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 $49 and $25 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 | February 7 to February 15 | $53 |
| ATL | Baltimore | February 24 to February 25 | $56 |
| DFW | Baltimore | February 19 to February 23 | $69 |
| MCO | Salisbury | March 6 to March 9 | $122 |
| BOS | Baltimore | February 24 to February 25 | $130 |
| LAX | Baltimore | February 18 to February 25 | $164 |
| SFO | Baltimore | March 9 to March 17 | $217 |
| CLT | Salisbury | April 10 to April 12 | $439 |
| BOS | Salisbury | March 24 to April 1 | $440 |
| ATL | Salisbury | March 24 to April 1 | $450 |
| FLL | Salisbury | March 26 to March 30 | $560 |
| FCO | Baltimore | April 7 to April 14 | $561 |
| DFW | Salisbury | April 15 to April 19 | $565 |
| DEN | Salisbury | February 27 to March 2 | $598 |
| LAX | Salisbury | April 11 to April 17 | $649 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| MCO | Baltimore | January 31 to February 8 | $82 |
| FLL | Baltimore | January 31 to February 1 | $83 |
| CLT | Baltimore | February 1 to February 12 | $164 |
| MCO | Salisbury | January 30 to February 9 | $168 |
| DFW | Baltimore | January 31 to February 15 | $188 |
| ATL | Baltimore | January 31 to February 1 | $196 |
| BOS | Baltimore | January 31 to February 7 | $229 |
| LAX | Baltimore | January 30 to February 1 | $274 |
| DEN | Baltimore | January 31 to February 4 | $287 |
| SFO | Baltimore | January 31 to February 14 | $375 |
| FCO | Baltimore | February 1 to February 17 | $624 |
| FLL | Salisbury | January 30 to February 4 | $660 |
Chestertown Flight Information
Traveling to | Chestertown |
|---|---|
Lowest Price | $49 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Chestertown Accommodation Deals
Driftwood Inn
Rooms are clean, staf was helpful
Reviewed on Aug 18, 2025
Comfort Inn & Suites Chestertown
staff is nice and place is good. proce wise is excellent
Reviewed on Jan 23, 2026
Luxury Hotels in Chestertown
Driftwood Inn
Rooms are clean, staf was helpful
Reviewed on Aug 18, 2025
Family Friendly Hotels in Chestertown
Comfort Inn & Suites Chestertown
staff is nice and place is good. proce wise is excellent
Reviewed on Jan 23, 2026
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Families like: Kitchen, close to beach, sofa bed, games and toys
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
Rooms are clean, staf was helpful
Reviewed on Aug 18, 2025
Need a Car For After Your Flight?
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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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