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Chestertown

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Chestertown Flights as Low as $87

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

Spirit Airlines
Tue, Sep 9 - Tue, Sep 9
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Sep 9 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 9, priced at $87 found 1 day ago
Spirit Airlines
Wed, Sep 10 - Wed, Sep 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 1 day ago
$88
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 10, priced at $88 found 1 day ago
Frontier Airlines
Fri, Sep 12 - Sun, Sep 14
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 14, priced at $94 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Sun, Sep 7
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$100 Roundtrip, found 4 days ago
$100
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 7, priced at $100 found 4 days ago
Spirit Airlines
Fri, Sep 12 - Sun, Sep 14
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Sep 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 14, priced at $104 found 1 day ago
Frontier Airlines
Mon, Aug 25 - Mon, Sep 1
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 1, priced at $110 found 1 day ago
Frontier Airlines
Sun, Aug 31 - Mon, Sep 1
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Aug 31 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 1, priced at $110 found 1 day ago
Spirit Airlines
Sat, Sep 13 - Sat, Sep 13
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 13, priced at $112 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Sun, Sep 7
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Sep 7, priced at $114 found 4 days ago
Frontier Airlines
Fri, Sep 5 - Thu, Sep 11
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$116 Roundtrip, found 6 days ago
$116
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Sep 11, priced at $116 found 6 days ago
Frontier Airlines
Mon, Sep 8 - Thu, Sep 11
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Sep 8 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Sep 11, priced at $119 found 6 days ago
Delta
Sat, Aug 30 - Sun, Aug 31
MSN
Dane County Regional
BWI
Baltimore Washington Intl. Thurgood Marshall
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 30 from Dane County Regional to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Aug 31, priced at $221 found 2 days ago
American Airlines
Sat, Dec 13 - Sat, Dec 13
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$223 Roundtrip, found 4 days ago
$223
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Dec 13 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Dec 13, priced at $223 found 4 days ago
United
Sat, Aug 30 - Tue, Sep 2
MSN
Dane County Regional
BWI
Baltimore Washington Intl. Thurgood Marshall
$257 Roundtrip, found 1 hour ago
$257
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Aug 30 from Dane County Regional to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 2, priced at $257 found 1 hour ago
Delta
Tue, Oct 7 - Tue, Oct 14
CAE
Columbia Metropolitan
BWI
Baltimore Washington Intl. Thurgood Marshall
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 7 from Columbia Metropolitan to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 14, priced at $262 found 1 day ago
American Airlines
Tue, Sep 30 - Wed, Oct 8
CAE
Columbia Metropolitan
SBY
Salisbury - Ocean City Wicomico Regional
$411 Roundtrip, found 4 days ago
$411
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 30 from Columbia Metropolitan to Salisbury - Ocean City Wicomico Regional, returning Wed, Oct 8, priced at $411 found 4 days 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 September, 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 $87, 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 $87 right now, why wait?

Chestertown Flight Information
Destination airport
Baltimore Washington Intl. Thurgood Marshall
Destination airport IATA code
BWI
Roundtrip price
$86

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 ...
8.4/10 Very Good! (794 reviews)
"FEELS LIKE PEACEFULLY 👍 👌"

Reviewed on Aug 14, 2025

Get rates
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! (386 reviews)
"Great service"

Reviewed on Aug 1, 2025

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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
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 ...
8/10 Very Good! (60 reviews)
"They've definitely spent a lot of money."

Reviewed on Aug 10, 2025

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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 ...
8.8/10 Excellent! (1,823 reviews)
"Lovely room. Comfortable bed."

Reviewed on Aug 13, 2025

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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 ...
8/10 Very Good! (1,000 reviews)
"Everything was amazing"

Reviewed on Aug 9, 2025

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Hampton Inn Baltimore/Glen Burnie
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
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 ...
9.2/10 Wonderful! (1,001 reviews)
"Staying at the Sagamore Pendry had been on my bucket list for years, and I finally made it happen for a special anniversary. The hotel is undeniably elegant, with exceptional staff and a clean, well-maintained atmosphere that reflects its historic charm. However, I couldn’t help but feel underwhelmed ..."

Reviewed on Aug 14, 2025

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Sagamore Pendry Baltimore
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,002 reviews)
"Very nice room, clean and comfortable. Great value for a one night stay on a road trip."

Reviewed on Aug 10, 2025

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Quality Inn & Suites Bel Air I-95 Exit 77A
Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

3 out of 5
1803 Porter Street, Baltimore, MD
Stay at this 3-star business-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (643 reviews)
"McHenry Row is amazing. The hotel was within walki g distance to the cruise port which was convenient."

Reviewed on Aug 14, 2025

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Courtyard by Marriott Baltimore Downtown/McHenry Row
See all 1,074 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.