Cheap Flights to Chestertown from $25

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How Much Does it Cost To Fly To Chestertown?

The cheapest prices found with in the last 7 days for return flights were $50 and $25 for one-way flights to Chestertown for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
MCOBaltimoreDecember 16 to January 1$55
ATLBaltimoreDecember 29 to January 7$58
DFWBaltimoreJanuary 12 to January 12$63
TPABaltimoreDecember 7 to December 8$64
SJUBaltimoreDecember 25 to December 31$87
MCOSalisburyJanuary 16 to January 19$122
LAXBaltimoreJanuary 26 to January 30$132
BOSBaltimoreJanuary 9 to January 13$150
ATLSalisburyNovember 22 to December 2$494
FLLSalisburyJanuary 23 to January 30$542
TPASalisburyJanuary 2 to January 9$547
DFWSalisburyDecember 5 to December 8$572
LAXSalisburyDecember 25 to January 3$642
PVGBaltimoreDecember 24 to January 28$1,102
PEKBaltimoreNovember 17 to November 25$1,172
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
FLLBaltimoreNovember 1 to November 2$125
MCOBaltimoreOctober 31 to November 2$130
MCOSalisburyOctober 31 to November 10$135
ATLBaltimoreNovember 1 to November 8$167
TPABaltimoreOctober 31 to November 2$208
DFWBaltimoreOctober 31 to November 3$232
BOSBaltimoreNovember 1 to November 2$242
LAXBaltimoreNovember 1 to November 4$283
SJUBaltimoreOctober 31 to November 10$307
PEKBaltimoreNovember 1 to November 14$1,944
*Prices include taxes and fees

Chestertown Flight Information

Traveling to
Chestertown
Lowest Price
$50
Number of Airlines Serving
Airlines Serving
Frontier Airlines
Number of Daily Flights
Airlines with Direct Flights

Need a Car For After Your Flight?

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!

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*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.