 pm-12:18 am

Nonstop2h 24m

$110

OrlandoPhiladelphia

MCO - PHL

MCOPHL

Orlando

Tue 8/19

10:34 am-1:01 pm

Nonstop2h 27m

Philadelphia

Sun 8/24

9:59 pm-12:29 am

Nonstop2h 30m

$111

OrlandoWashington, D.C.

MCO - DCA

MCODCA

Orlando

Thu 8/21

2:35 pm-4:56 pm

Nonstop2h 21m

Washington, D.C. Reagan-National

Sun 8/24

7:40 am-10:02 am

Nonstop2h 22m

$126

OrlandoWashington, D.C.

MCO - DCA

MCODCA

Orlando

Tue 10/28

10:35 am-12:42 pm

Nonstop2h 07m

Washington, D.C. Reagan-National

Tue 11/4

2:00 pm-4:20 pm

Nonstop2h 20m

$127

OrlandoWashington, D.C.

MCO - IAD

MCOIAD

Orlando

Tue 9/2

8:00 am-10:11 am

Nonstop2h 11m

Washington, D.C. Dulles Intl

Wed 9/3

12:35 pm-2:57 pm

Nonstop2h 22m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 34 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 July 30, 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 July 30, 2025.

The most flights from K1S to USMD are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, 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 July 30, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Breeze Airways
8.0
Very good
191 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

8.0

Food

7.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 $51 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $52 and Breeze Airways from $61 one-way.

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

    While some choose either Orlando - Washington, D.C. Dulles Intl or Orlando - Washington, D.C. Reagan-National, Orlando - Baltimore/Washington 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 (80%), Spirit Airlines (71%) 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 $126 for a flight from Kissimmee to Maryland. The cheapest flight overall is $50 while the most popular route, (Orlando - Baltimore/Washington) is currently priced at $84.

  • 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$55Average$147FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$59Average$140FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$101Average$146FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$147Average$263FlexibilityNo cancel feeOn-time69%
DeltaCheapest$147Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$180Average$477FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$199Average$315FlexibilityNo cancel feeOn-time63%

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