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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
Wed, Sep 9 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 30, priced at $58 just found
Frontier Airlines
Wed, Jul 22 - Wed, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 6 hours ago
$60
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Jul 22 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jul 29, priced at $60 found 6 hours ago
Frontier Airlines
Thu, Aug 13 - Sat, Aug 15
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$74 Roundtrip, found 2 hours ago
$74
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 15, priced at $74 found 2 hours ago
Frontier Airlines
Mon, Sep 28 - Tue, Oct 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$76 Roundtrip, found 3 days ago
$76
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 13, priced at $76 found 3 days ago
Frontier Airlines
Sat, Jul 4 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$78 Roundtrip, found 4 days ago
$78
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jul 4, priced at $78 found 4 days ago
Frontier Airlines
Tue, Aug 25 - Sun, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$79 Roundtrip, found 3 days ago
$79
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 6, priced at $79 found 3 days ago
Frontier Airlines
Sat, Aug 22 - Sun, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$81 Roundtrip, found 3 days ago
$81
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 22 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 6, priced at $81 found 3 days ago
Frontier Airlines
Wed, Sep 9 - Thu, Oct 1
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 Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Oct 1, priced at $82 found 1 day ago
Frontier Airlines
Thu, Aug 13 - Tue, Aug 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Aug 13 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 18, priced at $84 found 3 days ago
Frontier Airlines
Wed, Aug 19 - Tue, Sep 1
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$142 Roundtrip, found 11 hours ago
$142
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Aug 19 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 1, priced at $142 found 11 hours ago
Delta
Wed, Sep 9 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Delta flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 30, priced at $237 just found
American Airlines
Wed, Sep 9 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$265 Roundtrip, just found
$265
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 30, priced at $265 just found
Bargain Flight
Sat, Jul 11 - Tue, Jul 14
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$281 Roundtrip, found 23 hours ago
$281
Roundtrip
found 23 hours ago
Select Bargain Flight flight, departing Sat, Jul 11 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 14, priced at $281 found 23 hours ago
Delta
Wed, Aug 19 - Tue, Sep 1
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$304 Roundtrip, found 11 hours ago
$304
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Aug 19 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 1, priced at $304 found 11 hours ago
JetBlue Airways
Wed, Sep 9 - Wed, Sep 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$365 Roundtrip, just found
$365
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Sep 9 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 30, priced at $365 just found
Alaska Airlines
Wed, Jul 1 - Sun, Jul 5
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$1,482 Roundtrip, found 1 day ago
$1,482
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Jul 1 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jul 5, priced at $1,482 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 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
$92

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 ...
8.6/10 Excellent! (926 reviews)
"Comfortable beds. Breakfast was decent, with hot and cold options. Shower did not have pressure. Pool was small but nice. Unfortunately we were there Wednesday -Sunday and never were given new towels or a room cleaning. And the last morning we found ants in the room."

Reviewed on Jun 14, 2026

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Comfort 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! (88 reviews)
"Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy."

Reviewed on Jun 16, 2026

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The Lodge at Great Oak Landing
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! (458 reviews)
"The property is a little older and could benefit from a good deep cleaning of carpets and upholstery, but the bed and bathroom were clean and the staff were great. Considering the price of other accomodations in the area it's an excellent value for the money if you're just looking for a clean place ..."

Reviewed on Jun 22, 2026

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Red Roof Inn & Suites Chestertown
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! (1,867 reviews)
"We were given a key to our room located at a site 2-3 blocks away. The room was lovely but the airconditioning was quite loud. We had no information given to us about facilities as the site was largely unstaffed other than cleaning and maintenance The location of the room itself was terrific."

Reviewed on Jun 27, 2026

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Historic Inns of Annapolis
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! (939 reviews)
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. ..."

Reviewed on Jun 17, 2026

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Annapolis Waterfront Hotel, Autograph Collection
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! (1,001 reviews)
"Loved the hotel ex"

Reviewed on Jun 25, 2026

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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 ...
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Best Western Plus Hotel & Conference Center
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! (1,004 reviews)
"Breakfast excellent. AC was aggressive. Was billed twice once from Expedia and at hotel though they did a credit at checkout. Tub had drip and toilet seat needs replacement"

Reviewed on Jun 26, 2026

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Hampton Inn Baltimore/Glen Burnie
See all 1,085 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.