Cheap flights from Chestertown

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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 €379 per night from 17 Feb to 18 Feb
€379
17 Feb - 18 Feb
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! (1,002 reviews)
The hotel was beautiful, and the staff was courteous and friendly.

Reviewed on 5 Jan 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
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.
9/10 Wonderful! (1,906 reviews)
We had a wonderful stay at this here. The staff were incredibly accommodating, the room was clean and well-maintained, and the location was perfect. We would stay again

Reviewed on 25 Jan 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 €97 per night from 14 Feb to 15 Feb
€97
14 Feb - 15 Feb
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! (870 reviews)
Polite and kind hotel manager

Reviewed on 25 Jan 2026

Opens in a new windowComfort Inn & Suites Chestertown
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La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3 out of 5
2112b Emmorton Park Rd Edgewood MD
The price is €65 per night from 30 Jan to 31 Jan
€65
30 Jan - 31 Jan
includes taxes & fees
The free breakfast at La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A gets good marks from our customers. During your stay, you'll be close to CopperPlex. You'll find features such as free WiFi in public areas and free self-parking, plus laundry facilities.
8.2/10 Very Good! (1,004 reviews)
I was highly satisfied with my recent stay. The room was immaculately clean, which always makes a big difference for me. The overall atmosphere of the hotel was wonderfully inviting and relaxing. I would highly recommend this establishment to anyone seeking a great experience.

Reviewed on 22 Jan 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
The price is €103 per night from 8 Feb to 9 Feb
€103
8 Feb - 9 Feb
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Hilton Garden Inn Baltimore/White Marsh. During your stay, you're just a quick walk from White Marsh Mall. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.
7.8/10 Good! (1,003 reviews)
The only bummer was the hot tub was out of commission.

Reviewed on 14 Jan 2026

Opens in a new windowHilton Garden Inn Baltimore/White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
The price is €63 per night from 8 Feb to 9 Feb
€63
8 Feb - 9 Feb
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh. During your stay, you'll be close to White Marsh Mall. You'll find features such as free WiFi in public areas and free self-parking, plus a gym.
7/10 Good! (1,143 reviews)
Clean room, easy check in

Reviewed on 24 Jan 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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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.