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Chestertown

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Chestertown Flights as Low as $75

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

Spirit Airlines
Tue, Aug 5 - Wed, Aug 6
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$75 Roundtrip, found 22 hours ago
$75
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 6, priced at $75 found 22 hours ago
Spirit Airlines
Tue, Jul 22 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 11 hours ago
$80
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jul 23, priced at $80 found 11 hours ago
Spirit Airlines
Sat, Aug 2 - Mon, Aug 4
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 22 hours ago
$87
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Aug 4, priced at $87 found 22 hours ago
Spirit Airlines
Tue, Aug 5 - Fri, Aug 8
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$89 Roundtrip, found 22 hours ago
$89
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Aug 8, priced at $89 found 22 hours ago
Spirit Airlines
Wed, Aug 6 - Sat, Aug 9
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$92 Roundtrip, found 6 hours ago
$92
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 9, priced at $92 found 6 hours ago
Spirit Airlines
Tue, Aug 5 - Tue, Aug 5
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$94 Roundtrip, found 22 hours ago
$94
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 5, priced at $94 found 22 hours ago
Frontier Airlines
Wed, Jul 16 - Sat, Jul 26
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$109 Roundtrip, found 21 hours ago
$109
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Jul 16 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jul 26, priced at $109 found 21 hours ago
Delta
Thu, Aug 7 - Thu, Aug 14
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$137 Roundtrip, found 22 hours ago
$137
Roundtrip
found 22 hours ago
Select Delta flight, departing Thu, Aug 7 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Aug 14, priced at $137 found 22 hours ago
American Airlines
Tue, Aug 5 - Thu, Aug 7
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$161 Roundtrip, found 2 hours ago
$161
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Aug 5 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Aug 7, priced at $161 found 2 hours ago
Spirit Airlines
Mon, Aug 25 - Thu, Aug 28
BDL
Bradley Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$175 Roundtrip, found 5 days ago
$175
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, Aug 25 from Bradley Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Aug 28, priced at $175 found 5 days ago
Delta
Sat, Oct 4 - Sat, Oct 4
DAL
Love Field
BWI
Baltimore Washington Intl. Thurgood Marshall
$231 Roundtrip, just found
$231
Roundtrip
just found
Select Delta flight, departing Sat, Oct 4 from Love Field to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 4, priced at $231 just found
United
Thu, Aug 28 - Mon, Sep 1
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select United flight, departing Thu, Aug 28 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 1, priced at $237 found 3 days ago
American Airlines
Wed, Aug 6 - Wed, Aug 13
ACY
Atlantic City Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$345 Roundtrip, found 2 hours ago
$345
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Aug 6 from Atlantic City Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Aug 13, priced at $345 found 2 hours ago
American Airlines
Wed, Aug 6 - Tue, Aug 12
BOS
Logan Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$357 Roundtrip, found 2 hours ago
$357
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Aug 6 from Logan Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Aug 12, priced at $357 found 2 hours ago
American Airlines
Wed, Jul 9 - Sat, Jul 12
BDL
Bradley Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 9 from Bradley Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Jul 12, priced at $408 found 1 day ago
American Airlines
Sat, Jul 19 - Tue, Jul 22
DFW
Dallas-Fort Worth Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$592 Roundtrip, found 4 hours ago
$592
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Jul 19 from Dallas-Fort Worth Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Jul 22, priced at $592 found 4 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 $75, 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 $75 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$75

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! (774 reviews)
"Room needed maintenance but nothing to interfere with sleeping. Bath/shower could use updating, appears uncleaned even though it was."

Reviewed on Jun 30, 2025

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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! (368 reviews)
"Great"

Reviewed on Jun 24, 2025

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Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 out of 5
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! (52 reviews)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"

Reviewed on Jun 22, 2025

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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 ...
8.8/10 Excellent! (1,789 reviews)
"Perfect for those that love American history"

Reviewed on Jun 29, 2025

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Historic Inns of Annapolis
Sagamore Pendry Baltimore
Sagamore Pendry Baltimore
5 out of 5
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! (1,006 reviews)
"The location was great, near shoppers and dining and with the breeze from the habor. The pool had next to no shade and ran out of lounges and even towels. We sat at the bar to get some shade and a seat when we got out of the pool. The concierge and desk staff knew very little about the area, attracts ..."

Reviewed on Jun 29, 2025

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Sagamore 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 ...
8/10 Very Good! (1,002 reviews)
"Courteous service. Clean room and comfortable bed. We enjoyed our stay. Would definitely stay again."

Reviewed on Jun 29, 2025

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Hampton Inn Baltimore/Glen Burnie
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
Stay at this 3-star business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
6.8/10 (1,012 reviews)
Would stay again
"Pros: easy check in, clean rooms, comfy king beds, super powerful showers Cons; room didn’t have bathtub, breakfast exactly the same for 3 day stay, one slow elevator."

Reviewed on Jun 29, 2025

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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
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! (830 reviews)
"The room was very nice. But the staff who serviced the room was not very good. Many days we did not have a shower mat, or extra toilet paper, or extra towels."

Reviewed on Jun 21, 2025

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Annapolis Waterfront Hotel, Autograph Collection
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.