Search Cheap Flights toChestertown
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Chestertown Flights as Low as $62
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, May 31 - Wed, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$62 Roundtrip, found 21 hours ago
$62
Roundtrip
found 21 hours ago
Sat, May 31 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Tue, Jun 3 - Sun, Jun 8
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$76 Roundtrip, found 9 hours ago
$76
Roundtrip
found 9 hours ago
Wed, Jun 11 - Wed, Jun 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$77 Roundtrip, found 6 hours ago
$77
Roundtrip
found 6 hours ago
Sat, May 31 - Wed, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$78 Roundtrip, found 21 hours ago
$78
Roundtrip
found 21 hours ago
Sat, May 31 - Wed, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$83 Roundtrip, found 21 hours ago
$83
Roundtrip
found 21 hours ago
Sun, Jun 1 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
Thu, May 29 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Tue, Jun 3 - Mon, Jun 9
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Wed, May 28 - Thu, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$92 Roundtrip, found 6 days ago
$92
Roundtrip
found 6 days ago
Tue, Jun 17 - Wed, Jun 18
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Wed, Jun 11 - Wed, Jun 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$162 Roundtrip, found 6 hours ago
$162
Roundtrip
found 6 hours ago
Wed, Jun 11 - Wed, Jun 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$181 Roundtrip, found 6 hours ago
$181
Roundtrip
found 6 hours ago
Fri, Jul 11 - Sat, Jul 12
IAH
George Bush Intercontinental
BWI
Baltimore Washington Intl. Thurgood Marshall
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Thu, May 29 - Sat, May 31
PHX
Sky Harbor Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$223 Roundtrip, found 4 days ago
$223
Roundtrip
found 4 days ago
Wed, Aug 20 - Tue, Aug 26
PHX
Sky Harbor Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$296 Roundtrip, found 1 day ago
$296
Roundtrip
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 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 $62, 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 $62 right now, why wait?
Destination airport | Baltimore Washington Intl. Thurgood Marshall |
Destination airport IATA code | BWI |
Roundtrip price | $62 |
Last Minute Hotel Deals in Chestertown
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! (354 reviews)
"Very accommodating and polite staff"
Reviewed on May 20, 2025
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! (763 reviews)
"Traveled for daughters volleyball tournament at the college"
Reviewed on May 5, 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! (49 reviews)
"Wonderful quiet place. Enjoyed our night."
Reviewed on Apr 27, 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! (1,776 reviews)
"Beautiful hotel near everything"
Reviewed on May 17, 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! (1,004 reviews)
"I Absolutely loved this hotel!!! Beautiful !!!"
Reviewed on May 18, 2025
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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 ...
6.8/10 (1,009 reviews)
"Monique the manager was amazing great customer service."
Reviewed on May 13, 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! (1,001 reviews)
"Excellent!"
Reviewed on May 13, 2025
Hampton Inn Baltimore/Glen Burnie
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 ...
8/10 Very Good! (1,012 reviews)
"Convenient location. Great restaurants and shopping nearby. Staff are great. Place is clean, relatively well maintained. Love the free breakfast and the 24/7 hot beverage bar in the lobby."
Reviewed on May 18, 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
- Best Western Plus Hotel & Conference Center
- La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
- Sagamore Pendry Baltimore
- Hampton Inn Baltimore/Glen Burnie
- Hilton Garden Inn Baltimore/White Marsh
- Hampton Inn Baltimore/White Marsh
- Hampton Inn Baltimore Bayview Campus
- Annapolis Waterfront Hotel, Autograph Collection
- Fairfield Inn & Suites by Marriott White Marsh
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Quality Inn & Suites Bel Air I-95 Exit 77A