Cheap flights To Chestertown (BWI) from $55

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Cheap Flights to Chestertown from $55 One Way, $97 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Nov 4 - Mon, Nov 9
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Nov 4 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 9, priced at $97 found 3 days ago
Wed, Nov 4 - Mon, Nov 9
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Nov 4 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Nov 9, priced at $107 found 3 days ago
Wed, Aug 26 - Wed, Aug 26
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$110 Roundtrip, found 11 hours ago
$110
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 26, priced at $110 found 11 hours ago
Wed, Sep 2 - Sat, Sep 5
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$112 Roundtrip, found 4 hours ago
$112
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 5, priced at $112 found 4 hours ago
Wed, Aug 26 - Tue, Sep 1
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$113 Roundtrip, found 5 days ago
$113
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 1, priced at $113 found 5 days ago
Tue, Sep 29 - Sat, Oct 3
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$115 Roundtrip, found 10 hours ago
$115
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Oct 3, priced at $115 found 10 hours ago
Thu, Sep 3 - Thu, Sep 10
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$119 Roundtrip, found 21 hours ago
$119
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Sep 3 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Sep 10, priced at $119 found 21 hours ago
Wed, Oct 7 - Tue, Oct 20
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Oct 7 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 20, priced at $119 found 1 day ago
Tue, Sep 22 - Wed, Sep 30
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$120 Roundtrip, found 5 days ago
$120
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 30, priced at $120 found 5 days ago
Wed, Oct 21 - Wed, Oct 28
FLL
Fort Lauderdale - Hollywood Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Oct 21 from Fort Lauderdale - Hollywood Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Oct 28, priced at $122 found 3 days ago

Chestertown Flight Information

Traveling To
Chestertown
Destination Airport IATA Code
BWI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, Delta, Breeze Airways
Flight Price
$97
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Chestertown economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sea Breeze Inn
2.0-star property

Sea Breeze Inn

Sep 17 - Sep 20

3 night stay

Atlanta (ATL) to Salisbury (SBY)

American Airlines • Non-stop roundtrip • Coach
Price was $1,339, price is now $936 per person
$936
per person
found 3 hours ago
Hampton Inn Salisbury
2.5-star property

Hampton Inn Salisbury

Sep 17 - Sep 20

3 night stay

Atlanta (ATL) to Salisbury (SBY)

American Airlines • Non-stop roundtrip • Coach
Price was $950, price is now $945 per person
$945
per person
found 3 hours ago
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Chestertown

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Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Chestertown flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Chestertown again.

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Low Prices for Chestertown Flights

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Frequently asked questions

Which airlines fly to Chestertown?
With 20 airlines operating services to Baltimore Washington Intl. Thurgood Marshall Airport (BWI), the gateway to Chestertown, you have loads of choice. Land an excellent deal among these top international carriers waiting to fly you away to this city:

  • Southwest Airlines - 48 flights to Chestertown per month
  • Air Canada - 35 flights to Chestertown per month
  • Spirit Airlines - 25 flights to Chestertown per month

What is the best airport to fly to in Chestertown?
Keep an eye out for a cheap ticket to Baltimore Washington Intl. Thurgood Marshall Airport (BWI). It's the main airport servicing this city and is located around 30 miles west of the downtown area. Once you've collected your suitcase, it won't be long before you're exploring the best of Chestertown.
How much is a flight to Chestertown?
Lots of sensational deals were picked up this week, with round-trip flights to Chestertown fluctuating between $97 and $122. But it was travelers beginning their trip from Fort Lauderdale (FLL) who scored the top bargains. One-way fares to Chestertown fell to a low $55.
How to book the cheapest flight to Chestertown?
Picking up cheap flights to Chestertown is as easy as booking your ticket with Orbitz. But if you want to make sure you're walking away with the best flight deals around, here are some suggestions to keep in mind:

  • Consider other airports to increase your savings. Enter your preferred departure and arrival points in the form fields, then select the 'Nearby airports' function below. It will list the available options.
  • If your travel plans aren't set in concrete, click on the 'Show flexible dates' option to compare flight deals across different departure dates. You may find an amazing fare.
  • You can also select the 'Show options' function to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you'd like to fly.
  • The early bird gets the most impressive deals, so book as soon as you know your travel dates. The cheapest fares get snapped up first and prices increase as the departure date gets closer.
  • Save big on your adventure by bundling your flights, hotels and car rental into a package. Your travel budget will thank you for it.
  • Flying during the busy season can mean expensive airfares. Try to travel outside of popular dates, such as Easter, Thanksgiving and school breaks.

