Search Cheap Flights to
Chestertown

Name: Courtyard by Marriott Baltimore Downtown/McHenry Row
Rating: 9

Somewhere over the rainbow... Terrific view on the plane back to the North.

Photo by Assya A

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Chestertown Flights as Low as $151

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

All deals

One way

Roundtrip

Wed, Aug 13 - Tue, Aug 19

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$151

Roundtrip

found 5 days ago

Tue, Aug 19 - Wed, Aug 20

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$152

Roundtrip

found 5 days ago

Tue, Aug 12 - Tue, Aug 19

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$154

Roundtrip

found 5 days ago

Sat, Aug 16 - Tue, Aug 19

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$154

Roundtrip

found 5 days ago

Wed, Aug 13 - Wed, Aug 13

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$156

Roundtrip

found 5 days ago

Mon, Aug 25 - Thu, Sep 4

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$157

Roundtrip

found 4 days ago

Sat, Aug 23 - Thu, Sep 4

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$159

Roundtrip

found 4 days ago

Wed, Oct 22 - Wed, Oct 29

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$161

Roundtrip

found 3 days ago

Tue, Sep 30 - Tue, Oct 7

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$161

Roundtrip

found 1 day ago

Tue, Aug 19 - Sat, Aug 23

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$162

Roundtrip

found 5 days ago

Mon, Aug 25 - Fri, Sep 5

DEN

Denver Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$162

Roundtrip

found 4 hours ago

Mon, Aug 25 - Tue, Sep 2

BOS

Logan Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$183

Roundtrip

found 14 hours ago

Mon, Aug 25 - Fri, Sep 5

DEN

Denver Intl.

BWI

Baltimore Washington Intl. Thurgood Marshall

$217

Roundtrip

found 4 hours ago

Sat, Aug 9 - Wed, Aug 20

ACY

Atlantic City Intl.

SBY

Salisbury - Ocean City Wicomico Regional

$374

Roundtrip

found 4 days ago

Wed, Aug 6 - Sat, Aug 9

BOS

Logan Intl.

SBY

Salisbury - Ocean City Wicomico Regional

$404

Roundtrip

found 9 hours ago

Sat, Aug 2 - Tue, Aug 12

DEN

Denver Intl.

SBY

Salisbury - Ocean City Wicomico Regional

$607

Roundtrip

found 17 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 August, 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 $151, 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 $151 right now, why wait?

Chestertown Flight Information
Destination airport	Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code	BWI
Roundtrip price	$151

Last Minute Hotel Deals in Chestertown

Red Roof Inn & Suites Chestertown

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! (379 reviews)

SweetyPie The Explorer from Florida

"Our check-in quicl Staff was quick. The rooms have a very spacious area it was clean and the beds were comfortable just for a night to crash."

Reviewed on Jul 21, 2025

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Comfort Inn & Suites Chestertown

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! (785 reviews)

"Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall."

Reviewed on Jul 18, 2025

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The Lodge at Great Oak Landing

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! (55 reviews)

Getaway

"We love this place….awesome pool,and free golf….couldn’t ask for more 😃"

Reviewed on Jul 15, 2025

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Historic Inns of Annapolis

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! (1,812 reviews)

Awesome hotel!

"Loved this hotel. Extremely historic, clean, smells good and right across from the capital and close to the water and stores. My new place to stay when in this area."

Reviewed on Jul 24, 2025

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Sagamore Pendry Baltimore

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 ...

9.4/10 Exceptional! (1,007 reviews)

"BEST QUICK GET AWAY EVER !!!!! GREAT SERVICE, AND VERY FRIENDLY"

Reviewed on Jul 21, 2025

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Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St, Annapolis, MD

Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...

8.8/10 Excellent! (843 reviews)

Nice for a brief stay

"Great location and close to great restaurants. While pet friendly it was difficult to find a doggy potty area. The bathroom had had a leak that was barely patched and the bath had no fan. The parking was valet and we thought our car was parked in an enclosed area but we later saw it in a school parking ..."

Reviewed on Jul 24, 2025

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Quality Inn & Suites Bel Air I-95 Exit 77A

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! (1,008 reviews)

Budget friendly

"Solo dad on vacation, just looking for a good night's sleep on budget. Quality Inn came through for a very pleasant stay. Great A/C that was quiet, clean, spacious, actually had electrical outlets for my laptop and accessories. Nice water pressure for shower, adjacent parking, first floor so no stairs. ..."

Reviewed on Jul 15, 2025

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Courtyard by Marriott Baltimore Downtown/McHenry Row

1803 Porter Street, Baltimore, MD

Stay at this 3-star business-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

9/10 Wonderful! (634 reviews)

Great

"It was great but I left an item"

Reviewed on Jul 21, 2025

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See all 1,079 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.

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