Title: Cheap Flights to Chestertown , MD from CA $244 - Expedia.ca ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr ![](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Chestertown , MD from CA $244 [View CA $244 flight on Tue, Feb 3, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YVR,to:BWI,departure:03/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:243.15&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASjIloQDMJOXhAM4WEAAWAFqAlNWcghHSDRUQVZCTgotCMGmARIDMzc4GJIBIMFFKMOYhAMw8pqEAzhYQAFYAWoCU1ZyCE9IMk9YVUJOEgoIAhABGAIqAkFTGAEiBAgBEAEoAigDKAQwAQ) - [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.d7215.Travel-Guide-Hotels)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ## Popular airlines to Chestertown - ![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, Maryland, United States of America,departure:23/01/2026TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:30/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Breeze Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/30/landing_airline_sq_logo_MX.svg) Breeze Airways [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:23/01/2026TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:30/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}]) - ![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) ## How much is the cheapest flight to Chestertown? Prices were available within the past 7 days and start at CA $244 for one-way flights and CA $417 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Feb 24 - Wed, Feb 25 YYZ Toronto BWI Baltimore CA $422 Roundtrip found 14 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:BWI,departure:24/02/2026TANYT&leg2=from:BWI,to:YYZ,departure:25/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:421.82&airProductToken=AQpnCjIIwYIBEgQzNjA2GJjOASCuHCjihIYDMNqFhgM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAoxCMGCARIENDc4MRiuHCDBRSjWiIYDMNGJhgM4QkABWAFqBUJBU0lDcghPVkFIVlNCWApnCjEIwYIBEgQ0NTQwGMFFIK4cKIaNhgMwnI6GAzhCQABYAWoFQkFTSUNyCE9WQUhWU0JYCjIIwYIBEgQzNjEwGK4cIJjOASinkYYDMIyShgM4QkABWAFqBUJBU0lDcghPVkFDWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Feb 3 - Tue, Feb 10 YVR Vancouver BWI Baltimore CA $425 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:03/02/2026TANYT&leg2=from:BWI,to:YVR,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:424.06&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASjIloQDMJOXhAM4WEAAWAFqAlNWcghHSDRUQVZCTgotCMGmARIDMzc4GJIBIMFFKMOYhAMw8pqEAzhYQAFYAWoCU1ZyCE9IMk9YVUJOCmAKLQjBpgESAzM3ORjBRSCSASiO6oQDMPbshAM4WEAAWAFqAlNWcghPSDJPWFVCTgovCMGmARIEMzAwNRiSASC4jQEoqe2EAzDq7YQDOFhAAVgBagJTVnIIR0g0VEFWQk4SCggCEAEYAioCQVMYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 26 - Tue, Jan 27 YVR Vancouver BWI Baltimore CA $450 Roundtrip found 16 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:26/01/2026TANYT&leg2=from:BWI,to:YVR,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:449.78&airProductToken=AQqnAQo2CMSYARIEMzg4Nxi4jQEgkgEo-cKDAzDCw4MDOEVAAFgBaglNQUlOQkFTSUNyCFZBVVNBMEJRCjUIxJgBEgM4MTAYkgEg47QBKM7EgwMw0saDAzhFQAFYAWoJTUFJTkJBU0lDcghWQVVTQTBCQwo2CMSYARIEMTU0NhjjtAEgwUUo2ceDAzC_yIMDOEVAAVgBaglNQUlOQkFTSUNyCFZBVVNBMEJDCqQBCjQIxJgBEgM4NTcYwUUg4Fwo2smDAzDYyoMDOEVAAFgBaglNQUlOQkFTSUNyCFZBVVNBMEJDCjQIxJgBEgM0ODEY4FwgkgEoqcuDAzD0zYMDOEVAAVgBaglNQUlOQkFTSUNyCFZBVVNBMEJDCjYIxJgBEgQzODUzGJIBILiNASjfz4MDMJ_QgwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFVU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Feb 