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Chestertown

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Chestertown Flights as Low as $410

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

American Airlines
Sun, May 25 - Sat, May 31
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$410 Roundtrip, found 12 hours ago
$410
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sun, May 25 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, May 31, priced at $410 found 12 hours ago
American Airlines
Sun, May 25 - Sat, May 31
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$471 Roundtrip, found 12 hours ago
$471
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sun, May 25 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, May 31, priced at $471 found 12 hours ago
American Airlines
Sun, May 25 - Sun, Jun 1
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$479 Roundtrip, found 12 hours ago
$479
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sun, May 25 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sun, Jun 1, priced at $479 found 12 hours ago
American Airlines
Tue, Jun 3 - Tue, Jun 10
MLB
Orlando Melbourne Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$481 Roundtrip, found 12 hours ago
$481
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Jun 3 from Orlando Melbourne Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Jun 10, priced at $481 found 12 hours ago
American Airlines
Sat, May 24 - Wed, May 28
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$486 Roundtrip, found 12 hours ago
$486
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sat, May 24 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, May 28, priced at $486 found 12 hours ago
American Airlines
Tue, May 27 - Sun, Jun 1
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$495 Roundtrip, found 12 hours ago
$495
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, May 27 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sun, Jun 1, priced at $495 found 12 hours ago
American Airlines
Wed, May 21 - Wed, May 28
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$502 Roundtrip, found 1 day ago
$502
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, May 21 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, May 28, priced at $502 found 1 day ago
American Airlines
Sun, May 25 - Sat, May 31
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$504 Roundtrip, found 12 hours ago
$504
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sun, May 25 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, May 31, priced at $504 found 12 hours ago
American Airlines
Thu, May 22 - Sat, May 31
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$509 Roundtrip, found 12 hours ago
$509
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, May 22 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, May 31, priced at $509 found 12 hours ago
American Airlines
Tue, May 6 - Sat, May 10
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$515 Roundtrip, found 3 days ago
$515
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, May 6 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, May 10, priced at $515 found 3 days ago
American Airlines
Fri, Jun 6 - Tue, Jun 10
MLB
Orlando Melbourne Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$516 Roundtrip, found 12 hours ago
$516
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Fri, Jun 6 from Orlando Melbourne Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Jun 10, priced at $516 found 12 hours ago
American Airlines
Thu, May 22 - Fri, May 30
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$517 Roundtrip, found 12 hours ago
$517
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, May 22 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Fri, May 30, priced at $517 found 12 hours ago
American Airlines
Mon, May 5 - Sat, May 10
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$520 Roundtrip, found 3 days ago
$520
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, May 5 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, May 10, priced at $520 found 3 days ago
American Airlines
Thu, May 22 - Wed, May 28
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$524 Roundtrip, found 12 hours ago
$524
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Thu, May 22 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, May 28, priced at $524 found 12 hours ago
American Airlines
Tue, May 6 - Sun, May 11
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$537 Roundtrip, found 3 days ago
$537
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, May 6 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Sun, May 11, priced at $537 found 3 days ago
American Airlines
Fri, May 23 - Fri, May 30
DAY
James M. Cox Dayton Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$539 Roundtrip, found 1 day ago
$539
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 23 from James M. Cox Dayton Intl. to Salisbury - Ocean City Wicomico Regional, returning Fri, May 30, priced at $539 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 May, 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 $410, 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 $410 right now, why wait?

Chestertown Flight Information
Destination airport
Salisbury - Ocean City Wicomico Regional
Destination airport IATA code
SBY
Roundtrip price
$409

Last Minute Hotel Deals in Chestertown

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is $76 per night from May 7 to May 8
$76
includes taxes & fees
May 7 - May 8
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! (345 reviews)
"Easy to get to, food all around!"

Reviewed on Apr 20, 2025

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $122 per night from May 7 to May 8
$122
includes taxes & fees
May 7 - May 8
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! (758 reviews)
"The room was nice and clean and the bathroom was recently updated. I was not able to connect my Roku to their WIFI however."

Reviewed on Apr 22, 2025

Comfort 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
The price is $163 per night from May 4 to May 5
$163
includes taxes & fees
May 4 - May 5
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 ...
7.6/10 Good! (48 reviews)
"Wonderful quiet place. Enjoyed our night."

Reviewed on Apr 27, 2025

The Lodge at Great Oak Landing
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is $199 per night from May 7 to May 8
$199
includes taxes & fees
May 7 - May 8
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! (1,757 reviews)
"We had an undesirable use of the shower. It was extremely small and without a reomoveable showerhead therefore making it impossible to bathe and rinse. At the least if there was a removeable wand/shower handle it would allow for a short person to have the spray hit more than just the top of their ..."

Reviewed on Apr 29, 2025

Historic Inns of Annapolis
Sagamore Pendry Baltimore
Sagamore Pendry Baltimore
5 out of 5
1715 Thames St., Baltimore, MD
The price is $427 per night from May 26 to May 27
$427
includes taxes & fees
May 26 - May 27
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! (1,001 reviews)
"Absolutely stunning property. Rooms are beautiful and CLEAN. The hotel itself is gorgeous and so well designed. This is our third stay and we will continue to treat ourselves to this wonderful luxurious hotel. The staff is extremely friendly and helpful. Can’t wait for our next stay!"

Reviewed on Apr 29, 2025

Sagamore 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
The price is $115 per night from May 11 to May 12
$115
includes taxes & fees
May 11 - May 12
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 ...
7.6/10 Good! (1,001 reviews)
"Very nice helpful staff"

Reviewed on Apr 21, 2025

Best Western Plus Hotel & Conference Center
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
The price is $159 per night from May 7 to May 8
$159
includes taxes & fees
May 7 - May 8
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9.4/10 Exceptional! (526 reviews)
"The staff is always amazing!!!!"

Reviewed on Apr 25, 2025

Hyatt Place Kent Narrows & Marina
Hampton Inn Baltimore Bayview Campus
Hampton Inn Baltimore Bayview Campus
3.5 out of 5
6571 Eastern Avenue, Baltimore, MD
The price is $142 per night from May 11 to May 12
$142
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,001 reviews)
"We had a wonderful stay at this hotel! The customer service was outstanding—everyone was so welcoming and helpful. The location is perfect, and the property itself is beautiful and well-maintained. My family and I truly enjoyed our time here and can’t wait to come back again soon!"

Reviewed on Apr 28, 2025

Hampton Inn Baltimore Bayview Campus
See all 1,075 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.