How long is a flight to Chestertown?
Flight lengths depend on where you're setting off from, whether that's the East Coast, the West Coast or anywhere else. Listed below are some of the major routes to Chestertown and average flight times:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 1 hour and 55 minutes
  • Orlando, FL (MCO-Orlando Intl.) to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 2 hours and 10 minutes
  • Boston, MA (BOS-Logan Intl.) to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 1 hour and 33 minutes

What is the best time to book a flight to Chestertown?
Catch a bargain and book your tickets to Chestertown in January. If you've missed this month, fear not. February and August often have low airfares as well. Just make sure you don't snooze on a sale though — cheap flights pop up and disappear in the click of a button!
What day of the week is the cheapest to book a flight to Chestertown?
When it comes to cheap airfares to Chestertown, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A fantastic flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Chestertown?
According to Orbitz data from 2020, Monday is normally the best day of the week for cheap flights to Chestertown. Tuesday also has budget-friendly fares while Saturday has the highest ticket prices. Even though leaving at the weekend may be more convenient, you'll have more money in your pocket to play with if you set off at the start of the week.
What is the cheapest month to fly to Chestertown?
We won't keep you guessing — according to Orbitz data, August is generally the cheapest month to fly. Perfect for those who want a weekend getaway or simply escape from it all before the weather turns. The costliest time to fly is the height of summer, with fares peaking in June.
Which airlines allow free cancellation?
We know that plans can change and flexibility matters. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll show you fares more flexible than candy in a hot car!
What do I need for the flight to Chestertown?
Flying doesn't have to be a drag. In fact it can be fun with a bit of pre-planning! Make your journey a relaxing one with these useful hints:

  • Whether you print it out at home or use an electronic one, you'll need your boarding pass to get on to the plane. You'll also need some kind of government-issued photo identification. If you're traveling internationally, make sure your passport is valid and you've checked visa requirements.
  • To keep you occupied on your short trip to Chestertown, download some new songs or restock the podcast library on your phone. Food can also be a welcome distraction while in the air, so maybe even bring some snacks.
  • Even if you're traveling when it's 90 degrees outside, take a warm top or scarf on board with you. Airplane cabins can get quite chilly!

How many direct flights are there to Chestertown?
With roughly 659 direct flights every month, you'll be flying straight into Chestertown and embarking on your next big adventure in no time. Some of the carriers that journey nonstop to Chestertown include Southwest Airlines, Spirit Airlines and Delta Air Lines. American Airlines, United Airlines and Frontier Airlines are some other well-known options.
How do I get cheap first-class/business deals to Chestertown?
There are ways of booking first or business-class fares to Chestertown that won't burn a hole through your budget. Claim a seat in the pointy end of the plane for less with these practical tips:

  • Flexibility isn't confined to yoga. Avoid locking in your travel dates so you can snap up more affordable airfares when a sale pops up.
  • Budget airlines offer first or business-class seats at a fraction of the normal price. Ditch the full-service carriers and fly with one these cheaper options.
  • Bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat up the front. You can also try upgrading with points earned through a flight rewards program.

How to get into Chestertown from the airport?
File out of the plane and then get into the driver's seat of a Baltimore Washington Intl. Thurgood Marshall Airport (BWI) car rental at Baltimore Washington Intl. Thurgood Marshall Airport (BWI). On-site outlet Hertz has a nice variety of vehicles to select from, so finding the perfect ride will be a cinch. Set your GPS and then drive around 30 miles east of BWI to reach the heart of Chestertown. Or, you could also use public transportation or take a taxi into town straight after you land and rent a vehicle from central Chestertown with one of our Chestertown car rentals.
What is the best time to go to Chestertown?
Chestertown is a lively place in February, March and October. If you plan to visit during these months, it would be wise to book in advance to ensure you land the greatest deals. Curious to know what the summertime's like in Chestertown? Average daily temperatures usually fluctuate between 70 ºF and 80 ºF. Like most destinations in the Northern Hemisphere, summertime starts June 20 here.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.