Title: $28 Cheap Flights to Chestertown, MD - Expedia.com ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $28 Cheap Flights to Chestertown, MD [View $28 flight on Fri, May 15, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MCO,to:BWI,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:27.98&airProductToken=AQowCi4IxnISBDM2NjQYzHAgwUUo5IiNAzD4iY0DOEVAAFgBagRQQ18xcgdLMjFJWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers 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 [Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides) ## Popular airlines to Chestertown - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:2/28/2026TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/30/landing_airline_sq_logo_MX.svg) Breeze Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:2/28/2026TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"MX"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:2/28/2026TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_QR.svg) Qatar Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Chestertown, Maryland, United States of America,departure:2/28/2026TANYT&leg2=from:Chestertown, Maryland, United States of America,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QR"}}]) - ![](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\* - ![](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\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## How much is the cheapest flight to Chestertown? Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Fri, May 8 - Thu, May 14 MCO Orlando BWI Baltimore $56 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:BWI,departure:5/8/2026TANYT&leg2=from:BWI,to:MCO,departure:5/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDIzMTAYzHAgwUUo-buMAzCQvYwDOEVAAFgBagRQQ18xcgdLMjFEWFMyCjAKLgjGchIENDAwMxjBRSDMcCiYgY0DMLGCjQM4RUAAWAFqBFBDXzFyB0syMVJYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Fri, Mar 6 - Tue, Mar 10 ATL Atlanta BWI Baltimore $88 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:BWI,departure:3/6/2026TANYT&leg2=from:BWI,to:ATL,departure:3/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:87.86&airProductToken=AQpcCiwIzpYBEgQxNDkzGOBcIOVaKJz5hgMwjfqGAzhXQABYAWoCUlByBldBMTROUgosCM6WARIEMzIwMxjlWiDBRSi3_YYDMM7-hgM4V0ABWAFqAlJQcgZXQTE0TlISDAgBEAEYASoCTksyABgBIgQIARABKAIoAygEMA0) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Fri, May 15 - Mon, May 18 MCO Orlando SBY Salisbury $122 Roundtrip found 9 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:SBY,departure:5/15/2026TANYT&leg2=from:SBY,to:MCO,departure:5/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.22&airProductToken=AQotCisIzbABEgM4MjAYzHAgssABKJeKjQMwoYuNAzhBQABYAWoCTk9yBUFOTzAwCi0KKwjNsAESAzgyMRiywAEgzHAoqa2NAzC1ro0DOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Fri, Apr 24 - Sun, Apr 26 ATL Atlanta BWI Baltimore $167 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:BWI,departure:4/24/2026TANYT&leg2=from:BWI,to:ATL,departure:4/26/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:166.81&airProductToken=AQowCi4I15wBEgQzMzMxGOBcIMFFKM6diwMwwZ6LAzhEQABYAWoDV0dBcgdETE5XUjJFCjAKLgjXnAESBDE0NDUYwUUg4Fwo47SLAzDWtYsDOERAAFgBagNXR0FyB0RMTldSMkUSDAgBEAEYASoCV04yABgBIgQIARABKAIoAygEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Wed, May 13 - Tue, May 19 MCO Orlando BWI Baltimore $257 Roundtrip found 2 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:BWI,departure:5/13/2026TANYT&leg2=from:BWI,to:MCO,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:256.39&airProductToken=AQpvCjYI1YIBEgQyNDc1GMxwIK4cKMLxjAMw_PKMAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0FVMkFLQlMKNQjVggESAzQ1MBiuHCDBRSjE9IwDML71jAM4TkAAWAFqCjFfYmFzaWNlY29yCEtBVTJBS0JTCm8KNQjVggESAzM0ORjBRSCuHCiHso0DMJSzjQM4TkAAWAFqCjFfYmFzaWNlY29yCEtBVTJBS0JTCjYI1YIBEgQxNjQzGK4cIMxwKPKzjQMwpbWNAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0FVMkFLQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL) ## Alternative airports near Chestertown Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:BWI,departure:2/28/2026TANYT&leg2=from:BWI,to:CMH,departure:3/7/2026TANYT&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 $292 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:BWI,departure:2/28/2026TANYT&leg2=from:BWI,to:CMH,departure:3/7/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Tips to find the cheapest flights to Chestertown **The cheapest day to fly** Get started finding a cheap flight to Chestertown on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you. **The cheapest month to fly** May is the cheapest month to fly to Chestertown. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Chestertown. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. **The most affordable time to book a flight** Typically, a Sunday can be the cheapest time to book a flight to Chestertown, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. **The cheapest round-trip tickets to Chestertown** The lowest price for round-trip flights to Chestertown in 2026 starts from from $56, while one-way tickets start from from $28\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Chestertown. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Chestertown** Frontier Airlines, Spirit Airlines, Breeze Airways, American Airlines, Delta, Southwest Airlines, United are just some of the airlines that can typically offer cheap tickets to Chestertown. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Chestertown and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Chestertown, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Chestertown. