Cheap Flight Deals to Chestertown MD from CA $308
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How to find cheap flights to Chestertown?
The cheapest prices found with in the last 7 days for return flights were CA $105 and CA $308 for one-way flights to Chestertown for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| FLL | Baltimore | May 9 to May 16 | CA $105 |
| MCO | Baltimore | May 6 to May 10 | CA $170 |
| TPA | Baltimore | May 15 to May 18 | CA $234 |
| ATL | Baltimore | May 22 to May 26 | CA $237 |
| BOS | Baltimore | June 26 to July 1 | CA $258 |
| LAX | Baltimore | May 28 to June 1 | CA $397 |
| DFW | Baltimore | May 18 to May 25 | CA $455 |
| SJU | Baltimore | June 5 to June 9 | CA $732 |
Your guide to flights to Chestertown, MD
Alaska Airlines, 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 $105 and CA $732. Prices vary, but for the best fares, travel in May 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 $105. 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 June 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
Dusty floor . Shower curtain didn’t close . Spiders on the ceiling
Reviewed on Nov 11, 2025
Comfort Inn & Suites Chestertown
The whole experience was great
Reviewed on Apr 23, 2026
Luxury Hotels in Chestertown
Driftwood Inn
Dusty floor . Shower curtain didn’t close . Spiders on the ceiling
Reviewed on Nov 11, 2025
Family Friendly Hotels in Chestertown
Comfort Inn & Suites Chestertown
The whole experience was great
Reviewed on Apr 23, 2026
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Friendly owners and neighbors on a very quiet private road with unbeatable river views and access. The fishing right off the dock is great.
Reviewed on Oct 27, 2025
Driftwood Inn
Dusty floor . Shower curtain didn’t close . Spiders on the ceiling
Reviewed on Nov 11, 2025
Need a car after flight to Chestertown?
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Frequently asked questions
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!
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