S$115 Cheap Flights to Chestertown

View S$115 flight on Thu, 5 Feb, 2026Opens in a new window

Popular airlines to Chestertown

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Cheap round-trip 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.

Delta
Thu, 5 Feb - Thu, 12 Feb
ORD
Chicago
BWI
Baltimore
S$250 Return, found 1 day ago
S$250
Return
found 1 day ago
Select Delta flight, departing Thu, 5 Feb from Chicago to Baltimore, returning Thu, 12 Feb, priced at S$250 found 1 day ago
United
Thu, 15 Jan - Tue, 20 Jan
ORD
Chicago
BWI
Baltimore
S$262 Return, found 5 days ago
S$262
Return
found 5 days ago
Select United flight, departing Thu, 15 Jan from Chicago to Baltimore, returning Tue, 20 Jan, priced at S$262 found 5 days ago
American Airlines
Thu, 5 Feb - Thu, 12 Feb
ORD
Chicago
BWI
Baltimore
S$270 Return, found 1 day ago
S$270
Return
found 1 day ago
Select American Airlines flight, departing Thu, 5 Feb from Chicago to Baltimore, returning Thu, 12 Feb, priced at S$270 found 1 day ago
Swiss International Air Lines
Thu, 22 Jan - Mon, 26 Jan
LHR
London
BWI
Baltimore
S$825 Return, found 1 day ago
S$825
Return
found 1 day ago
Select Swiss International Air Lines flight, departing Thu, 22 Jan from London to Baltimore, returning Mon, 26 Jan, priced at S$825 found 1 day ago
Virgin Atlantic
Thu, 29 Jan - Wed, 4 Feb
LHR
London
BWI
Baltimore
S$876 Return, found 3 days ago
S$876
Return
found 3 days ago
Select Virgin Atlantic flight, departing Thu, 29 Jan from London to Baltimore, returning Wed, 4 Feb, priced at S$876 found 3 days ago

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

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 using the search bar to enter your travel dates, origin airport and whether you want a return 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.

Return prices range from S$250 - S$1,378 and one-ways Chestertown start as low as S$115.

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: Delta, United, American Airlines, Swiss International Air Lines, Virgin Atlantic. 

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 in a bag or bring hand baggage, it's worth checking 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 in/hand baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programmes 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 on 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 optimal times. Airfare to Chestertown (BWI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to BWI in February and in February 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.

Find Your Flights to Chestertown BWI

Travel information

Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Destination city name
Baltimore
Return price
S$249

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.

Air Canada
Tue, 14 Apr - Tue, 21 Apr
SIN
Singapore
BWI
Baltimore
S$1,378 Return, found 9 hours ago
S$1,378
Return
found 9 hours ago
Select Air Canada flight, departing Tue, 14 Apr from Singapore to Baltimore, returning Tue, 21 Apr, priced at S$1,378 found 9 hours ago

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