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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
Tue, Sep 15 - Wed, Sep 16
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 16, priced at $58 found 2 hours ago
Frontier Airlines
Tue, Aug 18 - Tue, Aug 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 1 hour ago
$60
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 18, priced at $60 found 1 hour ago
Frontier Airlines
Thu, Aug 13 - Sat, Aug 15
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$64 Roundtrip, found 3 days ago
$64
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 Sat, Aug 15, priced at $64 found 3 days ago
Frontier Airlines
Wed, Sep 9 - Wed, Sep 23
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$67 Roundtrip, found 1 day ago
$67
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 Wed, Sep 23, priced at $67 found 1 day ago
Frontier Airlines
Tue, Aug 11 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $68 found 1 day ago
Frontier Airlines
Tue, Aug 18 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 16 hours ago
$70
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $70 found 16 hours ago
Frontier Airlines
Tue, Sep 15 - Tue, Sep 29
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 29, priced at $128 found 1 day ago
American Airlines
Tue, Sep 1 - Tue, Sep 15
SEA
Seattle - Tacoma Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$227 Roundtrip, found 10 hours ago
$227
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Seattle - Tacoma Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 15, priced at $227 found 10 hours ago
Delta
Tue, Aug 18 - Tue, Aug 18
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 18, priced at $237 found 1 hour ago
Bargain Flight
Sun, Jul 26 - Tue, Jul 28
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$285 Roundtrip, found 17 hours ago
$285
Roundtrip
found 17 hours ago
Select Bargain Flight flight, departing Sun, Jul 26 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 28, priced at $285 found 17 hours ago
Delta
Tue, Aug 4 - Tue, Aug 18
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$297 Roundtrip, found 7 hours ago
$297
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Aug 4 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 18, priced at $297 found 7 hours ago
Alaska Airlines
Tue, Sep 1 - Tue, Sep 15
SEA
Seattle - Tacoma Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$377 Roundtrip, found 10 hours ago
$377
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Seattle - Tacoma Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 15, priced at $377 found 10 hours ago
JetBlue Airways
Sat, Sep 12 - Sat, Oct 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$385 Roundtrip, found 19 hours ago
$385
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Sat, Sep 12 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 3, priced at $385 found 19 hours ago
Alaska Airlines
Tue, Sep 1 - Tue, Sep 15
PAE
Seattle Paine Field Intl. Airport
BWI
Baltimore Washington Intl. Thurgood Marshall
$388 Roundtrip, found 10 hours ago
$388
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Tue, Sep 1 from Seattle Paine Field Intl. Airport to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 15, priced at $388 found 10 hours ago
American Airlines
Tue, Aug 11 - Sat, Aug 29
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$490 Roundtrip, found 7 hours ago
$490
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Aug 11 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Aug 29, priced at $490 found 7 hours ago
Sun Country Airlines
Wed, Aug 5 - Sun, Aug 9
SEA
Seattle - Tacoma Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$648 Roundtrip, found 5 days ago
$648
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Wed, Aug 5 from Seattle - Tacoma Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Aug 9, priced at $648 found 5 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
$98

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! (929 reviews)
"Problems with checking in and washing machine not working. Staff didn’t care."

Reviewed on Jun 29, 2026

Get rates
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! (89 reviews)
"Is a beautiful and quiet place to relax"

Reviewed on Jun 29, 2026

Get rates
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! (1,866 reviews)
"The staff was very friendly. The room was clean."

Reviewed on Jul 2, 2026

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Historic Inns of Annapolis
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 ...
8/10 Very Good! (1,002 reviews)
"Second time we've stayed at this hotel this year. Very nice rooms and very nice staff. The restaurant food and staff are also awesome."

Reviewed on Jun 28, 2026

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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! (1,000 reviews)
"Very poor not recommended"

Reviewed on Jun 29, 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 ...
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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.