$29 Cheap Flights to Chester, MD

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Popular airlines to Chester

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How much is the cheapest flight to Chester?

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Southwest Airlines
Delta
American Airlines
United

Alternative airports near Chester

Prices were available within the past 7 days. Prices and availability are subject to change.

What you need to know for your flight to Chester

Flights to Chester at a glance

Traveling to Chester is easy—simply select from a range of full-service or budget airlines, compare travel times, and choose the option that best fits your budget and itinerary as you plan to explore the city's renowned attractions and neighborhoods.

  • Major airport near Chester: Baltimore Washington International Thurgood Marshall Airport (BWI)
  • Flights per week: 3,350+ flights arriving at Chester airport
  • Number of airlines that fly to Chester: around 30+ carriers

Popular airport near Chester

Chester is a charming city perfect for outdoor enthusiasts and beach lovers alike. Visitors are drawn to its scenic beauty, family-friendly activities, and adventurous spirit. The city is conveniently served by a major airport, making travel easy for all explorers.

  • Baltimore Washington International Thurgood Marshall Airport (BWI): Situated in Anne Arundel County, Maryland, approximately 25 miles from Chester, this airport facilitates both domestic and international travel, linking to around 200 cities within the U.S. and over 120 destinations worldwide. Passengers can opt for enhanced comfort by selecting from first class, premium economy, or business class seating, depending on their chosen airline and route. Key airlines operating here include Southwest Airlines, Frontier Airlines, and American Airlines.

Top routes to Chester

  • Atlanta (ATL) to Chester (BWI), with one-way tickets available from around $35
  • Miami (MIA) to Chester (BWI), with one-way flight options from around $40
  • Chicago (ORD/MDW) to Chester (BWI), with one-way tickets available from around $50
  • Orlando (MCO) to Chester (BWI), with one-way airfare from around $35
  • Los Angeles (LAX) to Chester (BWI), with one-way tickets available from around $80

Cheapest routes to Chester

  • New Haven (HVN) to Chester (BWI), with cheap one-way fares from around $30
  • Fort Lauderdale (FLL) to Chester (BWI), with low one-way fares from around $35
  • Orlando (MCO) to Chester (BWI), with budget one-way fares from around $35
  • Atlanta (ATL) to Chester (BWI), with cheap one-way fares from around $35
  • Miami (MIA) to Chester (BWI), with budget one-way fares from around $40

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

Top airlines with flights to Chester

  • Southwest Airlines: Operating flights to Baltimore Washington International Thurgood Marshall Airport (BWI), Southwest Airlines represents roughly 36% of arrivals in Chester. Passengers can expect an average one-way fare of about $230.
  • American Airlines: With services to Baltimore Washington International Thurgood Marshall Airport (BWI), American Airlines accounts for approximately 20% of Chester's arrivals. The average one-way fare is around $320, with potential first-class service on select routes.
  • Delta: Serving Baltimore Washington International Thurgood Marshall Airport (BWI), Delta contributes about 20% of arrivals to Chester. The typical one-way fare is around $290, and premium cabin options may feature both premium economy and first-class service depending on the route.
  • United: Flying to Baltimore Washington International Thurgood Marshall Airport (BWI), United represents roughly 13% of arrivals in Chester. The average one-way fare stands at about $320, with first-class service available on certain routes.
  • Frontier Airlines: Offering flights to Baltimore Washington International Thurgood Marshall Airport (BWI), Frontier Airlines accounts for around 7% of Chester's arrivals. Travelers can find average one-way fares of approximately $160, making it a budget-friendly choice.

Best time to fly to Chester

The most popular months for travelers to fly to Chester are January, March, and April, when peak temperatures in Chester can reach up to 54.1°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 70.5°F and typically the lowest average one-way fare (around $203), roughly 9% cheaper than the yearly average. Looking for additional cheaper months to fly? October, May, and August offer average one-way fares of around $211, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January35.1°F (1.7°C)Light RainMostly SunnyModerately High$257
February37.4°F (3.0°C)Light RainMostly SunnyAverage$225
March43.9°F (6.6°C)Light RainMostly SunnyModerately High$239
April54.1°F (12.3°C)Light RainMostly SunnyModerately High$242
May63.5°F (17.5°C)Light RainMostly SunnyAverage$213
June72.3°F (22.4°C)Light RainMostly SunnyAverage$219
July77.9°F (25.5°C)Light RainMostly SunnyAverage$223
August76.3°F (24.6°C)Light RainMostly SunnyAverage$216
September70.5°F (21.4°C)Light RainMostly SunnyModerately Low$203
October60.3°F (15.7°C)Light RainMostly SunnyAverage$206
November48.7°F (9.3°C)Light RainMostly SunnyModerately Low$221
December41.0°F (5.0°C)Light RainMostly SunnyModerately Low$224

*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 Chester

Getting some of the best deals on flights to Chester 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*, or explore our Chester hotel and flight deals.
  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 Chester flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Chester

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

  • Public transportation: From Baltimore Washington International Thurgood Marshall Airport, BWI Thurgood Marshall Airport Metro Station (a metro station) is located about 0.3 miles from the airport and can be reached on foot, while Baltimore-Washington International Airport Station (a train station) is about 1.7 miles away and is most conveniently accessed by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chester, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Chester is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Chester 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 Chester

