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Chestertown

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Chestertown Flights as Low as $84

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

Spirit Airlines
Wed, May 7 - Tue, May 20
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, May 7 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 20, priced at $84 found 2 days ago
Spirit Airlines
Fri, Apr 25 - Tue, Apr 29
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$91 Roundtrip, found 5 hours ago
$91
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Fri, Apr 25 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Apr 29, priced at $91 found 5 hours ago
Spirit Airlines
Wed, May 7 - Mon, May 12
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, May 7 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, May 12, priced at $96 found 2 days ago
Spirit Airlines
Fri, May 9 - Tue, May 20
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, May 9 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 20, priced at $97 found 2 days ago
Spirit Airlines
Sat, May 10 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, May 10 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 11, priced at $98 found 2 days ago
Spirit Airlines
Fri, Apr 25 - Tue, Apr 29
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$101 Roundtrip, found 5 hours ago
$101
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Fri, Apr 25 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Apr 29, priced at $101 found 5 hours ago
Spirit Airlines
Wed, Apr 16 - Wed, Apr 23
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$102 Roundtrip, found 16 hours ago
$102
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Apr 16 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Apr 23, priced at $102 found 16 hours ago
Spirit Airlines
Tue, Apr 15 - Mon, Apr 28
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$103 Roundtrip, found 3 days ago
$103
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Apr 15 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Apr 28, priced at $103 found 3 days ago
Spirit Airlines
Thu, May 8 - Mon, May 12
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, May 8 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, May 12, priced at $108 found 2 days ago
Frontier Airlines
Sat, May 10 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 10 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 11, priced at $210 found 2 days ago
Delta
Sat, May 10 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, May 10 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 11, priced at $217 found 2 days ago
American Airlines
Sat, May 10 - Sun, May 11
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, May 10 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 11, priced at $219 found 2 days ago
American Airlines
Thu, Apr 17 - Mon, Apr 21
BDL
Bradley Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$380 Roundtrip, found 1 day ago
$380
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Apr 17 from Bradley Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Apr 21, priced at $380 found 1 day ago
American Airlines
Sat, Jun 21 - Tue, Jun 24
BDL
Bradley Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$462 Roundtrip, found 9 hours ago
$462
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sat, Jun 21 from Bradley Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, Jun 24, priced at $462 found 9 hours ago
United
Fri, Apr 25 - Tue, Apr 29
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$475 Roundtrip, found 5 hours ago
$475
Roundtrip
found 5 hours ago
Select United flight, departing Fri, Apr 25 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Apr 29, priced at $475 found 5 hours ago
American Airlines
Sat, Jul 19 - Sat, Jul 26
FLL
Fort Lauderdale - Hollywood Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$570 Roundtrip, found 9 hours ago
$570
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sat, Jul 19 from Fort Lauderdale - Hollywood Intl. to Salisbury - Ocean City Wicomico Regional, returning Sat, Jul 26, priced at $570 found 9 hours ago

Cheap Flights to Chestertown

Fall in love at first flight with your vacation to Chestertown by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chestertown on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chestertown, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chestertown

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chestertown with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BWI airport.

What is the cheapest month to fly to Chestertown?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chestertown are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chestertown?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chestertown.

What airport is best to fly into Chestertown?

When you’re planning your trip to Chestertown, convenience is the name of the game. Luckily, Chestertown Martin State Airport is nearby so you can deplane and get going on checking off everything on your Chestertown must-do list.

How much are flights to Chestertown?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chestertown on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $84, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chestertown?

The trick to saving a stack of cash on your flight to Chestertown? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $84 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$102

Last Minute Hotel Deals in Chestertown

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is $76 per night from Apr 16 to Apr 17
$76
includes taxes & fees
Apr 16 - Apr 17
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (343 reviews)
"I stayed here one night and got a stripper pregnant. 10/10 will book again."

Reviewed on Apr 4, 2025

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $115 per night from Apr 20 to Apr 21
$115
includes taxes & fees
Apr 20 - Apr 21
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (754 reviews)
"Check-in was quick & easy. The gentleman at the desk was wonderfully pleasant and very welcoming. Our room was clean and spacious. Beds were clean and comfortable."

Reviewed on Apr 4, 2025

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
The price is $133 per night from Apr 13 to Apr 14
$133
includes taxes & fees
Apr 13 - Apr 14
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.6/10 Good! (47 reviews)
Respite
"Generally okay, Clean but property could use some upgrade"

Reviewed on Oct 27, 2024

The Lodge at Great Oak Landing
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is $199 per night from Apr 16 to Apr 17
$199
includes taxes & fees
Apr 16 - Apr 17
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,738 reviews)
"Great location, easy, quick check in. Front desk staff was very friendly and professional. I would choose this property for future travel."

Reviewed on Apr 8, 2025

Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4 out of 5
80 Compromise St, Annapolis, MD
The price is $218 per night from Apr 20 to Apr 21
$218
includes taxes & fees
Apr 20 - Apr 21
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (808 reviews)
"Good"

Reviewed on Mar 23, 2025

Annapolis Waterfront Hotel, Autograph Collection
Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center
2.5 out of 5
5625 O'Donnell Street, Baltimore, MD
The price is $110 per night from Apr 20 to Apr 21
$110
includes taxes & fees
Apr 20 - Apr 21
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,002 reviews)
Love this Hotel
"Safe hotel, great neighborhood. Great breakfast"

Reviewed on Apr 6, 2025

Best Western Plus Hotel & Conference Center
Sagamore Pendry Baltimore
Sagamore Pendry Baltimore
5 out of 5
1715 Thames St., Baltimore, MD
The price is $427 per night from Apr 22 to Apr 23
$427
includes taxes & fees
Apr 22 - Apr 23
Stay at this 5-star luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,002 reviews)
"Our favorite home away from home."

Reviewed on Apr 7, 2025

Sagamore Pendry Baltimore
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
The price is $93 per night from Apr 13 to Apr 14
$93
includes taxes & fees
Apr 13 - Apr 14
Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
6.8/10 (1,005 reviews)
"Had to be careful as there was no non-slip bath mat for safety"

Reviewed on Apr 5, 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
See all 1,046 properties in 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.