Cheap Flights to Chestertown from $44
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How Much Does it Cost To Fly To Chestertown?
The cheapest prices found with in the last 7 days for return flights were $90 and $44 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 | October 5 to October 13 | $98 |
| BOS | Baltimore | October 21 to October 22 | $117 |
| MCO | Salisbury | October 5 to October 12 | $122 |
| FLL | Salisbury | August 19 to August 22 | $123 |
| DFW | Baltimore | August 26 to August 29 | $130 |
| LAX | Baltimore | August 29 to August 31 | $181 |
| SFO | Baltimore | September 1 to September 15 | $237 |
| DEN | Baltimore | September 29 to October 5 | $240 |
| BOS | Salisbury | September 1 to September 30 | $420 |
| CLT | Salisbury | October 16 to October 21 | $483 |
| ATL | Salisbury | October 24 to October 28 | $500 |
| DFW | Salisbury | October 7 to October 14 | $591 |
| DEN | Salisbury | August 28 to August 31 | $670 |
| LAX | Salisbury | September 9 to September 10 | $694 |
| FCO | Baltimore | October 14 to October 21 | $733 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | August 8 to August 8 | $145 |
| FLL | Salisbury | August 8 to August 22 | $175 |
| MCO | Salisbury | August 7 to August 14 | $186 |
| CLT | Baltimore | August 7 to August 9 | $201 |
| MCO | Baltimore | August 7 to August 11 | $246 |
| FLL | Baltimore | August 8 to August 12 | $248 |
| DFW | Baltimore | August 9 to August 26 | $264 |
| DEN | Baltimore | August 7 to August 9 | $360 |
| BOS | Baltimore | August 8 to August 16 | $434 |
| SFO | Baltimore | August 8 to September 11 | $435 |
| LAX | Baltimore | August 9 to August 18 | $460 |
| BOS | Salisbury | August 8 to August 15 | $504 |
| DEN | Salisbury | August 8 to August 12 | $717 |
| FCO | Baltimore | August 7 to August 14 | $1,297 |
Chestertown Flight Information
Traveling to | Chestertown |
|---|---|
Lowest Price | $90 |
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
Comfort Inn & Suites Chestertown
"We got a free upgrade just by asking!"
Reviewed on Jul 31, 2026
Luxury Hotels in Chestertown
Driftwood Inn
Family Friendly Hotels in Chestertown
Comfort Inn & Suites Chestertown
"We got a free upgrade just by asking!"
Reviewed on Jul 31, 2026
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Families like: Kitchen, close to beach, sofa bed, games and toys
"Great location and private setting on the river"
Reviewed on May 28, 2026
Driftwood Inn
Best Chestertown Flight and Hotel Packages
Chestertown flight + hotel packages - economy flights
Need a Car For After Your Flight?
Economy
Compact
Midsize
SUV
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!
Explore More Ways to Travel with Travelocity
- Houseboats in Chestertown
- Hotels in Chestertown
- The Lodge At Great Oak Landing
- Spa in Chestertown
- Red Roof Inn in Chestertown
- Pet Friendly in Chestertown
- Ocean View in Chestertown
- Luxury in Chestertown
- Indoor Pool in Chestertown
- Bar in Chestertown
- Pool in Chestertown
- Family Friendly in Chestertown
- Budget in Chestertown
- Hotels in Washington
- Hotels near Washington College
- Hotels near University Of Maryland Medical Center
- Hotels in Towson
- Hotels in St Michaels
- Hotels in Rock Hall
- Hotels in Pasadena
- Hotels near Oriole Park At Camden Yards
- Hotels near Northwest Stadium
- Hotels near National Aquarium In Baltimore
- Hotels near M&T Bank Stadium
- Hotels near Mgm National Harbor Casino
- Hotels near Maryland Live Casino
- 5 Star Hotels in Chestertown
- The Inn At Chesapeake Bay Beach Club
- Hotels in Annapolis
- Hotels near Arundel Mills Mall
- Hotels near Baltimore Convention Center
- Hot Tub in Baltimore
- Motel 6 Catonsville Md Baltimore West
- Hotels in Baltimore
- Houseboats in Baltimore
- Hotels in Kent Narrows
- Inner Harbor Hotels
- Guesthouses in Chestertown
- Aparthotels in Chestertown
- Cottages in Chestertown
- Cabins in Chestertown
- Bedandbreakfast in Chestertown
- Apartments in Chestertown
- Rod 'N' Reel Resort
- Hotels near Baltimore Md
- Hotels in Elkton
- Hotels in Easton
- Downtown Baltimore Hotels
- Maryland Hotels
- Romantic in Maryland
- Indoor Pool in Maryland
- Hot Tub in Maryland
- Beach in Maryland
- All-Inclusive in Maryland
- Motels in Chestertown
- Flights to Hanover
- Flights from Tampa (TPA) to Baltimore (BWI)
- Flights from Orlando (MCO) to Baltimore (BWI)
- Flights from Los Angeles (LAX) to Baltimore (BWI)
- Flights from Houston (IAH) to Baltimore (BWI)
- Flights from Dallas (DFW) to Baltimore (BWI)
- Flights from Boston (BOS) to Baltimore (BWI)
- Flights from Atlanta (ATL) to Baltimore (BWI)
- Flights from Baltimore Md
- Flights to Havre De Grace
- Flights to Joppa
- Flights to Linthicum Heights
- Flights to Middle River
- Flights to White Marsh
- Flights to Washington
- Flights to Towson
- Flights to Stevensville
- Flights to St Michaels
- Flights to Severn
- Flights to Rosedale
- Flights to Riva
- Flights to Parkville
- Flights to Odenton
- Flights to Aberdeen
- Flights to Annapolis
- Flights to Edgewood
- Flights to Elkton
- Flights to Essex
- Flights to Fort Meade
- Flights to Glen Burnie
- Flights to Baltimore
- Flights to Bel Air
- Flights to Conowingo
- Flights to Dundalk
- Flights to Eastern Shore
- Flights to Easton
- Flights to Edgewater
- Flights to Maryland