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Chester

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Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BWI airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Easton - Newnam Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Chester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$449

Last Minute Hotel Deals in Chester

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,859 reviews)
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"

Reviewed on Sep 28, 2025

Historic Inns of Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Book a stay at this business-friendly hotel in Parole. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (899 reviews)
"Very clean."

Reviewed on Sep 27, 2025

Sonesta ES Suites Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,023 reviews)
"This was a convenient property for visiting the Naval Academy and historic Annapolis. The property seemed to be well taken care of. The breakfast was the usual breakfast area with a waffle maker, oatmeal, a hot serving dish of an egg product, a meat, and a potato product. Nothing fancy. The room ..."

Reviewed on Sep 22, 2025

Country Inn & Suites by Radisson, Annapolis, MD
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,020 reviews)
"everything was good except the hot tub at the pool was not available to use. other than that we were very pleased with everything"

Reviewed on Sep 29, 2025

Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,022 reviews)
"Staff was very friendly and professional"

Reviewed on Sep 29, 2025

DoubleTree by Hilton Hotel Annapolis
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,027 reviews)
"Restauranrs and good shopping within walking distance. 5 - 10 minutes However a 20 minute ride into the heart of Annapolis"

Reviewed on Sep 29, 2025

Best Western Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,001 reviews)
"When it takes two tries to get the room key to"

Reviewed on Sep 16, 2025

St Michaels Inn
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9/10 Wonderful! (1,000 reviews)
Good stay would stay again
"Stayed here to see my grandmother in a nursing home up the street. Nice stay for the night, nice hotel employees. Breakfast was soso the day we went. Everything else was fine. Pool area could’ve used a good cleaning."

Reviewed on Sep 8, 2025

SpringHill Suites by Marriott Annapolis
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.