Title: Cheap Flights to Chestertown , NY - Expedia.ca ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Chestertown , NY - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d89045.Destination-Travel-Guides) ## Popular airlines to Chestertown - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![WestJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WS.svg) WestJet [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WS"}}]) - ![Flair Airlines](https://a.travel-assets.com/air/airlines/f8_sq.svg) Flair Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F8"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![Porter Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_PD.svg) Porter Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, New York, United States of America,departure:19/10/2025TANYT&leg2=from:Chestertown, New York, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"PD"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Frequently asked questions ### What is the name of Chestertown's airport? > Chestertown has just one airport, Albany Intl. Airport (ALB). ### How many airlines fly to Chestertown? > There are 7 airlines that jet into Chestertown from 23 airports across the globe. ### Which airlines fly to Chestertown? > United Airlines operates the majority of the flights to Chestertown. Catching a United Airlines flight from Washington is the most popular way of getting there. ### How many nonstop flights are there to Chestertown? > Flying to a new place is much more straightforward when there aren't any stopovers involved. If you're travelling to Chestertown, the awesome news is that there are approximately 290 direct flights operating each week. ### Where are the most popular flights to Chestertown departing from? > Travellers frequently jet off from Washington, Chicago and Baltimore airports when flying 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 see. From Washington to Chestertown, the average flight time is 1 hour and 28 minutes. From Chicago it's more like 1 hour and 58 minutes, and from Baltimore it's 1 hour and 17 minutes. ### How to book the cheapest flight to Chestertown? > Don't leave locking in your flight to Chestertown until the last possible moment. That's one move well-versed jet-setters use to get the best deals. Booking in advance means more choices and cheaper flights. Also, look around online and compare your options. If your destination has more than one airport, you may be able to pick up a great deal by flying into a less busy terminal. Lastly, another easy way to save some cash is be ready to book fast. If you stumble on a fantastic deal, don't think twice — grab it while you've got the chance. ### Do you have any tips for my flight to Chestertown? > Depending on where you're coming from, your flight to Chestertown could be simple and straightforward or it could go on forever. We've rounded up some useful tips that will help you start your next unforgettable escape on the right foot. What to pack in your hand luggage: > > > > - The secret to having a pain-free travel experience is to plan ahead. So, let's start with the essentials: passport, official ID, bank cards and important medications. Next, take on board items that'll help pass the time, like your laptop or a good read. It's also a wise idea to bring your chargers, a neck pillow and a pair of earplugs. Last but not least, don't forget to pop in toiletries like a toothbrush, lip balm and a clean T-shirt. > > > > Do not pack the following items in your hand luggage: > > > > - While the list of restricted items differs between airlines, the general rule to follow is avoid carrying anything sharp, flammable or explosive. This includes screwdrivers, drills, fireworks and fuel. Sporting equipment like ski poles, and objects that could harm other people, such as swords and batons, won't be allowed on board either. > > > > What to wear on a flight: > > > > - Comfort should be your main concern when choosing what to wear on your flight. Loose clothing is a sensible choice, as are enclosed shoes like sneakers. > - Deep vein thrombosis (DVT) is a risk on long-haul flights. It's the result of blood clots forming due to poor circulation, so do some gentle foot and leg exercises in your seat and consider wearing compression socks or tights. ### How to get through airport security fast when flying to Chestertown? > The trick is to be prepared before you reach the security gate. That way, you'll be stepping onto that plane to Chestertown in no time at all. Follow these helpful tips and get your vacation off to a flying start: > > > > - First things first. Your boarding pass and passport will need to be presented to airport security personnel. Keep them handy so you don't hold up the queue. > - Next up, both you and your carry-on luggage will be X-rayed. To speed things up, remove anything that is likely to set the alarm off. Personal belongings like your belt, jacket and earphones will be required to go through the machine. > - All your electronic devices, including your laptop and phone, will also need to be separately scanned. > - Remove gels and liquids from your hand luggage. They usually need to be sent through the X-ray machine separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit in a quart-size (one litre), clear zip-lock bag. > - There's a possibility that you'll be asked to take your shoes off to be X-rayed, so wearing lightweight sneakers is always a smart idea. > - Airlines will not allow any sharp objects to come on board with you. If you must bring these kinds of items, put them in your checked baggage. ## Book with confidence Expedia.ca gives you the best tools to secure great deals on flights to Chestertown. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Chestertown. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Chestertown. Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Chestertown flights with full confidence knowing that you've found the best deal online. Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Chestertown. Looking to save even more? Get additional savings by bundling your Chestertown flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Chestertown trip! ## Travel information | Destination airport | Chestertown | | --- | --- | | Destination airport IATA code | GFL | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [Farmstay in Adirondack](https://www.expedia.ca/Adirondack-Agritourism.d6349269-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adirondack](https://www.expedia.ca/Adirondack-Apart-Hotels.d6349269-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adirondack](https://www.expedia.ca/Adirondack-Bed-And-Breakfast.d6349269-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Adirondack](https://www.expedia.ca/Adirondack-Cabins.d6349269-aaCabins.Travel-Guide-Accommodation) - [Castles in Adirondack](https://www.expedia.ca/Adirondack-Castles.d6349269-aaCastles.Travel-Guide-Accommodation) - [Chalets in Adirondack](https://www.expedia.ca/Adirondack-Chalets.d6349269-aaChalets.Travel-Guide-Accommodation) - 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