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Chestertown

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Chestertown Flights as Low as $56

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

Frontier Airlines
Mon, Mar 23 - Mon, Apr 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 11 hours ago
$56
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Mon, Mar 23 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Apr 6, priced at $56 found 11 hours ago
Frontier Airlines
Tue, Feb 24 - Wed, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 5 hours ago
$66
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Feb 24 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 25, priced at $66 found 5 hours ago
Frontier Airlines
Thu, Feb 26 - Fri, Feb 27
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$67 Roundtrip, found 8 hours ago
$67
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Feb 27, priced at $67 found 8 hours ago
Spirit Airlines
Wed, Feb 11 - Wed, Feb 18
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Feb 11 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 18, priced at $68 found 2 days ago
Frontier Airlines
Sat, Feb 21 - Tue, Feb 24
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 5 hours ago
$68
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Feb 24, priced at $68 found 5 hours ago
Frontier Airlines
Thu, Feb 19 - Sat, Feb 21
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 5 hours ago
$70
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Feb 21, priced at $70 found 5 hours ago
Frontier Airlines
Fri, Feb 13 - Wed, Feb 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$73 Roundtrip, found 12 hours ago
$73
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Fri, Feb 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 18, priced at $73 found 12 hours ago
Frontier Airlines
Fri, Feb 27 - Mon, Mar 2
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Mar 2, priced at $82 found 1 day ago
Frontier Airlines
Tue, Feb 17 - Wed, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$82 Roundtrip, found 16 hours ago
$82
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Feb 17 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 25, priced at $82 found 16 hours ago
Frontier Airlines
Tue, Feb 17 - Mon, Feb 23
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$83 Roundtrip, found 16 hours ago
$83
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Feb 17 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Feb 23, priced at $83 found 16 hours ago
Delta
Mon, Mar 23 - Mon, Apr 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$157 Roundtrip, found 11 hours ago
$157
Roundtrip
found 11 hours ago
Select Delta flight, departing Mon, Mar 23 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Apr 6, priced at $157 found 11 hours ago
American Airlines
Thu, Feb 26 - Fri, Feb 27
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$187 Roundtrip, found 3 days ago
$187
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Feb 26 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Feb 27, priced at $187 found 3 days ago
United
Sat, Feb 14 - Wed, Feb 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$321 Roundtrip, found 3 days ago
$321
Roundtrip
found 3 days ago
Select United flight, departing Sat, Feb 14 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 18, priced at $321 found 3 days ago
American Airlines
Sat, May 2 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$450 Roundtrip, found 2 days ago
$450
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, May 2 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, May 5, priced at $450 found 2 days ago
American Airlines
Wed, Feb 4 - Sat, Feb 14
VPS
Northwest Florida Regional
SBY
Salisbury - Ocean City Wicomico Regional
$477 Roundtrip, found 4 days ago
$477
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Feb 4 from Northwest Florida Regional to Salisbury - Ocean City Wicomico Regional, returning Sat, Feb 14, priced at $477 found 4 days ago
American Airlines
Wed, May 20 - Tue, May 26
FLL
Fort Lauderdale - Hollywood Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$533 Roundtrip, found 1 day ago
$533
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 20 from Fort Lauderdale - Hollywood Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, May 26, priced at $533 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 March, 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 $56, 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 $56 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$56

Last Minute Hotel Deals in 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! (867 reviews)
Very nice

Reviewed on Dec 14, 2025

Get rates
Comfort Inn & Suites Chestertown
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 ...
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, and the staff was courteous and friendly.

Reviewed on Jan 5, 2026

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Pendry Baltimore
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! (1,898 reviews)
YES

Reviewed on Jan 20, 2026

Get rates
Historic Inns of Annapolis
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
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 ...
8/10 Very Good! (1,000 reviews)
Clean rooms

Reviewed on Jan 11, 2026

Get rates
Hampton Inn Baltimore/Glen Burnie
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Book a stay at this 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! (1,003 reviews)
The only bummer was the hot tub was out of commission.

Reviewed on Jan 14, 2026

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Hilton Garden Inn Baltimore/White Marsh
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! (1,138 reviews)
Staff too good. Felt at home for those 8 days I stayed there.. Coffee throughout and fresh

Reviewed on Jan 19, 2026

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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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
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! (1,034 reviews)
The room was clean. It was a good price for what I needed at the time and it was in a safe area with plenty of places to shop and eat.

Reviewed on Jan 13, 2026

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Quality Inn & Suites Bel Air I-95 Exit 77A
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (899 reviews)
Very welcoming and room very clean.

Reviewed on Jan 4, 2026

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Annapolis Waterfront Hotel, Autograph Collection
See all 1,090 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.