Cheap Flight Deals to Chestertown MD from CA $208

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

Change your flight without a fee on select flights

How to find cheap flights to Chestertown?

The cheapest prices found with in the last 7 days for return flights were CA $75 and CA $208 for one-way flights to Chestertown for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
BOSBaltimoreJanuary 7 to January 11CA $75
MCOBaltimoreJanuary 16 to January 19CA $110
ATLBaltimoreJanuary 14 to January 23CA $123
FLLBaltimoreJanuary 11 to January 12CA $141
TPABaltimoreJanuary 10 to January 19CA $169
LAXBaltimoreJanuary 23 to January 29CA $199
DFWBaltimoreJanuary 15 to January 26CA $240
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLBaltimoreDecember 27 to December 31CA $248
BOSBaltimoreDecember 28 to January 1CA $285
MCOBaltimoreDecember 29 to January 2CA $316
*Prices include taxes and fees

Your guide to flights to Chestertown, MD

Delta fly to Chestertown, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chestertown MD currently costs between CA $75 and CA $339. Prices vary, but for the best fares, travel in January when prices are at their lowest.  

Top tips for finding cheap flights to Chestertown  

The cheapest flight for a round trip to Chestertown is currently CA $75. When you search for flights to Chestertown, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chestertown for nearby days.  The cheapest month to travel to Chestertown is January from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Chestertown 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Chestertown with Travelocity 

We have top deals on plane tickets even for last minute flights to Chestertown, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chestertown for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Chestertown

Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
The price is CA $91 per night from Dec. 25 to Dec. 26
CA $91
per night
Dec. 25 - Dec. 26
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
5/10 (167 reviews)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

Reviewed on 16 Oct. 2024

Driftwood Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is CA $156 per night from Jan. 6 to Jan. 7
CA $156
per night
Jan. 6 - Jan. 7
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! (734 reviews)
Nice hotel
"Front desk staff was welcoming and friendly. We had a suite so I am guessing it was a bit larger than a regular room but it was really wonderful to have the extra space. The room was clean and the breakfast was decent (the coffee was good for hotel coffee). Would certainly stay here again when I ..."

Reviewed on 13 Dec. 2024

Comfort 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
The price is CA $91 per night from Dec. 25 to Dec. 26
CA $91
per night
Dec. 25 - Dec. 26
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
5/10 (167 reviews)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

Reviewed on 16 Oct. 2024

Driftwood 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
The price is CA $156 per night from Jan. 6 to Jan. 7
CA $156
per night
Jan. 6 - Jan. 7
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! (734 reviews)
Nice hotel
"Front desk staff was welcoming and friendly. We had a suite so I am guessing it was a bit larger than a regular room but it was really wonderful to have the extra space. The room was clean and the breakfast was decent (the coffee was good for hotel coffee). Would certainly stay here again when I ..."

Reviewed on 13 Dec. 2024

Comfort Inn & Suites Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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 patios. Popular attraction Rolphs Wharf Marina is located ...
9.8/10 Exceptional! (57 reviews)
Great location!
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."

Reviewed on 8 Nov. 2024

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

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
The price is CA $91 per night from Dec. 25 to Dec. 26
CA $91
per night
Dec. 25 - Dec. 26
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
5/10 (167 reviews)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

Reviewed on 16 Oct. 2024

Driftwood 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.
Red Roof Inn & Suites Chestertown
Ashore Resort & Beach Club
Grand Hotel Ocean City Oceanfront
Don't see what you're looking for?
See all available trips from Edmonton to Chestertown
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Need a car after flight to Chestertown?

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 48 kilometers 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
0 Like some more options? 0 But that’s not all. 0
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.