Title: Cheap Flights to Chestertown , MD from CA $248 - 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 $248 [View CA $248 flight on Sat, Jan 17, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YYZ,to:BWI,departure:17/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:247.50&airProductToken=AQpnCjIIwYIBEgQzNjA2GJjOASCuHCim2YIDMJ7aggM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAoxCMGCARIEMzg1NBiuHCDBRSiv3YIDMKTeggM4QkABWAFqBUJBU0lDcghPN0FXWlNCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) - [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:21/10/2025TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:28/10/2025TANYT&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:21/10/2025TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}]) - ![Qatar Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_QR.svg) Qatar Airways [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:21/10/2025TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QR"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:21/10/2025TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:28/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) ![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 $248 for one-way flights and CA $468 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Wed, Dec 10 YVR Vancouver BWI Baltimore CA $468 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:09/12/2025TANYT&leg2=from:BWI,to:YVR,departure:10/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:467.74&airProductToken=AQqlAQo2CMSYARIEMzc2NBi4jQEgkgEog6X_AjDOpf8COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JDCjQIxJgBEgM5NDkYkgEgzHwo-6j_AjDHqv8COEVAAVgBaglNQUlOQkFTSUNyCFZBVk5BMEJRCjUIxJgBEgQyNTI2GMx8IMFFKLGr_wIw06z_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQqlAQo1CMSYARIEMjUyNhjBRSDMfCiHrf8CMK-u_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlEKNAjEmAESAzg3NxjMfCCSASiYr_8CMPyw_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlEKNgjEmAESBDM2OTgYkgEguI0BKKuy_wIw8LL_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Jan 7 - Sat, Jan 17 YYZ Toronto BWI Baltimore CA $485 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:BWI,departure:07/01/2026TANYT&leg2=from:BWI,to:YYZ,departure:17/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:484.15&airProductToken=AQqYAQoxCMGCARIENTY2OBiYzgEgQyjf54EDMM7ogQM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAowCMGCARIEMjE1MhhDIK4cKOjpgQMw-uqBAzhCQAFYAWoFQkFTSUNyCE9WQUNaU0JYCjEIwYIBEgQzODU0GK4cIMFFKO_sgQMw5O2BAzhCQAFYAWoFQkFTSUNyCE5WQUlWU0JYCmcKMQjBggESBDM4NDkYwUUgrhwo9NWCAzCL14IDOEJAAFgBagVCQVNJQ3IITzdBV1pTQloKMgjBggESBDM2MDgYrhwgmM4BKOjZggMwz9qCAzhCQAFYAWoFQkFTSUNyCE9WQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Mon, Oct 20 - Sat, Oct 25 YVR Vancouver BWI Baltimore CA $529 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:20/10/2025TANYT&leg2=from:BWI,to:YVR,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:528.75&airProductToken=AQqfAQo0CNWCARIEMjA4NRi4jQEgg2kowPH6AjDt8voCOEdAAFgBagdFQ09OT01ZcghHTkE0QTNURwoyCNWCARIDMzc3GINpIK4cKPTz-gIwi_X6AjhHQAFYAWoHRUNPTk9NWXIIR05BNEEzVEcKMwjVggESBDIzMDIYrhwgwUUosPj6AjCj-foCOEtAAVgBagdFQ09OT01ZcghLQUsyQVdEThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Tue, Nov 4 - Tue, Nov 18 YVR Vancouver BWI Baltimore CA $562 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:04/11/2025TANYT&leg2=from:BWI,to:YVR,departure:18/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:561.47&airProductToken=AQpECiEIwaYBEgQyMzA0GLiNASCSASjolvwCMK-X_AI4WEAAWAEKHwjBpgESAzM3OBiSASDBRSjjmPwCMJSb_AI4WEABWAEKRAofCMGmARIDMzQ5GMFFIJIBKNaz_QIwtrb9AjhYQABYAQohCMGmARIEMjMxMBiSASC4jQEo9rb9AjCzt_0COFhAAVgBEgoIARABGAEqAkFTGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Tue, Dec 