Cheap flights from Chestertown

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Cheap round-trip flights from Chestertown

The lowest prices found within the past 7 days from Chestertown to were €173 for one-way flights and €327 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chestertown Flight Information
Origin airport IATA code
BWI

Sourcing the best flights from Chestertown on ebookers

If you’re seeking a flight from Chestertown, you can swiftly and easily find exactly what you’re looking for using ebookers. Our easy-to-use tool will let you select the destination and ideal travel dates to immediately see which routes and airlines are available. Have a preferred airline in mind for the trip? You can filter your ebookers search to see if they have flights from BWI. For more bespoke options, you can also set your search for multiple destinations and flights that are refundable, so you can have the most relevant information in moments.

Getting the best deal on a cheap flight from BWI

There are a few golden rules for keeping costs low when booking flights from Chestertown. The first thing to think about is being flexible on your travel dates. It can help to shift your departure by a day, or even a few hours, as prices can vary by significant amounts. Use ebookers to compare and contrast your options ahead of time, and you can make a savvy decision. Want more savings? If book the hotel at your chosen destination through ebookers while also arranging your flight from Chestertown, you can get a discount of up to 15% off the total price. For help on which pad to pick, you can make use of our snappy hotel descriptions, which are accompanied by useful photos.

Getting things going at your destination

With ebookers, you don’t just have access to the latest, constantly updated information on flights from BWI. You can also get inspiration on the most interesting things to get up to when you’re there. Just check out our Things to Do tool and you’ll soon be drawing up an exciting itinerary. And if you’re keen to take in as much of the wider area as possible, you could also look into the best car hire deals and have your very own set of wheels waiting, so you can roam to your heart’s content.

Featured Hotels near Chestertown

Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
The price is €368 per night from 7 Jan to 8 Jan
€368
7 Jan - 8 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Pendry Baltimore. During your stay, you're just a quick walk from Fell's Point Visitor Center. Free WiFi in public areas, 2 bars and a restaurant are available. This property offers pet-friendly amenities, such as food and water bowls.
9.2/10 Wonderful! (1,000 reviews)
Really nice cozy room we had the terrace balcony would definitely stay again!

Reviewed on 9 Dec 2025

Opens in a new windowPendry Baltimore
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
The price is €190 per night from 29 Dec to 30 Dec
€190
29 Dec - 30 Dec
includes taxes & fees
Annapolis Waterfront Hotel, Autograph Collection's great location gets high marks from our customers. During your stay, you're just a quick walk from U.S. Naval Academy. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
8.8/10 Excellent! (884 reviews)
Brittnay was very helpful during our check-in.

Reviewed on 13 Dec 2025

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Historic Inns of Annapolis's great location gets high marks from our customers. During your stay, you're just a quick walk from U.S. Naval Academy. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a bar.
8.8/10 Excellent! (1,904 reviews)
Great customer service!

Reviewed on 21 Dec 2025

Opens in a new windowHistoric Inns of Annapolis
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Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
The price is €99 per night from 11 Jan to 12 Jan
€99
11 Jan - 12 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Comfort Inn & Suites Chestertown. During your stay, you'll be within walking distance of Washington College. Enjoy features like free breakfast, free WiFi in public areas and free self-parking.
8.4/10 Very Good! (860 reviews)
Very nice

Reviewed on 14 Dec 2025

Opens in a new windowComfort Inn & Suites Chestertown
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
The price is €89 per night from 4 Jan to 5 Jan
€89
4 Jan - 5 Jan 2026
includes taxes & fees
The free breakfast at Best Western Plus Hotel & Conference Center gets good marks from our customers. During your stay, you'll be within walking distance of Johns Hopkins Bayview Medical Center. Free WiFi in public areas, free self-parking and an indoor pool are available.
7.8/10 Good! (1,000 reviews)
room is big and clean. Breakfast was good

Reviewed on 14 Dec 2025

Opens in a new windowBest Western Plus Hotel & Conference Center
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
The price is €68 per night from 28 Dec to 29 Dec
€68
28 Dec - 29 Dec
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Red Roof Inn & Suites Chestertown. During your stay, you'll be within walking distance of Washington College. You'll find features such as free WiFi in public areas and free self-parking, plus laundry facilities.
7.2/10 Good! (421 reviews)
Very clean. Pets allowed.

Reviewed on 14 Dec 2025

Opens in a new windowRed Roof Inn & Suites Chestertown
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.