An aerial view of a town with a river, buildings, and surrounding greenery.

Cheap Flights to Chestertown

View NZ$283 flight on Tue, 1 Dec 2026Opens in a new window

Popular airlines to Chestertown

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 35% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Tickets to Chestertown

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Delta
American Airlines
United
Air New Zealand

Frequently asked questions

What is the name of Chestertown's airport?
If you're travelling by plane, you won't have to decide which airport to fly into. Chestertown has just one – Baltimore Washington Intl. Thurgood Marshall Airport (BWI).
How far is BWI from central Chestertown?
The journey from BWI to downtown Chestertown is reasonably long. You'll have to travel 48 kilometres before you can check in to your city hotel.
What airport is best to fly into Chestertown?
Travellers from across the globe go through BWI Airport each day. Step off the plane, grab your bags and you'll find yourself 48 kilometres from the heart of Chestertown.
How many airlines fly to Chestertown?
There are a total of 18 air carriers connecting Chestertown with 77 airports from all over the globe.
Which airlines fly to Chestertown?
Delta Air Lines, Southwest Airlines and Spirit Airlines are the most frequent fliers to Chestertown. The majority of flights come from Atlanta, with Delta Air Lines having the most services on this route.
How many nonstop flights are there to Chestertown?
With approximately 1 804 nonstop flights running every week, you'll be touching down in Chestertown before you can say, "Are we there yet?"
Where are the most popular flights to Chestertown departing from?
Flights to Chestertown from Atlanta, Boston and Fort Lauderdale airports are highly sought after.
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 holiday, then listen up! As every experienced traveller 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 litre), 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.

Book with confidence

Chestertown Flights

The Chestertown experience you’ve always wanted

Catching a flight to Chestertown is easier than it’s ever been when you use Expedia to plan your escape. A great holiday starts with great selection, and we have an amazing amount of Chestertown flight deals. A quick search on Expedia.co.nz will show you cheap tickets to Chestertown in mere moments, from overnight flights to weekend getaways. Trying to earn frequent flyer points? We even make it easy for you to stay loyal to your preferred airline.

Been a while since you’ve travelled?

If you haven’t flown recently, you might like some insider information. In fact, even seasoned travellers should check out our blog. Featuring hundreds of articles written by our very own experts, our blog keeps you informed about all the fantastic attractions and things to do in the world’s most popular destinations, so you know just what to pack. Get ready for great advice on trip preparation and seeing the sights—then get ready to fly!

Bundle your room and flight to travel for less

Package your flights with your hotel booking in Chestertown, and your trip will become even cheaper. By making all of your reservations with us, you’ll save money and time, plus have the peace of mind that comes with booking all of your arrangements in one place. It may seem like magic, but it’s just the Expedia.co.nz way.

A holiday at the tips of your fingers

Take the high-tech road when you use our Expedia app to plan your holiday to Chestertown. Our handy app allows you to reserve flights and hotels at any time of day, on any type of phone, because it’s available on both Android and iOS. You’ll also benefit from exclusive deals, have a chance to earn extra points, and can keep your itinerary at your fingertips. No matter where you are, count on our app to help you get where you’re going.

Register for Frequent Flyer Rewards

If you enjoy being pampered every once in a while, register with our Expedia Rewards program to get exclusive offers and discounts you won’t find anywhere else. Expedia Rewards grants you member-only benefits, plus price guarantees on your room rates. We can even help you rack up frequent flyer points more quickly. Plus, by signing up, you can book our Unreal Deals, which, when bundled with your room, could save you the cost of a whole plane ticket.

Start planning and start packing

Expedia.co.nz makes it easy to find cheap flights to Chestertown NZ$565. With such amazing deals, why wait any longer to book your trip? Start searching today, and we’ll see you soon in Chestertown.

Chestertown Flights

Travel information

Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Destination city name
Baltimore
Roundtrip price
NZ$564

Trending flights to Chestertown

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines

Explore a world of travel with Expedia

*Available to Expedia members.