Search Cheap Flights to
Chestertown

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Chestertown Flights as Low as $60

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

Spirit Airlines
Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 7 hours ago
$60
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 19, priced at $60 found 7 hours ago
Spirit Airlines
Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$64 Roundtrip, found 7 hours ago
$64
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 19, priced at $64 found 7 hours ago
Frontier Airlines
Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$65 Roundtrip, found 7 hours ago
$65
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 19, priced at $65 found 7 hours ago
Frontier Airlines
Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 7 hours ago
$66
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Nov 19, priced at $66 found 7 hours ago
Frontier Airlines
Fri, Dec 12 - Sat, Dec 13
MIA
Miami Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Dec 12 from Miami Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Dec 13, priced at $68 found 1 day ago
Frontier Airlines
Tue, Jan 6 - Thu, Jan 8
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 18 hours ago
$68
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Jan 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jan 8, priced at $68 found 18 hours ago
Frontier Airlines
Wed, Nov 12 - Tue, Nov 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$69 Roundtrip, found 9 hours ago
$69
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Nov 12 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 18, priced at $69 found 9 hours ago
Frontier Airlines
Wed, Nov 12 - Thu, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Nov 12 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Nov 13, priced at $70 found 1 day ago
Frontier Airlines
Mon, Nov 10 - Mon, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$71 Roundtrip, found 9 hours ago
$71
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 17, priced at $71 found 9 hours ago
Delta
Tue, Jan 6 - Tue, Jan 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$154 Roundtrip, found 18 hours ago
$154
Roundtrip
found 18 hours ago
Select Delta flight, departing Tue, Jan 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jan 6, priced at $154 found 18 hours ago
American Airlines
Thu, Dec 4 - Sun, Dec 7
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$225 Roundtrip, found 3 days ago
$225
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 4 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Dec 7, priced at $225 found 3 days ago
United
Wed, Nov 19 - Sun, Nov 23
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$361 Roundtrip, found 3 days ago
$361
Roundtrip
found 3 days ago
Select United flight, departing Wed, Nov 19 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Nov 23, priced at $361 found 3 days ago
Delta
Wed, Nov 12 - Mon, Nov 17
VPS
Northwest Florida Regional
BWI
Baltimore Washington Intl. Thurgood Marshall
$372 Roundtrip, found 12 hours ago
$372
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Nov 12 from Northwest Florida Regional to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 17, priced at $372 found 12 hours ago
American Airlines
Tue, Feb 3 - Tue, Feb 17
VPS
Northwest Florida Regional
SBY
Salisbury - Ocean City Wicomico Regional
$401 Roundtrip, found 4 days ago
$401
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Feb 3 from Northwest Florida Regional to Salisbury - Ocean City Wicomico Regional, returning Tue, Feb 17, priced at $401 found 4 days ago
American Airlines
Tue, Feb 3 - Sat, Feb 7
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$430 Roundtrip, found 9 hours ago
$430
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Feb 3 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Feb 7, priced at $430 found 9 hours ago
American Airlines
Sat, Oct 25 - Sat, Nov 1
MIA
Miami Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$580 Roundtrip, found 3 hours ago
$580
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Oct 25 from Miami Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Nov 1, priced at $580 found 3 hours 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 November, 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 $60, 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 $60 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$60

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! (406 reviews)
Well received by front desk attendant. Clean room!

Reviewed on Oct 10, 2025

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Red Roof Inn & Suites Chestertown
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 ...
8.4/10 Very Good! (834 reviews)
Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly.

Reviewed on Oct 20, 2025

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Comfort 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
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (70 reviews)
Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!

Reviewed on Sep 5, 2025

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The Lodge at Great Oak Landing
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! (1,862 reviews)
Staff is always very friendly and efficient. Great location, valet is convenient. Only downsides were the bed mattress (big sag) and cold temperature in room. Heat might not have been turned on yet

Reviewed on Oct 18, 2025

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Historic Inns of Annapolis
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
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 ...
9.2/10 Wonderful! (1,007 reviews)
Such a beautiful hotel in a great location. No lack of bars or restaurants in Fells Point.

Reviewed on Oct 13, 2025

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Pendry Baltimore
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 ...
7.6/10 Good! (1,002 reviews)
We always stay here when in Baltimore.

Reviewed on Oct 16, 2025

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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

3 out of 5
4 Philadelphia Ct, Rosedale, MD
Stay at this 3-star 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! (1,026 reviews)
Clean nice

Reviewed on Oct 16, 2025

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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard, Baltimore, MD
Stay at this 3-star family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,021 reviews)
It was conveniently located. The room was spacious.

Reviewed on Oct 19, 2025

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Hilton Garden Inn Baltimore/White Marsh
See all 1,076 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.