Cheap Flights to Chestertown from $25

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Chestertown?

The cheapest prices found with in the last 7 days for return flights were $68 and $25 for one-way flights to Chestertown for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Sep 25 - Sun, Sep 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$73 Roundtrip, just found
$73
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 25 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 28, priced at $73 just found
OriginDestinationTravel DatesFlights From*
FLLBaltimoreOctober 7 to October 11$68
MCOBaltimoreOctober 23 to October 25$77
TPABaltimoreNovember 11 to November 16$83
DFWBaltimoreOctober 25 to October 25$91
LAXBaltimoreNovember 5 to November 11$99
MCOSalisburyOctober 31 to November 3$122
BOSBaltimoreOctober 21 to October 22$134
SJUSalisburyOctober 23 to October 27$235
ATLSalisburyNovember 14 to November 16$470
TPASalisburyOctober 11 to October 14$519
FLLSalisburyNovember 14 to November 19$525
DFWSalisburyNovember 22 to November 25$530
LAXSalisburyOctober 24 to October 31$637
PEKBaltimoreOctober 27 to November 2$1,177
PVGBaltimoreSeptember 30 to October 12$1,474
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ATLBaltimoreSeptember 19 to September 22$74
MCOBaltimoreSeptember 20 to September 21$83
FLLBaltimoreSeptember 19 to September 21$112
TPABaltimoreSeptember 19 to September 22$121
DFWBaltimoreSeptember 20 to September 24$171
BOSBaltimoreSeptember 21 to October 4$223
LAXBaltimoreSeptember 19 to September 21$239
SJUBaltimoreSeptember 20 to September 27$294
ATLSalisburySeptember 20 to September 27$558
SJUSalisburySeptember 20 to September 23$561
MCOSalisburySeptember 20 to September 24$583
DFWSalisburySeptember 21 to October 7$649
*Prices include taxes and fees

Chestertown Flight Information

Traveling to
Chestertown
Lowest Price
$68
Number of Airlines Serving
Airlines Serving
Spirit Airlines, Frontier Airlines
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Chestertown Accommodation Deals

Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
$64 nightly
The price is $70 total per night from Oct 14 to Oct 15
$70 total
Oct 14 - Oct 15
Total with taxes and fees
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Rolling Road Park and Historical Society of Kent ...
5/10 (174 reviews)
"Rooms are clean, staf was helpful"

Reviewed on Aug 18, 2025

Opens in a new windowDriftwood Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
$114 nightly
The price is $126 total per night from Sep 16 to Sep 17
$126 total
Sep 16 - Sep 17
Total with taxes and fees
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! (813 reviews)
"The room was spacious and very quiet."

Reviewed on Sep 6, 2025

Opens in a new windowComfort Inn & Suites 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.

Luxury Hotels in Chestertown

Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
$64 nightly
The price is $70 total per night from Oct 14 to Oct 15
$70 total
Oct 14 - Oct 15
Total with taxes and fees
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Rolling Road Park and Historical Society of Kent ...
5/10 (174 reviews)
"Rooms are clean, staf was helpful"

Reviewed on Aug 18, 2025

Opens in a new windowDriftwood Inn
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.

Family Friendly Hotels in Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
$114 nightly
The price is $126 total per night from Sep 16 to Sep 17
$126 total
Sep 16 - Sep 17
Total with taxes and fees
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! (813 reviews)
"The room was spacious and very quiet."

Reviewed on Sep 6, 2025

Opens in a new windowComfort Inn & Suites Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Great for families

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown
Book a stay at this family-friendly vacation home in Chestertown. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Rolling Road Park ...
9.8/10 Exceptional! (61 reviews)

Families like: Kitchen, close to beach, sofa bed, games and toys

Travelers say...
"The house and hospitality exceeded all expectations! We had a wonderful long weekend away and would definitely return. The kids especially loved fishing, kayaking, and the paddle boat. The farmer’s market was enjoyable Saturday morning, too. We had beautiful weather for yard games and the fire pit. ..."

Reviewed on Sep 1, 2025

Get rates
Opens in a new windowChester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
$64 nightly
The price is $70 total per night from Oct 14 to Oct 15
$70 total
Oct 14 - Oct 15
Total with taxes and fees
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Rolling Road Park and Historical Society of Kent ...
5/10 (174 reviews)
"Rooms are clean, staf was helpful"

Reviewed on Aug 18, 2025

Opens in a new windowDriftwood Inn
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.

Best Chestertown Flight and Hotel Packages

Chestertown flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Sahara Motel

Sahara Motel

2.5 out of 5
Price was $808, price is now $693 per person
$693
per person
Oct 17 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Salisbury (SBY)
Beach Walk

Beach Walk

2 out of 5
Price was $922, price is now $787 per person
$787
per person
Oct 17 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Salisbury (SBY)
Empress Motel

Empress Motel

2 out of 5
Price was $882, price is now $771 per person
$771
per person
Oct 17 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Columbus (CMH) to Salisbury (SBY)
Don't see what you're looking for?
See all available trips from Columbus to Chestertown
View all trips

Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Chestertown?
When it comes to booking your flight, it's always nice to have some choice. 18 airlines fly to the city of Chestertown, including:

  • Southwest Airlines
  • Delta Air Lines
  • Spirit Airlines

What airport is best to fly into Chestertown?
BWI Marshall is approximately 30 mi from central Chestertown. It's the sole airport servicing the city, so there's no possibility of your cab driver dropping you at the wrong one!
Where to stay in Chestertown
With 46 superb properties in Chestertown, you're spoilt for choice. But don't drag your feet. The sooner you book, the sooner you can start your adventure!Nothing beats the thrill of booking your accommodations for your next getaway. But after hours of comparing prices and amenities, it can get a little tiresome. So why not take our advice and choose one of our recommended properties, like the Country Estate in Historic District and the Carriage House Hideaway in Middle of Chestertown?
Places to visit in Chestertown
Learn about history and enjoy an exciting family outing with a visit to Historical Society of Kent County Maryland. Need some more options? Make sure to enjoy some of the artistic events regularly hosted by River Arts Chestertown and become more knowledgeable about the local arts and culture scene. And that's not all there is. Attend a play at Garfield Center for the Arts at the Prince Theater and relax as you see the plot thicken!
How to get through airport security fast when traveling to Chestertown
Make your journey to Chestertown a little bit easier by reading over these practical security tips:

  • Have your passport and boarding pass within easy reach. They'll be the first things you'll be asked for by security personnel.
  • Bear in mind that belts with metal buckles can set off the body scanner's alarms. If you have one on, you may be instructed to remove it before continuing.
  • Make sure your phone, laptop and other electronic devices are within easy reach. These items need to be put through the X-ray machine in separate trays.
  • Lip balm, toothpaste and other toiletry items in cream, liquid or gel form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock bag.
  • Security personnel will likely ask you to remove your shoes prior to entering the body scanner. Choose a pair that come off easily. There's nothing more tiresome than having to do up your laces again and again.
  • Some countries have strict quarantine laws. Think about where you're headed to and whether or not you're permitted to fly with fresh fruit and other foods.

Plane Tickets To Chestertown

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chestertown. Browse through our inventory to explore a wide range of cheap flights to Chestertown to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chestertown as you anxiously await to exit the plane and explore what Chestertown has to offer. Considering all the amazing local food and culture in Chestertown, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chestertown to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chestertown without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chestertown with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chestertown today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.