Cheap Flights to Chestertown from $19
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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 $38 and $19 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* |
|---|---|---|---|
| ATL | Baltimore | November 18 to November 23 | $38 |
| FLL | Baltimore | November 17 to November 18 | $38 |
| DFW | Baltimore | December 9 to December 12 | $46 |
| FLL | Salisbury | November 14 to November 21 | $131 |
| DEN | Baltimore | December 12 to December 14 | $138 |
| MCO | Salisbury | December 4 to December 7 | $142 |
| BOS | Baltimore | November 10 to November 13 | $143 |
| LAX | Baltimore | November 14 to November 15 | $248 |
| SFO | Baltimore | January 22 to January 25 | $331 |
| BOS | Salisbury | November 11 to November 15 | $527 |
| CLT | Salisbury | November 21 to November 22 | $553 |
| ATL | Salisbury | January 21 to January 23 | $561 |
| FCO | Baltimore | November 26 to December 1 | $599 |
| SFO | Salisbury | December 29 to December 30 | $630 |
| DEN | Salisbury | January 14 to January 18 | $634 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Salisbury | October 30 to November 4 | $173 |
| FLL | Baltimore | October 30 to November 9 | $207 |
| MCO | Baltimore | October 30 to November 11 | $219 |
| ATL | Baltimore | October 31 to November 12 | $244 |
| CLT | Baltimore | November 1 to November 5 | $300 |
| DEN | Baltimore | October 31 to November 7 | $317 |
| BOS | Baltimore | November 1 to November 4 | $374 |
| LAX | Baltimore | October 31 to November 7 | $419 |
| DAL | Baltimore | October 31 to November 1 | $616 |
| SFO | Baltimore | October 31 to November 2 | $778 |
| FCO | Baltimore | November 1 to November 5 | $992 |
Chestertown Flight Information
Traveling to | Chestertown |
|---|---|
Lowest Price | $38 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Chestertown Accommodation Deals
Driftwood Inn
"Staff very friendly"
Reviewed on Sep 21, 2026
Comfort Inn & Suites Chestertown
Luxury Hotels in Chestertown
Driftwood Inn
"Staff very friendly"
Reviewed on Sep 21, 2026
Family Friendly Hotels in Chestertown
Comfort Inn & Suites Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Families like: Kitchen, close to beach, sofa bed, games and toys
"We very much enjoyed our stay. We were in town for a wedding. When we weren't involved in family activities, the house with the river front setting offered a tranquil retreat. I very much enjoyed just sitting in an Adirondack chair on the pier, while the younger folks got out on the paddle ..."
Reviewed on Oct 13, 2026
Driftwood Inn
"Staff very friendly"
Reviewed on Sep 21, 2026
Need a Car For After Your Flight?
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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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