$22 Cheap Flights to Leonardtown, MD

Flights to Leonardtown at a glance

Booking your flight to Leonardtown is a breeze. You can choose from a variety of options, including both full-service and cheap flights to Leonardtown. Simply compare travel times and select the best choice that fits your budget and schedule while planning to explore the city's renowned sights and neighborhoods.

• Major airport near Leonardtown: Ronald Reagan Washington National Airport (DCA)
• Flights per week: 4,300+ flights arriving at Leonardtown airport
• Number of airlines that fly to Leonardtown: around 40+ carriers

Popular airport near Leonardtown

Leonardtown is a charming city perfect for those seeking outdoor adventures, scenic views, and beach getaways. Its romantic atmosphere and opportunities for adventure draw many visitors. Travelers can conveniently access the area through major airports nearby, making it easy to plan your trip to Leonardtown, Maryland.

• Ronald Reagan Washington National Airport (DCA): Situated in Arlington County, Virginia, approximately 44 miles from Leonardtown, this airport offers a wide range of domestic and international flights. It connects to over 225 domestic cities and more than 115 international locations. Passengers can opt for enhanced comfort by selecting first class, premium economy, or business class seating based on their chosen airline and route. Key airlines operating at this airport include American Airlines, Delta, and JetBlue Airways.

Top routes to Leonardtown

• Boston (BOS) to Leonardtown (DCA), with one-way flights starting at around $70
• Orlando (MCO) to Leonardtown (DCA), with one-way fares starting at around $55
• Miami (MIA) to Leonardtown (DCA), with one-way tickets available from around $65
• Los Angeles (LAX) to Leonardtown (DCA), with one-way fares starting at around $110
• Fort Lauderdale (FLL) to Leonardtown (DCA), with one-way airfare from around $60

Cheapest routes to Leonardtown

• Orlando (MCO) to Leonardtown (DCA), with budget one-way fares from around $55
• New York (JFK/LGA) to Leonardtown (DCA), with affordable one-way prices from around $55
• Denver (DEN) to Leonardtown (DCA), with budget one-way fares from around $55
• Fort Lauderdale (FLL) to Leonardtown (DCA), with budget one-way fares from around $60
• Newark (EWR) to Leonardtown (DCA), with cheap one-way fares from around $60

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Leonardtown

• American Airlines: Operating flights to Ronald Reagan Washington National Airport (DCA), this airline represents about 48% of arrivals in Leonardtown. Average one-way fares hover around $300, with premium service options that may include business and first class, depending on the route.
• Delta: Also servicing Ronald Reagan Washington National Airport (DCA), Delta handles roughly 17% of arrivals in Leonardtown. The average fare for a one-way ticket is about $290, featuring premium service possibilities such as premium economy, business, and first class based on the route.
• Southwest Airlines: With routes to Ronald Reagan Washington National Airport (DCA), Southwest Airlines accounts for approximately 11% of arrivals in Leonardtown. The typical one-way fare is around $230, making it a popular choice for budget-conscious travelers.
• United: Serving Ronald Reagan Washington National Airport (DCA), United comprises about 10% of arrivals to Leonardtown. The average one-way fare is close to $320, with first-class service available as a premium option depending on the specific route.
• JetBlue Airways: Flying into Ronald Reagan Washington National Airport (DCA), JetBlue handles around 7% of arrivals in Leonardtown. One-way fares average approximately $260, and premium service may include premium economy depending on the route taken.

Best time to fly to Leonardtown

The most popular months for travelers to fly to Leonardtown are January, March, and April, when peak temperatures in Leonardtown can reach up to 56.1°F in April. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 71.1°F. For better deals, May usually offers the lowest average one-way fare around $195, roughly 7% cheaper than the yearly average. Looking for additional cheaper months to fly? October, September, and August offer average one-way fares of around $200, making them good options for flexible travelers.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Leonardtown

Getting some of the best deals on flights to Leonardtown is all about timing and flexibility. Here are some key tips to help you save:

1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
3. Bundle and save—book a flight and unlock a hotel deal on Expedia.*
4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
5. Earn miles—you can earn airline miles when you book your Leonardtown flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Leonardtown

Leonardtown welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Leonardtown efficiently:

• Public transportation: From Ronald Reagan Washington National Airport, National Airport Station (a metro station) is conveniently located about 0.2 miles away by walking, while Alexandria Station (a train station) is approximately 3.8 miles away by car, and Washington Seaport (a seaport) is about 4.8 miles away by car, providing easy access to various transportation options for travelers.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Leonardtown, with private rides that can be arranged in advance.
• Car rental: Renting a car in Leonardtown is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Leonardtown on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Leonardtown

• Lexington Park: Located 10 miles drive away from Leonardtown, Lexington Park is a vibrant city that invites travelers to enjoy its scenic outdoor spaces and rich cultural experiences. Here, you can explore the historic St. Mary's College of Maryland and the charming Historic St. Mary's City, both perfect for immersing yourself in local history. For those seeking recreation, the Michael P. O'Brien Athletics and Recreation Center offers various activities, while the nearby bay provides picturesque views and opportunities for relaxation.
• Lusby: Lusby is located 15 miles drive away from Leonardtown and is an excellent destination for outdoor enthusiasts and adventure seekers. The area boasts stunning natural landmarks, including the dramatic cliffs at Calvert Cliffs State Park and the serene beach at Cove Point Lighthouse. Additionally, Jefferson Patterson Park and Museum offers a blend of outdoor activities and educational experiences, making Lusby a great spot for both relaxation and exploration.
• Hollywood: Situated 6 miles drive away from Leonardtown, Hollywood offers a delightful mix of outdoor activities and beautiful scenery. The area is home to the impressive Calvert Cliffs State Park, perfect for hiking and enjoying nature. Another highlight is the Jefferson Patterson Park and Museum, which provides educational opportunities in a stunning outdoor setting. Broad Creek Community Park is an ideal family-friendly spot for leisurely walks and picnics, ensuring a memorable visit for everyone.

Tips for short-haul flights to Leonardtown

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

• Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often more economical. Maximize space by bringing mini toiletries, wearing your bulkiest clothes, and planning your outfits carefully. This approach also allows you to bypass the wait at baggage claim once you arrive.
• Bring your own entertainment—many short-haul flights may not provide in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself entertained. Be sure to fully charge your devices before you board.
• Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to arrive at least 1.5 to 2 hours before departure, taking into account potential traffic and security lines.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Leonardtown

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

• Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines typically allow free seat selection once online check-in opens, which is usually 24–48 hours prior to your flight. Some airlines may permit seat selection even earlier.
• Arrive at the airport in plenty of time—make sure to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
• Relax at the airport—if you have some extra time, take the opportunity to browse the shops, find a coffee shop, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
• Adjust to the new time zone mid-flight—begin synchronizing your body clock by changing your watch and sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Leonardtown

The cheapest day to fly

Get started finding a cheap flight to Leonardtown on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

October is the cheapest month to fly to Leonardtown. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Leonardtown. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Leonardtown, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Leonardtown

The lowest price for round-trip flights to Leonardtown in 2026 starts from $44, while one-way tickets start from from $22. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Leonardtown. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Leonardtown

Frontier Airlines, American Airlines, Southwest Airlines, United, Delta are just some of the airlines that can typically offer cheap tickets to Leonardtown. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Leonardtown and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Leonardtown, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Leonardtown. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Leonardtown plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Leonardtown

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Leonardtown.

Stopover savings

The cheapest tickets to Leonardtown are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Leonardtown. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Leonardtown for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Leonardtown. Simply download the free Expedia app to your smart device and activate Leonardtown flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Leonardtown. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.