Search Cheap Flights to
Chestertown

Photo by Assya A

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

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 , 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  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 , 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  right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$449

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
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! (396 reviews)
"Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service."

Reviewed on Sep 1, 2025

Red Roof Inn & Suites 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! (822 reviews)
"Well received by front desk attendant. Room clean!"

Reviewed on Sep 28, 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
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! (70 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"

Reviewed on Sep 5, 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
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! (1,859 reviews)
"So the entire experience was amazing. There was so much in walking distance. It was kind of weird because there were actually 3 inns and we didn't know which one we were in"

Reviewed on Sep 28, 2025

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 ...
9.2/10 Wonderful! (1,000 reviews)
"Absolutely great stay"

Reviewed on Sep 23, 2025

Sagamore Pendry Baltimore
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard, Baltimore, MD
Stay at this 3-star family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,027 reviews)
"I like"

Reviewed on Sep 29, 2025

Hilton Garden Inn Baltimore/White Marsh
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! (1,006 reviews)
"Clean and quiet"

Reviewed on Sep 20, 2025

Hampton Inn Baltimore/Glen Burnie
Quality Inn & Suites Bel Air I-95 Exit 77A

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

2.5 out of 5
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! (1,021 reviews)
I recommend!!
"Clean. Beautiful decor. Loved the hallway carpet. Bed could have been softer. Wallpaper needs to be removed and freshen with nice color of paint. Fantastic price for 2 adults!"

Reviewed on Sep 29, 2025

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