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Chestertown

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Chestertown Flights as Low as $60

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

Frontier Airlines
Wed, Jun 24 - Tue, Jun 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 5 hours ago
$60
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Jun 24 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 30, priced at $60 found 5 hours ago
Frontier Airlines
Mon, Jun 1 - Tue, Jun 16
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$61 Roundtrip, found 19 hours ago
$61
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Jun 1 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 16, priced at $61 found 19 hours ago
Frontier Airlines
Sat, Jun 6 - Tue, Jun 9
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$63 Roundtrip, found 14 hours ago
$63
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 9, priced at $63 found 14 hours ago
Frontier Airlines
Tue, Jun 23 - Tue, Jun 30
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$69 Roundtrip, found 18 hours ago
$69
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Tue, Jun 23 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jun 30, priced at $69 found 18 hours ago
Frontier Airlines
Tue, Jun 16 - Wed, Jun 24
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 17 hours ago
$70
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Jun 16 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jun 24, priced at $70 found 17 hours ago
Frontier Airlines
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 15 hours ago
$88
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 2, priced at $88 found 15 hours ago
Breeze Airways
Wed, Jun 3 - Wed, Jun 10
MCO
Orlando Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$125 Roundtrip, found 23 hours ago
$125
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Jun 3 from Orlando Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jun 10, priced at $125 found 23 hours ago
Frontier Airlines
Thu, Jul 9 - Tue, Jul 14
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$230 Roundtrip, found 22 hours ago
$230
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Thu, Jul 9 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 14, priced at $230 found 22 hours ago
Delta
Tue, Jun 16 - Tue, Jul 7
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$247 Roundtrip, found 9 hours ago
$247
Roundtrip
found 9 hours ago
Select Delta flight, departing Tue, Jun 16 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 7, priced at $247 found 9 hours ago
United
Wed, Aug 19 - Wed, Sep 2
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 19 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 2, priced at $257 found 1 day ago
American Airlines
Tue, Jun 16 - Tue, Jul 7
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$257 Roundtrip, found 9 hours ago
$257
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Jun 16 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 7, priced at $257 found 9 hours ago
JetBlue Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$363 Roundtrip, found 15 hours ago
$363
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Wed, Aug 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 2, priced at $363 found 15 hours ago
Alaska Airlines
Thu, Jul 9 - Tue, Jul 14
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$524 Roundtrip, found 22 hours ago
$524
Roundtrip
found 22 hours ago
Select Alaska Airlines flight, departing Thu, Jul 9 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 14, priced at $524 found 22 hours ago
Sun Country Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$528 Roundtrip, found 1 day ago
$528
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jul 25, priced at $528 found 1 day ago
American Airlines
Tue, May 26 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$590 Roundtrip, found 4 days ago
$590
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, May 26 from Hartsfield-Jackson Atlanta Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Jun 3, priced at $590 found 4 days ago
American Airlines
Fri, Oct 9 - Wed, Oct 21
LAX
Los Angeles Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$696 Roundtrip, found 1 day ago
$696
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 9 from Los Angeles Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Oct 21, priced at $696 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 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 $60, 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 $60 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$59

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! (909 reviews)
Traveling on 301 to New England somewhat off the beaten path Service excellent

Reviewed on Apr 28, 2026

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Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
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! (440 reviews)
Clean lady was nice help me out

Reviewed on Apr 26, 2026

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Red Roof 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
Book a stay at this 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! (80 reviews)
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, ...

Reviewed on Apr 23, 2026

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The Lodge at Great Oak Landing
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! (1,851 reviews)
Staff were great! Very friendly. Setting is terrific. We loved our king bed room. Thanks!

Reviewed on May 8, 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! (1,007 reviews)
The woman who staffed the breakfast area was extremely helpful. She was friendly and went out of her way to make travellers comfortable.

Reviewed on May 10, 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! (1,198 reviews)
The room wasnt clean. Tub wasnt thoroughly clean. Saw roahes. Next door room dog barked all night. Just wasn't an comfortable stay

Reviewed on May 9, 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! (1,007 reviews)
My friend and I stayed here as a weekend getaway. It was absolutely perfect. The service was phenomenal from start to finish. We did have an issue with valet but they corrected it immediately and gave us a discount on the cost. The hotel is stunning, lives up to all the hype.

Reviewed on May 4, 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)
Breakfast

Reviewed on May 7, 2026

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Best Western Plus Hotel & Conference Center
See all 1,090 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.