  • Stevensville: Located only 1 mile drive away from Chester, Stevensville is a charming city perfect for outdoor enthusiasts and beach lovers. The scenic views of the Chesapeake Bay and the inviting sandy shores of Sandy Point Beach make it an ideal spot for relaxation. Visitors can explore the expansive Sandy Point State Park, which offers a range of activities from hiking to picnicking. Don’t miss a stroll across the modern Chesapeake Bay Bridge, a local landmark that connects you to stunning vistas and experiences.
  • Grasonville: Grasonville is located 4 miles away from Chester and is a great destination for families seeking outdoor fun and beach activities. This vibrant city features a delightful boardwalk and a shopping center, making it both entertaining and convenient. Nearby attractions include the Chesapeake Bay Environmental Center, which emphasizes eco-friendly experiences, and the majestic Sandy Point State Park, where adventure awaits in the great outdoors. The iconic Chesapeake Bay Bridge also offers a striking backdrop for your travels.
  • Queenstown: Queenstown is located 7 miles away from Chester and is renowned for its family-friendly atmosphere and picturesque scenery. The city boasts excellent golf courses and shopping venues, making it a delightful place for leisure activities. Visitors can enjoy the beautiful landscapes near the Chesapeake Bay and explore the nearby Sandy Point State Park, where outdoor adventures abound. The Chesapeake Bay Environmental Center also offers educational opportunities and a unique experience for eco-conscious travelers.

Tips for short-haul flights to Chester

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

  • Pack light and skip checked bags—when flying with budget airlines, traveling with just a carry-on is often more economical. Maximize space by opting for mini toiletries, wearing your heaviest clothing, and coordinating outfits effectively. This strategy also allows you to bypass waiting at baggage claim upon arrival.
  • Bring your own entertainment—short-haul flights frequently lack in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself engaged. Remember to charge your devices fully before you board.
  • Arrive at the airport in plenty of time—for both short and domestic flights, it’s advisable to arrive at least 1.5 to 2 hours prior to departure, taking into account potential traffic and security delays.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Chester

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

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

Frequently asked questions

What month is the cheapest to fly to Chester?
Plan your trip for July if you want to get a deal on your fare. It's the cheapest month to fly to Chester. If possible, avoid traveling during peak periods such as public holidays or school breaks.
Which US cities have the cheapest flights to Chester?
Score cheap flights to Chester from Atlanta, Orlando and Chicago. These cities generally offer the best fares to this unique destination. But bear in mind that stopovers, seasonality and demand will also have an impact on rates, so remain flexible and book when prices are right.
Which US cities fly direct to Chester?
You can fly to Chester without a stopover from 65 US destinations. To find a nonstop journey, check "Direct flights only" when searching for flights to Chester on Expedia. Then, explore your choices and find the best departure out of any of these cities:

  • Atlanta
  • Orlando
  • Chicago
  • Fort Lauderdale
  • Boston

How to find a cheap flight to Chester?
To snag cheap flights to Chester, book early and consider traveling during the low season. Want a handy tip? Depart on a Thursday and you'll save 16% on average compared to those who travel on a Sunday.* Set up price tracking on the Expedia app and we'll let you know as soon as your fares drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Chester?
Although booking in advance is generally the best way to save cash, don't worry if your Chester trip is last minute. It's still possible to find cheap flights to Chester, especially if your plans have a little wiggle room. Try switching up your travel dates, exploring different ticket options or flying out of an alternative airport.
How far in advance should I book a flight to Chester?
Secure your flight to Chester two to four months ahead if you're flying in from an international destination. For domestic travel, the recommendation is around 28 days in advance. Cheaper tickets and a greater choice of travel dates, schedules and seating options are just some of the awesome benefits of booking early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Chester?
You can generally get cheap flights to Chester on a Sunday. You can save around 8% on average compared to those who book on a Friday, which is often the most expensive day to buy tickets.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Chester?
Chester has connections to 98 airports globally through 7 carriers, with Ronald Reagan Washington National Airport (DCA) as its primary entry point. Take your pick of these popular airlines to Chester when planning your trip:

  • JetBlue Airways
  • Delta Air Lines
  • American Airlines
  • United Airlines

Where do you fly into Chester?
Chester's main airport is Baltimore Washington Intl. Thurgood Marshall Airport (BWI). If you're looking for more nearby choices when flying to Chester, check out Ronald Reagan Washington National Airport (DCA), Salisbury - Ocean City Wicomico Regional Airport (SBY) or Annapolis, MD (ANP-Lee). It's also possible to fly to Chester through Easton, MD (ESN-Easton - Newnam).
How far is the airport from central Chester?
If you're arriving at Baltimore Washington Intl. Thurgood Marshall Airport (BWI), you'll be roughly 25 mi northwest of the center of Chester.
Can I save money by booking a Chester trip package?
You could possibly save hundreds of dollars if you secure a Chester flight and hotel package deal on Expedia. And you'll save yourself hassle by having all your travel plans in the same place. Try bundling flights and accommodations with add-ons like activities and tours for your own customized Chester vacation.
Can I change or cancel my flight to Chester?
It's often possible to change or cancel your flight to Chester. Many airlines let you cancel your flights for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may issue you credit for a future trip instead of a direct refund. To reserve affordable flights to Chester with flexible change policies, select "Changes included" or "No cancel fee" during your search. Looking for more information? Visit our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

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Travel information

Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Destination city name
Baltimore
Roundtrip price
$58

Trending flights to Chester

Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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