Cheap Flights to Chestertown from $29

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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 $135 and $29 for one-way flights to Chestertown for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, May 2 - Tue, May 7
CMH
John Glenn Columbus Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 2 from John Glenn Columbus Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 7, priced at $135 found 4 days ago
OriginDestinationTravel DatesFlights From*
CMHBaltimoreMay 23 to May 26$150
CMHSalisburyJune 16 to June 22$368
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CMHBaltimoreApril 27 to April 30$279
CMHSalisburyApril 26 to May 4$482
*Prices include taxes and fees

Chestertown BWI Flight Information

Traveling to
Chestertown BWI
Lowest Price
$135
Number of Airlines Serving
1
Airlines Serving
Frontier Airlines, Spirit Airlines
Number of Daily Flights
3
Airlines with Direct Flights
Southwest Airlines

Find The Perfect Hotel For After Your Flight

Amazing Chestertown Accommodation Deals

Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
The price is $64 per night from Apr 20 to Apr 21
$64
per night
Apr 20 - Apr 21
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby. Discover ...
5/10 (159 reviews)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but ..."

Reviewed on Apr 4, 2024

Driftwood Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $110 per night from Apr 30 to May 1
$110
per night
Apr 30 - May 1
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (663 reviews)
"Super nice and friendly front desk staff. The room was very clean and spacious (suite). I’ve had less than positive experiences at other Comfort Inns, but this one is the exception. I’d absolutely stay here again!"

Reviewed on Apr 9, 2024

Comfort Inn & Suites Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Chestertown

Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
The price is $64 per night from Apr 20 to Apr 21
$64
per night
Apr 20 - Apr 21
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby. Discover ...
5/10 (159 reviews)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but ..."

Reviewed on Apr 4, 2024

Driftwood Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chestertown

Comfort Inn & Suites Chestertown
Great for families

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $110 per night from Apr 30 to May 1
$110
per night
Apr 30 - May 1
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (663 reviews)

Families like: Extra beds/cribs, free breakfast for the whole family, laundry

Travelers say...
"Super nice and friendly front desk staff. The room was very clean and spacious (suite). I’ve had less than positive experiences at other Comfort Inns, but this one is the exception. I’d absolutely stay here again!"

Reviewed on Apr 9, 2024

Comfort Inn & Suites Chestertown
Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
The price is $64 per night from Apr 20 to Apr 21
$64
per night
Apr 20 - Apr 21
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby. Discover ...
5/10 (159 reviews)
"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but ..."

Reviewed on Apr 4, 2024

Driftwood Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

  • 4 people
  • Unlimited mileage
Salisbury, Maryland, USA

$50

per day
found 1 day ago
Economy undefined

Compact

  • 5 people
  • Unlimited mileage
Salisbury, Maryland, USA

$50

per day
found 1 day ago
Compact undefined

Midsize

  • 5 people
  • Unlimited mileage
Salisbury, Maryland, USA

$52

per day
found 1 day ago
Midsize undefined

Standard

  • 5 people
  • Unlimited mileage
Salisbury, Maryland, USA

$54

per day
found 1 day ago
Standard undefined

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.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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!

*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.