
Popular airlines to Chestertown
- American Airlines
American Airlines
- Breeze Airways
Breeze Airways
- Alaska Airlines
Alaska Airlines
- Plan, book, fly with confidence
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How much is the cheapest flight to Chestertown?
Prices were available within the past 7 days and start at $32 for one-way flights and $68 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.





Alternative airports near Chestertown
Prices were available within the past 7 days. Prices and availability are subject to change.
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
August 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 2025 starts from from $68, while one-way tickets start from from $32. 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
Spirit Airlines, Frontier Airlines, Breeze Airways, Delta, Southwest Airlines 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, 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
Destination airport | Baltimore Washington Intl. Thurgood Marshall |
Destination airport IATA code | BWI |
Destination city name | Baltimore |
Roundtrip price | $67 |
Get up to 100% off your flight to Chestertown when booking a Flight + Hotel
Trending flights to Chestertown
Prices were available within the past 7 days and start at $32 for one-way flights and $68 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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Lodging
- Hotels near Washington College
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Rolphs Wharf Marina
- Worton Hotels
- Motels in Worton
- Church Hill Hotels
- Motels in Church Hill
- Kennedyville Hotels
- 4 Star Hotels in Kennedyville
- Apartments in Kennedyville
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- Cabin Rentals in Still Pond
- Great Oak Landing Hotels
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- Crumpton Hotels
- B&B in Crumpton
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- Hotels near Crumpton Auction
- Edesville Hotels
- Tolchester Beach Hotels
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- Price Hotels
- Betterton Hotels
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Packages
- Washington College
- River Arts Chestertown
- Historical Society of Kent County Maryland
- Garfield Center for the Arts at the Prince Theater
- Wilmer Park
- Rolphs Wharf Marina
- Worton Vacations
- Visit Worton
- Visit Church Hill
- Cassinelli Winery and Vineyards
- Visit Kennedyville
- Visit Still Pond
- Visit Great Oak Landing
- Visit Crumpton
- Visit Betterton
- Visit Rock Hall
- Rock Hall Vacations
- The Mainstay
- Rock Hall Harbor
- Waterman’s Museum
Cars
- Car rentals near Worton
- Car rentals near Pomona
- Car rentals near Fairlee
- Car rentals near Georgetown
- Car rentals near Church Hill
- Car rentals near Great Oak Landing
- Car rentals near Crumpton
- Car rentals near Crumpton Auction
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- Avis Rental Cars in Rock Hall