23 - Mon, Dec 29 YVR Vancouver BWI Baltimore CA $673 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:23/12/2025TANYT&leg2=from:BWI,to:YVR,departure:29/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:672.01&airProductToken=AQpnCjII16YBEgQ2MzM0GLiNASDMfCidwYADMOzCgAM4S0AAWAFqBUVDT05PcghLT1VEMFpFUwoxCNemARIEODAzMRjMfCDBRSjVw4ADMPDEgAM4S0ABWAFqBUVDT05PcghLT1VEMFpFUwpnCjEI16YBEgQ3MDY2GMFFIMx8KJSAgQMwvoGBAzhLQABYAWoFRUNPTk9yCEtPVUQwWkVTCjII16YBEgQ2MzE1GMx8ILiNASidgoEDMJCEgQM4S0ABWAFqBUVDT05PcghLT1VEMFpFUxIKCAEQARgBKgJXUxgBIgQIARABKAIoAygEMAE) ## Alternative airports near Chestertown Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:BWI,departure:21/10/2025TANYT&leg2=from:BWI,to:CMH,departure:24/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) BWI Baltimore Washington Intl. Thurgood Marshall Cheapest 1 h 28 min [Flights from CA $570](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:BWI,departure:21/10/2025TANYT&leg2=from:BWI,to:CMH,departure:24/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) 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! Flights to Chestertown information | Destination airport | Baltimore Washington Intl. Thurgood Marshall | | --- | --- | | Destination airport IATA code | BWI | | Destination city name | Baltimore | | Roundtrip price | CA $468 | ## Need more than a Flight to Chestertown? Heading to Chestertown? Explore Chestertown with Expedia's Travel Guides to find the best hotels, vacation packages, car rental deals and more! [Chestertown Hotels](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide) ## Trending flights to Chestertown Prices were available within the past 7 days and start at CA $248 for one-way flights and CA $468 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Wed, Dec 10 YVR Vancouver BWI Baltimore CA $468 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YVR,to:BWI,departure:09/12/2025TANYT&leg2=from:BWI,to:YVR,departure:10/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:467.74&airProductToken=AQqlAQo2CMSYARIEMzc2NBi4jQEgkgEog6X_AjDOpf8COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNIM0JDCjQIxJgBEgM5NDkYkgEgzHwo-6j_AjDHqv8COEVAAVgBaglNQUlOQkFTSUNyCFZBVk5BMEJRCjUIxJgBEgQyNTI2GMx8IMFFKLGr_wIw06z_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCUQqlAQo1CMSYARIEMjUyNhjBRSDMfCiHrf8CMK-u_wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlEKNAjEmAESAzg3NxjMfCCSASiYr_8CMPyw_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTkEwQlEKNgjEmAESBDM2OTgYkgEguI0BKKuy_wIw8LL_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZTSDNCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ## Explore a world of travel with Expedia - 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[Worton Hotels](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels) ### Flights - [Flights to Aberdeen](https://www.expedia.ca/Cheap-Flights-To-Aberdeen.d6044.Travel-Guide-Flights) - [Flights to Annapolis](https://www.expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights) - [Flights to Arnold](https://www.expedia.ca/Cheap-Flights-To-Arnold.d74829.Travel-Guide-Flights) - [Flights to Baltimore Washington Intl. Thurgood Marshall](https://www.expedia.ca/Cheap-Flights-To-Baltimore-Washington-Intl-Thurgood-Marshall.d4806466.Travel-Guide-Flights) - [Flights to Baltimore](https://www.expedia.ca/Cheap-Flights-To-Baltimore.d178235.Travel-Guide-Flights) - [Flights to Bel Air](https://www.expedia.ca/Cheap-Flights-To-Bel-Air.d6023736.Travel-Guide-Flights) - [Flights to Chestnut