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Chester

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Chester Flights as Low as $57

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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American Airlines
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Delta

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 September, 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 16 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 $57, 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 $57 right now, why wait?

Chester Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$57

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 ...
9/10 Wonderful! (1,877 reviews)
"I loved the building. It’s in a lovely spot a block from the bay so shops and restaurants are right out the front door. The building I stayed in was terrific. The only bummer, was my room was quite small, so I would advise not staying in room 1408. It was the smallest room I’ve ever stayed in. I ..."

Reviewed on Jun 29, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,020 reviews)
"The room is as very musty smelling. The beds were way too soft. The ice makers didn’t work (one worked on one floor). When I asked to stay an extra night their price was even higher than expedias price. Just not impressed."

Reviewed on Jun 30, 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,008 reviews)
"It wasn’t the property or the room.. It was the unfriendly staff members. Not a single smile from the second we walked in… the front desk act as if we were bothering them.. never again"

Reviewed on Jun 29, 2026

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

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road 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 ...
9/10 Wonderful! (1,036 reviews)
"This hotel was fine for our one-night stopover in Annapolis. Location was good with plenty of free parking. The room was spacious, although fairly basic. Beds were clean and comfortable. On the down side, the foyer of the hotel wasn't very clean when we visited. Perhaps someone had just been in with ..."

Reviewed on Jun 24, 2026

Country Inn & Suites by Radisson, Annapolis, MD
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,003 reviews)
"Convenient location. Beautiful property. Friendly staff!"

Reviewed on Jun 27, 2026

Graduate by Hilton 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 ...
8.2/10 Very Good! (1,000 reviews)
"Short weekend trip, everything was good."

Reviewed on Jun 29, 2026

St Michaels Inn
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,005 reviews)
"Clean room. Great location"

Reviewed on Jun 30, 2026

Hilton Garden Inn Annapolis Downtown
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
Book a stay at this spa hotel in Annapolis. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,000 reviews)
"Ed frames broken, heavenly bed experience was compromised. This was the worst Westin hotel I have ever experienced"

Reviewed on Jun 16, 2026

The Westin 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.