Search Cheap Flights toChestertown
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Chestertown Flights as Low as $72
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Jun 17 - Sat, Jun 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 11 hours ago
$72
Roundtrip
found 11 hours ago
Wed, Jul 16 - Thu, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$79 Roundtrip, found 9 hours ago
$79
Roundtrip
found 9 hours ago
Tue, Oct 7 - Tue, Oct 7
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$86 Roundtrip, found 6 hours ago
$86
Roundtrip
found 6 hours ago
Tue, Jul 15 - Thu, Jul 24
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$91 Roundtrip, found 13 hours ago
$91
Roundtrip
found 13 hours ago
Tue, Jun 17 - Sat, Jun 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$93 Roundtrip, found 11 hours ago
$93
Roundtrip
found 11 hours ago
Sat, Jun 14 - Tue, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$94 Roundtrip, found 6 days ago
$94
Roundtrip
found 6 days ago
Mon, Jun 16 - Tue, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$95 Roundtrip, found 1 day ago
$95
Roundtrip
found 1 day ago
Tue, Jul 15 - Sat, Jul 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Sun, Jun 15 - Tue, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Tue, Jul 15 - Tue, Oct 7
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Tue, Aug 12 - Tue, Aug 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$129 Roundtrip, found 13 hours ago
$129
Roundtrip
found 13 hours ago
Tue, Oct 7 - Tue, Oct 7
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Wed, Aug 13 - Wed, Aug 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Tue, Jul 15 - Tue, Oct 7
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Mon, Jun 16 - Mon, Jun 30
LEX
Blue Grass
BWI
Baltimore Washington Intl. Thurgood Marshall
$246 Roundtrip, found 22 hours ago
$246
Roundtrip
found 22 hours ago
Wed, Jul 23 - Sun, Jul 27
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$450 Roundtrip, found 5 hours ago
$450
Roundtrip
found 5 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 June, 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 $72, 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 $72 right now, why wait?
Destination airport | Baltimore Washington Intl. Thurgood Marshall |
Destination airport IATA code | BWI |
Roundtrip price | $72 |
Last Minute Hotel Deals in Chestertown
Comfort Inn & Suites Chestertown
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 ...
8.4/10 Very Good! (770 reviews)
"The grass and landscape was not maintained"
Reviewed on Jun 4, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
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! (366 reviews)
"Clean, spacious, affordable accommodations."
Reviewed on Jun 3, 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
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 ...
7.8/10 Good! (50 reviews)
"Absolutely loved our stay here! The staff were so kind and accommodating. The room was very clean and bed was comfortable. Jellee Fish Joel's (the beach bar) just received a huge makeover and we had a blast! we will be back again soon!"
Reviewed on Jun 2, 2025
Historic Inns of Annapolis
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 ...
8.8/10 Excellent! (1,782 reviews)
"Nice place, close to every thing, so nice staff an good value for money"
Reviewed on Jun 7, 2025
Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
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! (1,004 reviews)
"Great hotel absoultely stunning qnd the people there so nice"
Reviewed on Jun 4, 2025
Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard, Baltimore, MD
Stay at this 3-star 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)
"Curious ,polite staff."
Reviewed on Jun 6, 2025
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
2112b Emmorton Park Rd, Edgewood, MD
Stay at this 3-star hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8/10 Very Good! (1,002 reviews)
"Clean and friendly staff."
Reviewed on Jun 8, 2025
Best Western Plus Hotel & Conference Center
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 ...
7.6/10 Good! (1,000 reviews)
"Friendly services"
Reviewed on Jun 7, 2025
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.
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Top Chestertown Hotels
- Comfort Inn & Suites Chestertown
- Historic Inns of Annapolis
- Sagamore Pendry Baltimore
- Hilton Garden Inn Baltimore/White Marsh
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Best Western Plus Hotel & Conference Center
- Quality Inn & Suites Bel Air I-95 Exit 77A
- Hampton Inn Baltimore/White Marsh
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
- Fairfield Inn & Suites by Marriott White Marsh
- Hampton Inn Baltimore/Glen Burnie