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Chestertown

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Chestertown Flights as Low as $46

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

Frontier Airlines
Wed, Dec 2 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$46 Roundtrip, found 1 hour ago
$46
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Dec 5, priced at $46 found 1 hour ago
Frontier Airlines
Wed, Nov 11 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 21 hours ago
$56
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 14, priced at $56 found 21 hours ago
Frontier Airlines
Wed, Nov 18 - Thu, Dec 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$63 Roundtrip, found 4 hours ago
$63
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Nov 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Dec 3, priced at $63 found 4 hours ago
Frontier Airlines
Wed, Dec 2 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$67 Roundtrip, found 1 hour ago
$67
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Dec 5, priced at $67 found 1 hour ago
Frontier Airlines
Tue, Nov 3 - Mon, Nov 16
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 12 hours ago
$68
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Nov 3 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 16, priced at $68 found 12 hours ago
Frontier Airlines
Fri, Dec 4 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$74 Roundtrip, found 1 hour ago
$74
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 14, priced at $74 found 1 hour ago
Frontier Airlines
Wed, Nov 11 - Wed, Dec 2
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Dec 2, priced at $76 found 1 day ago
Frontier Airlines
Mon, Nov 16 - Mon, Dec 7
ORD
O'Hare Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 16 from O'Hare Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 7, priced at $98 found 2 days ago
Frontier Airlines
Tue, Nov 3 - Sat, Nov 7
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Nov 3 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 7, priced at $139 found 2 days ago
Southwest Airlines
Sat, Nov 7 - Mon, Nov 16
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$203 Roundtrip, found 5 hours ago
$203
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Nov 7 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 16, priced at $203 found 5 hours ago
Delta
Fri, Dec 4 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$217 Roundtrip, found 1 hour ago
$217
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Dec 4 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Dec 14, priced at $217 found 1 hour ago
American Airlines
Wed, Nov 18 - Thu, Dec 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$273 Roundtrip, found 4 hours ago
$273
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Nov 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Dec 3, priced at $273 found 4 hours ago
Bargain Flight
Tue, Oct 27 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$295 Roundtrip, found 1 day ago
$295
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 28, priced at $295 found 1 day ago
JetBlue Airways
Wed, Nov 11 - Sat, Nov 14
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$339 Roundtrip, found 21 hours ago
$339
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Wed, Nov 11 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 14, priced at $339 found 21 hours ago
American Airlines
Fri, Oct 16 - Wed, Oct 21
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$632 Roundtrip, found 1 day ago
$632
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 16 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Oct 21, priced at $632 found 1 day ago
Alaska Airlines
Tue, Oct 27 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$748 Roundtrip, found 1 day ago
$748
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 28, priced at $748 found 1 day ago

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 15 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 $46, 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 $46 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$46

Last Minute Hotel Deals in Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
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 attractions ...
7.2/10 Good! (509 reviews)
"Hair dryer was broken and looked like it had been broken for awhile. Upon request staff provided one. Bed spread was clean but stained. No amenities at hotel not even list of restaurants close by. Hotel needs a complete renovation."

Reviewed on Oct 13, 2026

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Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
Get rates
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
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 ...
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Comfort Inn & Suites Chestertown
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
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! (1,226 reviews)
"Clean"

Reviewed on Oct 14, 2026

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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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! (2,050 reviews)
"It was a great experience."

Reviewed on Oct 14, 2026

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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
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 ...
8.2/10 Very Good! (1,001 reviews)
"Oh my goodness thanks to all who made our stay so covenant and comfortable. I would definitely suggest a stay here if you are in the area. Kindest Regards"

Reviewed on Oct 13, 2026

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Best Western Plus Hotel & Conference Center
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Book a stay at this 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! (1,000 reviews)
"Great service teams and beautiful property! Also had a large group family style dinner in the Rec Pier Chop House and the food and service was superb! I’d definitely stay here again!"

Reviewed on Oct 13, 2026

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Pendry Baltimore
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

2.5 out of 5
8225 Town Center Drive Baltimore MD
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
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Hampton Inn Baltimore/White Marsh
See all 1,100 properties in Chestertown
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.