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Chestertown

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Chestertown Flights as Low as $66

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

Frontier Airlines
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 5, priced at $66 found 1 day ago
Frontier Airlines
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 5 hours ago
$68
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 2, priced at $68 found 5 hours ago
Frontier Airlines
Fri, Apr 24 - Sat, Apr 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 24 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Apr 25, priced at $68 found 1 day ago
Frontier Airlines
Thu, Apr 30 - Tue, May 5
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 5, priced at $72 found 1 day ago
Frontier Airlines
Thu, Apr 9 - Thu, Apr 16
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Apr 16, priced at $73 found 1 day ago
Frontier Airlines
Wed, Apr 22 - Wed, May 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$74 Roundtrip, found 5 hours ago
$74
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, May 6, priced at $74 found 5 hours ago
Spirit Airlines
Wed, Apr 22 - Sun, May 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Apr 22 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 10, priced at $117 just found
Breeze Airways
Mon, Jul 27 - Wed, Jul 29
MCO
Orlando Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Jul 27 from Orlando Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jul 29, priced at $142 found 1 day ago
Frontier Airlines
Wed, Apr 22 - Sat, Apr 25
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$160 Roundtrip, found 21 hours ago
$160
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Apr 25, priced at $160 found 21 hours ago
Delta
Wed, Apr 22 - Wed, May 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$265 Roundtrip, found 5 hours ago
$265
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Apr 22 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, May 6, priced at $265 found 5 hours ago
Bargain Flight
Mon, Mar 30 - Mon, Apr 6
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$272 Roundtrip, found 2 days ago
$272
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Mar 30 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Apr 6, priced at $272 found 2 days ago
American Airlines
Tue, May 5 - Tue, May 5
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 5 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 5, priced at $275 found 2 days ago
Alaska Airlines
Wed, Apr 22 - Tue, May 5
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$373 Roundtrip, found 3 days ago
$373
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 5, priced at $373 found 3 days ago
Sun Country Airlines
Thu, Jul 23 - Mon, Jul 27
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$463 Roundtrip, found 1 day ago
$463
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Jul 23 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Jul 27, priced at $463 found 1 day ago
American Airlines
Wed, Apr 29 - Tue, May 5
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$490 Roundtrip, found 16 hours ago
$490
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Tue, May 5, priced at $490 found 16 hours ago
American Airlines
Fri, May 15 - Wed, May 27
LAX
Los Angeles Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$688 Roundtrip, found 1 day ago
$688
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, May 15 from Los Angeles Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, May 27, priced at $688 found 1 day 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 April, 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 15 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 $66, 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 $66 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$66

Last Minute Hotel Deals in Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
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 ...
8.6/10 Excellent! (892 reviews)
Clean and helpful

Reviewed on Mar 27, 2026

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Comfort Inn & Suites Chestertown
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
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 ...
9/10 Wonderful! (1,863 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.

Reviewed on Mar 24, 2026

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Historic Inns of Annapolis
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
Book a stay at this business-friendly hotel in Glen Burnie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,002 reviews)
Nice clean rooms and staff. Good location

Reviewed on Mar 25, 2026

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Hampton Inn Baltimore/Glen Burnie
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
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 ...
7/10 Good! (1,182 reviews)
So a couple of years back when my wife and I stayed here it was pretty decent. Not sure what has happened as of late, but the elevator doesn't work, the breakfast was less than average and there are prostitutes housed at the location. Had I known, I wouldn't have booked the place.

Reviewed on Mar 27, 2026

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La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Book a stay at this 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! (1,001 reviews)
Great hotel!

Reviewed on Mar 27, 2026

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Pendry Baltimore
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
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 ...
7.8/10 Good! (1,005 reviews)
Nice and and courteous, friendly staff very clean, great entertainment at the comedy factor and nightclub within facility great breakfast bar .

Reviewed on Mar 27, 2026

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Best Western Plus Hotel & Conference Center
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (912 reviews)
I would have given an excellent but there was still some renovations being done. Staff was great, rooms were beautiful and clean. Location is perfect and within walking distance to tons of shops, restaurants and bars. Their restaurant was currently closed for remodeling but guests can still get room ...

Reviewed on Mar 20, 2026

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Annapolis Waterfront Hotel, Autograph Collection
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Book a stay at this family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,001 reviews)
the rooms were decent for the price. the staff was professional and inviting. the pool however was noy desirable at all. my kids didnt want to be in it as well as the hot tub. The purpose of the trip was to get the kids out play in the pool so that was a little upsetting. other than that its a nice ...

Reviewed on Mar 18, 2026

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Hilton Garden Inn Baltimore/White Marsh
See all 1,088 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.