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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.

Frontier Airlines
Sat, Sep 12 - Sat, Oct 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 3, priced at $58 found 2 days ago
Frontier Airlines
Wed, Aug 19 - Sat, Aug 22
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 22, priced at $68 found 2 days ago
Frontier Airlines
Thu, Aug 20 - Sat, Aug 22
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$73 Roundtrip, found 2 days ago
$73
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 22, priced at $73 found 2 days ago
Frontier Airlines
Thu, Sep 3 - Sat, Sep 5
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 4 days ago
$80
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 3 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 5, priced at $80 found 4 days ago
Frontier Airlines
Mon, Aug 24 - Thu, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$81 Roundtrip, found 4 days ago
$81
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Sep 3, priced at $81 found 4 days ago
Frontier Airlines
Mon, Aug 24 - Thu, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Aug 24 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Sep 3, priced at $91 found 2 days ago
Frontier Airlines
Thu, Aug 6 - Wed, Aug 12
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$93 Roundtrip, found 5 days ago
$93
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 12, priced at $93 found 5 days ago
Frontier Airlines
Tue, Aug 18 - Tue, Aug 25
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$138 Roundtrip, found 15 hours ago
$138
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $138 found 15 hours ago
Delta
Sat, Nov 7 - Sat, Nov 7
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 7 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 7, priced at $152 found 2 days ago
American Airlines
Wed, Nov 4 - Tue, Nov 17
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Nov 4 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 17, priced at $251 found 1 hour ago
United
Wed, Sep 2 - Sat, Sep 12
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$263 Roundtrip, found 6 days ago
$263
Roundtrip
found 6 days ago
Select United flight, departing Wed, Sep 2 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 12, priced at $263 found 6 days ago
Bargain Flight
Tue, Sep 1 - Tue, Sep 15
AUS
Austin-Bergstrom Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$269 Roundtrip, found 4 days ago
$269
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, Sep 1 from Austin-Bergstrom Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 15, priced at $269 found 4 days ago
Delta
Wed, Nov 4 - Tue, Nov 17
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$271 Roundtrip, found 1 hour ago
$271
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Nov 4 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 17, priced at $271 found 1 hour ago
JetBlue Airways
Tue, Aug 11 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $325 found 1 day ago
Alaska Airlines
Tue, Sep 1 - Tue, Sep 15
AUS
Austin-Bergstrom Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$437 Roundtrip, found 4 days ago
$437
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Austin-Bergstrom Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 15, priced at $437 found 4 days ago
American Airlines
Wed, Aug 5 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$590 Roundtrip, found 4 days ago
$590
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Aug 5 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Aug 25, priced at $590 found 4 days 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 September, 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 $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
$57

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 ...
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Comfort Inn & Suites 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! (466 reviews)
"They could serve the breakfast and charge a little more, have a functional gym, have clean carpet in the room or hallway. Some are old!"

Reviewed on Jul 22, 2026

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

The Lodge at Great Oak Landing

3 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 ...
7.8/10 Good! (93 reviews)
"The room seemed very old, but OK generally. It looked out on a very unattractive storage area. Staff leaves at 4:30 and I got there a little later so the woman had to go back inside and get my information (which she said was already on my room door though I didn't see that). This is an old hotel ..."

Reviewed on Jul 20, 2026

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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 ...
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Historic Inns of Annapolis
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 ...
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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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 ...
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Pendry Baltimore
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 ...
8.2/10 Very Good! (1,000 reviews)
"Clean room but not everyday?"

Reviewed on Jul 21, 2026

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Hampton Inn Baltimore/Glen Burnie
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! (948 reviews)
"It was an amazing stay for us and definitely will be back."

Reviewed on Jul 22, 2026

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Annapolis Waterfront Hotel, Autograph Collection
See all 1,086 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.