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Chestertown

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Chestertown Flights as Low as $58

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

Spirit Airlines
Spirit Airlines
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Frontier Airlines
Frontier Airlines
Spirit Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Spirit Airlines
Delta
American Airlines
Delta
United
American Airlines

Cheap Flights to Chestertown

Fall in love at first flight with your vacation to Chestertown 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 Chestertown on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Chestertown

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chestertown 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 Chestertown?

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 Chestertown are in December, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chestertown?

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 Chestertown.

What airport is best to fly into Chestertown?

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

How much are flights to Chestertown?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chestertown on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $58, 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 Chestertown?

The trick to saving a stack of cash on your flight to Chestertown? 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 $58 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$58

Last Minute Hotel Deals in Chestertown

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $118 per night from Dec 15 to Dec 16
$118
includes taxes & fees
Dec 15 - Dec 16
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (727 reviews)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge."

Reviewed on Nov 15, 2024

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is $83 per night from Dec 1 to Dec 2
$83
includes taxes & fees
Dec 1 - Dec 2
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attraction ...
7.2/10 Good! (320 reviews)
Nice but no breakfast
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. ..."

Reviewed on Nov 10, 2024

Red Roof Inn & Suites Chestertown
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is $152 per night from Nov 24 to Nov 25
$152
includes taxes & fees
Nov 24 - Nov 25
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! (1,698 reviews)
"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."

Reviewed on Nov 21, 2024

Historic Inns of Annapolis
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center
2.5 out of 5
5625 O'Donnell Street, Baltimore, MD
The price is $115 per night from Dec 1 to Dec 2
$115
includes taxes & fees
Dec 1 - Dec 2
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,002 reviews)
"This location was in easy access to I95 and to all attractions in Baltimore. That being said, this close proximity was also a negative being in total view of I95. There was also a truck stop right across the front entrance of the hotel so it was noisy with all of the semi trucks around. Luckily, ..."

Reviewed on Nov 20, 2024

Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
The price is $90 per night from Nov 24 to Nov 25
$90
includes taxes & fees
Nov 24 - Nov 25
Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,001 reviews)
"Super attentive staff"

Reviewed on Nov 21, 2024

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Sagamore Pendry Baltimore
Sagamore Pendry Baltimore
5 out of 5
1715 Thames St., Baltimore, MD
The price is $417 per night from Dec 22 to Dec 23
$417
includes taxes & fees
Dec 22 - Dec 23
Stay at this 5-star luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (975 reviews)
"Property was beautiful. Terrance gave us a wonderful tour and history of the property. Wonderful stay."

Reviewed on Nov 19, 2024

Sagamore Pendry Baltimore
Hampton Inn Baltimore/Glen Burnie
Hampton Inn Baltimore/Glen Burnie
2.5 out of 5
6617 Ritchie Hwy, Glen Burnie, MD
The price is $117 per night from Nov 25 to Nov 26
$117
includes taxes & fees
Nov 25 - Nov 26
Book a stay at this business-friendly hotel in Glen Burnie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,001 reviews)
"Very nice breakfast"

Reviewed on Nov 5, 2024

Hampton Inn Baltimore/Glen Burnie
Quality Inn & Suites Bel Air I-95 Exit 77A
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
The price is $57 per night from Nov 24 to Nov 25
$57
includes taxes & fees
Nov 24 - Nov 25
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,001 reviews)
Skip the breakfast
"The breakfast was very basic, no meat, eggs juice or danish etc."

Reviewed on Nov 16, 2024

Quality Inn & Suites Bel Air I-95 Exit 77A
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.