10 - Wed, Feb 18 YYC Calgary BWI Baltimore CA $581 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:BWI,departure:10/02/2026TANYT&leg2=from:BWI,to:YYC,departure:18/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:580.35&airProductToken=AQpvCjYI1YIBEgQxOTUzGJgWIINpKNnohAMw8emEAzhOQABYAWoKMV9iYXNpY2Vjb3IIR05BNEEyQk4KNQjVggESAzcwORiDaSDBRSiy6oQDMP_rhAM4TkAAWAFqCjFfYmFzaWNlY29yCEdOQTRBMkJOCm8KNgjVggESBDIwMTIYwUUgg2ko1cKFAzDRxIUDOE5AAFgBagoxX2Jhc2ljZWNvcghHTkE0QTJCTgo1CNWCARIDNzIwGINpIJgWKIjFhQMwpcaFAzhOQABYAWoKMV9iYXNpY2Vjb3IIR05BNEEyQk4SCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Tue, Mar 17 - Wed, Mar 25 YXX Abbotsford BWI Baltimore CA $843 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YXX,to:BWI,departure:17/03/2026TANYT&leg2=from:BWI,to:YXX,departure:25/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:842.71&airProductToken=AQqmAQoyCNemARIEMzY4Nhj4vQEgmBYoo_WHAzCC9ocDOEtAAFgBagVFQ09OT3IIS09VRDBaRVMKMQjXpgESBDE5OTIYmBYg4Fwo5vaHAzDt-IcDOEtAAVgBagVFQ09OT3IIS09VRDBaRVMKPQjXpgESBDcwMDAY4FwgwUUo8PmHAzDX-ocDOEtAAVgBagVFQ09OT3IIS09VRDBaRVN6CgjEmAESBDcwMDAKpQEKPQjXpgESBDcwNjYYwUUgzHwop8eIAzDSyIgDOExAAFgBagVFQ09OT3IITE9WRDBaRVN6CgjEmAESBDcwNjYKMQjXpgESBDE1MzEYzHwgmDEor8uIAzDjzIgDOExAAVgBagVFQ09OT3IITE9WRDBaRVMKMQjXpgESAzg0NRiYMSD4vQEojc6IAzDrzogDOExAAVgBagVFQ09OT3IITE9WRDBaRVMSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ## Frequently asked questions ### What is the name of Chestertown's airport? ### How far is BWI from central Chestertown? ### What airport is best to fly into Chestertown? ### How many airlines fly to Chestertown? ### Which airlines fly to Chestertown? ### How many nonstop flights are there to Chestertown? ### Where are the most popular flights to Chestertown departing from? ### How long is the flight to Chestertown Airport? ### How to book the cheapest flight to Chestertown? ### How to survive the flight to Chestertown? > - 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? > - 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. ## 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 | Baltimore Washington Intl. Thurgood Marshall | | ----------------------------- | -------------------------------------------- | | Destination airport IATA code | BWI | | Destination city name | Baltimore | | Roundtrip price | CA $408 | ## Trending flights to Chestertown Prices were available within the past 7 days and start at CA $244 for one-way flights and CA $417 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, Jan 31 - Sat, Jan 31 YVR Vancouver BWI Baltimore CA $417 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:31/01/2026TANYT&leg2=from:BWI,to:YVR,departure:31/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:416.36&airProductToken=AQpgCi8IwaYBEgQzMDA4GLiNASCSASjo9IMDMLP1gwM4WEAAWAFqAlNWcghHSDRUQVZCTgotCMGmARIDMzc4GJIBIMFFKOP2gwMwkvmDAzhYQAFYAWoCU1ZyCE9IMk9YVUJOCmAKLQjBpgESAzM3ORjBRSCSASjO-YMDMLb8gwM4WEAAWAFqAlNWcghPSDJPWFVCTgovCMGmARIEMzAwNRiSASC4jQEo6fyDAzCq_YMDOFhAAVgBagJTVnIIR0g0VEFWQk4SCggCEAEYAioCQVMYASIECAEQASgCKAMoBDAB) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [Apartments in Betterton ](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - 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