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 €113 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 €377 per night from 13 Jul to 14 Jul
€377
per night
13 Jul - 14 Jul
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 Maritime Museum. Free WiFi in public areas, 2 bars and a restaurant are available. This property offers pet-friendly amenities, such as food and water bowls.
9.4/10 Exceptional! (1,004 reviews)
"My favorite hotel."

Reviewed on 16 Jun 2026

Opens in a new windowPendry Baltimore
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is €118 per night from 12 Jul to 13 Jul
€118
per night
12 Jul - 13 Jul
Historic Inns of Annapolis's great location gets high marks from our customers. During your stay, you're just a quick walk from Annapolis City Dock. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a bar.
9/10 Wonderful! (1,887 reviews)
"We enjoyed ourselves the room was quaint. The shower rod in the bathroom was falling down, we asked them to fix it. They did but really the screw were stripped. It needs to be done properly. The nightstands with the built in plugs are terrible, they don’t charge. The one on the floor didn’t work. ..."

Reviewed on 15 Jun 2026

Opens in a new windowHistoric Inns of Annapolis
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 12 Jul to 13 Jul
€99
per night
12 Jul - 13 Jul
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.
8.6/10 Excellent! (924 reviews)
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."

Reviewed on 14 Jun 2026

Opens in a new windowComfort Inn & Suites Chestertown
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Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
The price is €96 per night from 5 Jul to 6 Jul
€96
per night
5 Jul - 6 Jul
The free breakfast at Hampton Inn Baltimore/Glen Burnie gets high marks from our customers. During your stay, you'll be close to Baltimore Cruise Terminal. You'll find features such as free WiFi in public areas and free self-parking, plus a 24-hour business centre.
8.2/10 Very Good! (1,017 reviews)
"My room was clean and spacious! Check in was very easy and the lady who checked me in was kind and helpful! The elevators are a little scary and need to be addressed. I had to leave before breakfast but it looked delicious! Check out was easy. I missed that there is no pool and that is totally on ..."

Reviewed on 15 Jun 2026

Opens in a new windowHampton Inn Baltimore/Glen Burnie
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
The price is €131 per night from 16 Jul to 17 Jul
€131
per night
16 Jul - 17 Jul
During your stay at The Lodge at Great Oak Landing, you'll be within walking distance of Chesapeake Bay. Free WiFi in public areas, free self-parking and a golf course are available.
7.8/10 Good! (87 reviews)
"We left 1 hour after arrival... Enough said! This is very much a buyer beware situation. It's no resort. There was absolutely no food available. Tiki bar is permanently closed. Small restaurant was also closed and our only option was food from the front desk. It's about a 30 minute drive to the closest ..."

Reviewed on 10 Jun 2026

Opens in a new windowThe Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
The price is €69 per night from 16 Jul to 17 Jul
€69
per night
16 Jul - 17 Jul
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! (457 reviews)
"Just ok"

Reviewed on 14 Jun 2026

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.