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia. **Save with a package** With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Chestertown plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. **Date flexibility for the cheapest flights to Chestertown** If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Chestertown. **Stopover savings** The cheapest tickets to Chestertown are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Chestertown. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved. **Get Expedia's Price Drop Protection** Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Chestertown for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members. \*Terms apply. **Use our Price Tracking feature** Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Chestertown. Simply download the free Expedia app to your smart device and activate Chestertown flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices. **Book with Expedia** As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Chestertown. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. ## Frequently asked questions ### What month is the cheapest to fly to Chestertown? ### Which US cities have the cheapest flights to Chestertown? > - Ogdensburg (OGS) > - Lancaster (LNS) > - Plattsburgh (PBG) > - DuBois (DUJ) > - Morgantown (MGW) > > > with fares often starting from $30. ### Which US cities fly direct to Chestertown? > - Boston (BOS) > - Chicago (MDW, ORD) > - Atlanta (ATL) > - New York (JFK, LGA) > - Houston (HOU, IAH) > > > To Philadelphia Intl. (PHL) > - Orlando (MCO) > - Atlanta (ATL) > - Chicago (MDW, ORD) > - Charlotte (CLT) > - Fort Lauderdale (FLL) > > > To Baltimore Washington Intl. Thurgood Marshall (BWI) > - Atlanta (ATL) > - Orlando (MCO) > - Dallas (DAL, DFW) > - Houston (HOU, IAH) > - Chicago (MDW, ORD) ### How to find a cheap flight to Chestertown? ### Which airlines fly to Chestertown? > - American Airlines > - Delta > - Delta Air Lines > - Frontier Airlines > - JetBlue Airways > - Spirit Airlines > - United > - United Airlines ### Where do you fly into Chestertown? > - The closest major airport is Philadelphia, PA (PHL-Philadelphia Intl.), about 73 miles from the city center, which is a hub for American Airlines, Frontier Airlines, and Delta, with other airlines like United, Spirit Airlines also operating here. > - Washington, DC (DCA-Ronald Reagan Washington National) is another option, about 72 miles away, serving as a hub for American Airlines, United, and Delta, with JetBlue Airways, Air Canada also operating here. > - Washington, DC (IAD-Washington Dulles Intl.), about 97 miles away, serving as a hub for United, British Airways, and Delta, with TAP Portugal, Avianca also operating here. > - Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), about 42 miles away, serving as a hub for WN, Delta, and American Airlines, with Frontier Airlines, United also operating here. > - Harrisburg, PA (MDT-Harrisburg Intl.), about 83 miles away, serving as a hub for American Airlines, United, and Delta, with PT, Frontier Airlines also operating here. ### What is the cheapest airport to fly to in Chestertown? ### Which budget airlines fly to Chestertown? > - Frontier Airlines: serves Baltimore (BWI), Washington (DCA), Philadelphia (PHL), Washington (IAD), Harrisburg (MDT) > - Southwest Airlines: serves Baltimore (BWI), Washington (DCA), Philadelphia (PHL), Washington (IAD) > - Spirit Airlines: serves Baltimore (BWI), Philadelphia (PHL) > - JetBlue Airways: serves Washington (DCA), Philadelphia (PHL), Washington (IAD) > - Sun Country Airlines: serves Baltimore (BWI), Philadelphia (PHL), Washington (IAD) > - WestJet: serves Baltimore (BWI), Washington (DCA), Philadelphia (PHL), Washington (IAD), Harrisburg (MDT) > - Breeze: flies to Washington (IAD) > - GOL Linhas Aereas Inteligentes: serves Washington (DCA), Philadelphia (PHL) > - GOL Linhas Aereas S.A.: serves Washington (DCA), Philadelphia (PHL) > - Condor: serves Baltimore (BWI), Washington (DCA), Philadelphia (PHL) ### What is the best month to visit Chestertown? ### How far in advance should I book a flight to Chestertown? ### What day of the week is cheapest day to buy a plane ticket to Chestertown? ### What is the most expensive month to fly to Chestertown? ### How can I track flight prices to Chestertown? ### How to get a cheap last-minute flight to Chestertown? ### Can I earn miles booking a flight to Chestertown with Expedia? ### Can I save money by booking a Chestertown trip package? ### Can I change or cancel my flight to Chestertown? \*Flight schedules are subject to change. __Flights to Chestertown information__ | Destination airport | Baltimore Washington Intl. Thurgood Marshall | | ----------------------------- | -------------------------------------------- | | Destination airport IATA code | BWI | | Destination city name | Baltimore | | Roundtrip price | $56 | ## Trending flights to Chestertown Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Fri, May 8 - Thu, May 14 MCO Orlando BWI Baltimore $56 Roundtrip found 1 hour ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:BWI,departure:5/8/2026TANYT&leg2=from:BWI,to:MCO,departure:5/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDIzMTAYzHAgwUUo-buMAzCQvYwDOEVAAFgBagRQQ18xcgdLMjFEWFMyCjAKLgjGchIENDAwMxjBRSDMcCiYgY0DMLGCjQM4RUAAWAFqBFBDXzFyB0syMVJYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Washington College ](https://www.expedia.com/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels near River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) - 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