Search Cheap Flights to
Chestertown

Photo by Julie Miller

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 GFL 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 Floyd Bennett Memorial 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
Chestertown
Destination airport IATA code
GFL

Last Minute Hotel Deals in Chestertown

Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
2 out of 5
5537 State Route 8, Chestertown, NY
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ...
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"

Reviewed on Oct 28, 2024

Pine Tree Motel & Cabins
The Fern Lodge
The Fern Lodge
3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY
Stay at this 3.5-star beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ...
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."

Reviewed on Aug 27, 2024

The Fern Lodge
The Queensbury Hotel
The Queensbury Hotel
3 out of 5
88 Ridge St, Glens Falls, NY
Stay at this 3-star business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in ...
9.2/10 Wonderful! (1,257 reviews)
"This was a classic but modern 19th century hotel. The room was very spacious and we enjoyed walking the downtown area. Loved it!"

Reviewed on Jun 18, 2025

The Queensbury Hotel
Six Flags Great Escape Lodge & Indoor Waterpark
Six Flags Great Escape Lodge & Indoor Waterpark
3.5 out of 5
89 Six Flags Dr, Queensbury, NY
Stay at this 3.5-star family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,123 reviews)
"Great experience"

Reviewed on Jun 17, 2025

Six Flags Great Escape Lodge & Indoor Waterpark
Holiday Inn Resort Lake George - Adirondack Area by IHG
Holiday Inn Resort Lake George - Adirondack Area by IHG
3 out of 5
2223 Canada St, Lake George, NY
Stay at this 3-star family-friendly hotel in Lake George. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful ...
9.2/10 Wonderful! (1,001 reviews)
"We were at Americade and this was central and handy to multiple restaurants"

Reviewed on Jun 8, 2025

Holiday Inn Resort Lake George - Adirondack Area by IHG
Waterfront Home on Lake George w/ Boat Dock!
Waterfront Home on Lake George w/ Boat Dock!
3 out of 5
Queensbury
Stay at this 3-star cottage in Queensbury. Enjoy free parking, patios, and air conditioning. Popular attractions Million Dollar Beach and Lake George Steamboat ...
Waterfront Home on Lake George w/ Boat Dock!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3 out of 5
19 Skyline Drive, PO Box 269, Bolton Landing, NY
Stay at this 3-star golf castle in Bolton Landing. Enjoy free WiFi, free parking, and furnished balconies or patios. Popular attractions Veterans Memorial Park ...
"John and Yvonne were the perfect hosts hosts...Tvicolorfulsunse"

Reviewed on Aug 15, 2022

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
La Quinta Inn & Suites by Wyndham Lake George
La Quinta Inn & Suites by Wyndham Lake George
3 out of 5
1533 US-9, Lake George, NY
Stay at this 3-star family-friendly hotel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8.8/10 Excellent! (1,693 reviews)
"Staff was very friendly and helpful. The place was very well kept. The breakfast was excellent. Thoroughly enjoyed our stay."

Reviewed on Jun 16, 2025

La Quinta Inn & Suites by Wyndham Lake George
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.