$29 Cheap Flights to Chestertown , MD

Bundle Your Flight + Hotel & Save!

Featured airlines

Featured Airlines: American Airlines, United Airlines, Delta, Spirit, JetBlue, Frontier, Air India, Hawaiian Airlines and Qatar Airways

    Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash

How much is the cheapest flight to Chestertown?

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.

American Airlines
American Airlines
American Airlines
American Airlines
American Airlines

Find Your Flights to Chestertown BWI

Cheap flights to Chestertown (BWI)

Get started finding a cheap flight to Chestertown 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.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Chestertown.

Roundtrip prices range from $58 - $387, and one-ways to Chestertown start as low as $29.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

Airlines that fly to Chestertown (BWI)

You have several options for which airline you choose to travel with to Chestertown. There are 10 airlines flying into BWI: American Airlines. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check a bag or bring a carry-on, check whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked/carry-on baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programs may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel in one online platform.

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at the optimal times. Airfare to Chestertown (BWI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to BWI in August and in May for one-ways.

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24-hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

Where can I learn more about changing or canceling my flight to Chestertown?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
How do I find cheap flights to Chestertown that have flexible change policies?
We understand that things can change in a flash, so choosing a flexible airfare with Expedia is always a wise idea. Simply mark the “No change fee” box underneath the “Flexible change policies” filter. Your low-cost, flexible flight to Chestertown is just a few clicks away.
What is the name of Chestertown's airport?
If you’re traveling by plane, you won’t have to decide which airport to fly into. Chestertown has just one – Baltimore Washington Intl. Thurgood Marshall Airport (BWI).
What airport is best to fly into Chestertown?
With only one main airport operating in Chestertown, it won’t take much time to find the best flight. You’ll be jetting off to BWI Airport, which sits around 30 mi from the center of town.
How many airlines fly to Chestertown?
There are a total of 18 air carriers connecting Chestertown with 77 airports from all over the globe.
How many nonstop flights are there to Chestertown?
Flying to a new place is much easier when there aren’t any stopovers to slow you down. If you’re heading to Chestertown, the great news is that there are around 2,050 direct flights each week.
Where are the most popular flights to Chestertown departing from?
Travelers often jet off from Atlanta, Orlando and Chicago airports when heading to Chestertown.
How long is the flight to Chestertown Airport?
Which city you depart from determines how much of the in-flight entertainment you’ll get to enjoy. From Atlanta to Chestertown, the average flight time is 1 hour and 47 minutes. From Chicago it’s more like 1 hour and 49 minutes, and from Orlando it’s 2 hours and 11 minutes.
How to book the cheapest flight to Chestertown?
If you’d like to save some cash on your Chestertown vacation, then listen up! As every experienced traveler will tell you, avoid booking at the last minute. Fares are usually more expensive close to the departure date. Don’t stop there, though. Do some research and check if there is more than one airport at your destination. Fares often differ depending on which airport you go for. Don’t forget to compare prices across air carriers as well. Finally, be ready to book quickly if you find an irresistible price. It might not stick around for long. With a bit of know-how and some good fortune, the ideal fare can be yours.
How to survive the flight to Chestertown?
Depending on where you’re coming from, your journey to Chestertown could be a piece of cake or it could drag on forever. Here are some tips that will help you start your next great adventure on a positive note.What to pack in your hand luggage:

  • The secret to having a hassle-free travel experience is to pack in advance. So, let’s start with the essentials: passport, official ID, bank cards and daily medications. Next, bring items that’ll help keep you occupied, like your laptop or a few magazines. It’s also a wise idea to bring your chargers, a quality neck pillow and a pair of earplugs. Finally, don’t forget to toss in toiletry items like a toothbrush, deodorant and a clean T-shirt.

Do not pack the following items in your hand luggage:

  • Double-check that you don’t have a pocket knife hiding in your carry-on luggage. Other banned items include explosive or flammable substances, like aerosols and matches, and gels and liquids in containers with a volume of more than 3.4 ounces (100 milliliters).

What to wear on a flight:

  • Comfort should be your highest priority when selecting what to wear on board. Consider your choice of footwear with care too, as swollen feet and ankles are a common side effect of flying. Slightly roomy, flat shoes are your best bet.
  • Unfortunately, a risk of flying long distances is developing deep vein thrombosis (DVT), a blood clot condition caused by prolonged periods of inactivity. To avoid this, take every opportunity to walk around and give your legs a stretch. Compression tights and socks are also a great idea to help lower your risk.

How to get through airport security fast when flying to Chestertown?
It’s simple — be prepared. We’ve rounded up some handy tips and tricks for a stress-free trip through airport security. Look out Chestertown, here you come:

  • Security personnel first need to know that you have a valid ID and matching boarding pass before you can proceed any further. Have them ready for inspection.
  • The X-ray machine comes next. Empty your pockets and remove anything that is likely to set off the alarm. This includes things like headphones or earphones, as well as your coat or jacket. They’ll need to be placed on the conveyor belt for screening.
  • All your electronics, including your phone and laptop, are also required to be separately scanned.
  • Any gels or liquids, such as perfume or hairspray, that you want to bring on board must be no greater than 3.4 ounces (100 milliliters). They must also all fit inside a quart-size (one liter), clear zip-close bag.
  • Lightweight sneakers are a clever footwear choice as you’re less likely to be asked to remove them when passing through security. Hiking boots and other heavy-style shoes are usually subjected to additional screening.
  • Sharp or pointed objects (like knives and scissors) are prohibited in the cabin. They’ll be confiscated at security, so pack them in your checked luggage.

Flights to Chestertown information
Destination airport
Salisbury - Ocean City Wicomico Regional
Destination airport IATA code
SBY
Destination city name
Salisbury
Roundtrip price
$366

Trending flights to Chestertown

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
*Available to One Key members.