Hill](https://www.expedia.ca/Cheap-Flights-To-Chestnut-Hill.d177622.Travel-Guide-Flights) - [Flights to Darlington](https://www.expedia.ca/Cheap-Flights-To-Darlington.d6123972.Travel-Guide-Flights) - [Flights to Dundalk](https://www.expedia.ca/Cheap-Flights-To-Dundalk.d98393.Travel-Guide-Flights) - [Flights to Eastern Shore](https://www.expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights) - [Flights to Edgewater](https://www.expedia.ca/Cheap-Flights-To-Edgewater.d6348965.Travel-Guide-Flights) - [Flights to Elkton](https://www.expedia.ca/Cheap-Flights-To-Elkton.d7834.Travel-Guide-Flights) - [Flights to Essex](https://www.expedia.ca/Cheap-Flights-To-Essex.d102297.Travel-Guide-Flights) - [Flights to Fallston](https://www.expedia.ca/Cheap-Flights-To-Fallston.d3000440569.Travel-Guide-Flights) - [Flights to Forest Hill](https://www.expedia.ca/Cheap-Flights-To-Forest-Hill.d6134319.Travel-Guide-Flights) - [Flights to Gibson Island](https://www.expedia.ca/Cheap-Flights-To-Gibson-Island.d3000347885.Travel-Guide-Flights) - [Flights to Halethorpe](https://www.expedia.ca/Cheap-Flights-To-Halethorpe.d111843.Travel-Guide-Flights) - [Flights to Kent Island](https://www.expedia.ca/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights) - [Flights to Linthicum Heights](https://www.expedia.ca/Cheap-Flights-To-Linthicum-Heights.d8629.Travel-Guide-Flights) - [Flights to Lutherville Timonium](https://www.expedia.ca/Cheap-Flights-To-Lutherville-Timonium.d128444.Travel-Guide-Flights) - [Flights to Middle River](https://www.expedia.ca/Cheap-Flights-To-Middle-River.d132920.Travel-Guide-Flights) - [Flights to North East](https://www.expedia.ca/Cheap-Flights-To-North-East.d139151.Travel-Guide-Flights) - [Flights to Northern Chesapeake Bay](https://www.expedia.ca/Cheap-Flights-To-Northern-Chesapeake-Bay.d6051456.Travel-Guide-Flights) - [Flights to Parkville](https://www.expedia.ca/Cheap-Flights-To-Parkville.d143755.Travel-Guide-Flights) - [Flights to Perryville](https://www.expedia.ca/Cheap-Flights-To-Perryville.d8217.Travel-Guide-Flights) - [Flights to St. Michaels](https://www.expedia.ca/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights) - [Flights to Towson](https://www.expedia.ca/Cheap-Flights-To-Towson.d7327.Travel-Guide-Flights) - [Flights to Western Shore of Maryland](https://www.expedia.ca/Cheap-Flights-To-Western-Shore-Of-Maryland.d6057468.Travel-Guide-Flights) - [Flights to Baltimore City County](https://www.expedia.ca/Destinations-In-Baltimore-City-County.d553248635997188102.Flight-Destinations) - [Flights to Maryland](https://www.expedia.ca/Destinations-In-Maryland.d222.Flight-Destinations) - [Flights from Gunpowder](https://www.expedia.ca/lp/flights/3000347895/flights-from-gunpowder) - [Flights from Kennedyville](https://www.expedia.ca/lp/flights/3000440679/flights-from-kennedyville) - [Flights from Massey](https://www.expedia.ca/lp/flights/3000440702/flights-from-massey) - [Flights from Barclay](https://www.expedia.ca/lp/flights/553248634998993874/flights-from-barclay) - [Flights from Centreville](https://www.expedia.ca/lp/flights/88125/flights-from-centreville) ### Packages - [Historical Society of Kent County Maryland](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Mount Harmon Plantation](https://www.expedia.ca/Mount-Harmon-Plantation-Earleville.d553248621561879694.Vacation-Attraction) - [Wilmer Park](https://www.expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) ### Cars - [Car rental Centreville](https://www.expedia.ca/Car-Rentals-In-Centreville.d88125.Car-Rental-Guide) ### Vacation Rental - [Centreville Vacation Rentals](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals) \*Available to Expedia members.