Cheap flights from Chester

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Chester Flight Information
Origin airport IATA code
BWI

Sourcing the best flights from Chester on ebookers

If you’re seeking a flight from Chester, 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 Chester. 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 Chester, 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 Chester

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD
During your stay at this holiday home, you'll be close to Island Dog Park. Free WiFi in public areas and laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
9.8/10 Exceptional! (94 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..

Reviewed on 14 Sept 2025

Opens in a new windowWaterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
The price is €141 per night from 15 Feb to 16 Feb
€141
15 Feb - 16 Feb
includes taxes & fees
Graduate by Hilton Annapolis's great location gets high marks from our customers. During your stay, you're just a quick walk from Asbury United Methodist Church. You'll find features such as 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.
9.2/10 Wonderful! (1,008 reviews)
Hotel is obviously not new. However it is very well maintained, very clean and we had a pleasant stay. Staff were professional and polite and allowed us an early checkin. Onsite restaurant was pretty good as well. Would stay again.

Reviewed on 21 Jan 2026

Opens in a new windowGraduate by Hilton Annapolis
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! (1,899 reviews)
YES

Reviewed on 20 Jan 2026

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

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
The price is €179 per night from 15 Feb to 16 Feb
€179
15 Feb - 16 Feb
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 Annapolis Harbor. 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! (900 reviews)
Very welcoming and room very clean.

Reviewed on 4 Jan 2026

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
The price is €72 per night from 8 Feb to 9 Feb
€72
8 Feb - 9 Feb
includes taxes & fees
Our customers tell us they can't get enough of DoubleTree by Hilton Hotel Annapolis's great location. During your stay, you'll be within walking distance of Annapolis Mall Shopping Center. You'll find features such as free WiFi in public areas, free self-parking and a free area shuttle.
8.6/10 Excellent! (1,006 reviews)
I only live an hour from this hotel, so I was prepared for a run home if I needed it, but no need. From the approach, the hotel was attractive. Parking was at a bit of a premium, but I got it sorted. I needed an accessible room, which was accessible by elevator (fine for my needs,) but not on the ...

Reviewed on 20 Jan 2026

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
The price is €144 per night from 28 Jan to 29 Jan
€144
28 Jan - 29 Jan
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at The Westin Annapolis. During your stay, you're just a quick walk from People's Brewer Hill Cemetery. You'll find features such as free WiFi in public areas, plus a full-service spa and an indoor pool.
8.6/10 Excellent! (1,003 reviews)
Clean room. Front desk was great and attentive. Ms. Shirley's restaurant is walking distance which is an amazing plus.

Reviewed on 22 Jan 2026

Opens in a new windowThe Westin Annapolis
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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.