$151 Cheap flight deals from Philadelphia (ILG) to Chestertown (BWI)

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This Weekend's Flight Deals from Philadelphia to Chestertown

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jul 12 - Wed, Jul 15
PHL
Philadelphia Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$832 Roundtrip, found 4 days ago
$832
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Jul 12 from Philadelphia Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jul 15, priced at $832 found 4 days ago

Airfares from $151 One Way, $302 Round Trip from Philadelphia to Chestertown

Prices starting at $302 for return flights and $151 for one-way flights to Chestertown were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 5 - Sun, Aug 9
PHL
Philadelphia
BWI
Baltimore
$302 Roundtrip, found 5 days ago
$302
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 5 from Philadelphia to Baltimore, returning Sun, Aug 9, priced at $302 found 5 days ago
Wed, Aug 19 - Sat, Aug 22
PHL
Philadelphia
BWI
Baltimore
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 19 from Philadelphia to Baltimore, returning Sat, Aug 22, priced at $306 found 5 days ago
Wed, Aug 5 - Sun, Aug 9
PHL
Philadelphia
BWI
Baltimore
$307 Roundtrip, found 5 days ago
$307
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 5 from Philadelphia to Baltimore, returning Sun, Aug 9, priced at $307 found 5 days ago
Wed, Aug 19 - Sat, Aug 22
PHL
Philadelphia
BWI
Baltimore
$311 Roundtrip, found 5 days ago
$311
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 19 from Philadelphia to Baltimore, returning Sat, Aug 22, priced at $311 found 5 days ago
Wed, Aug 5 - Mon, Aug 17
PHL
Philadelphia
BWI
Baltimore
$313 Roundtrip, found 5 days ago
$313
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 5 from Philadelphia to Baltimore, returning Mon, Aug 17, priced at $313 found 5 days ago

Chestertown economy flight packages

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach
2.5-star property

Gold Leaf Hotel of Dewey - Rehoboth Beach

8.8/10 Excellent! (1,018 reviews)

Aug 14 - Aug 16

2 night stay

Philadelphia (PHL) to Salisbury (SBY)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $739, price is now $643 per person
$643
per person
found 1 day ago
Somewhat clean property. Just a hotel to sleep and shower in. Location is its only plus. Parking garage was too small and hard to park. Shower and beds were basic. I didn’t appreciate being put in the front of the parking lot on the first floor. Super noisy. Cleaning staff were friendly. Won’t be coming back to this location as it was overpriced like all the other hotels in the area for summer.

Reviewed on Jul 5, 2026

Fenwick Shores, Tapestry Collection by Hilton
3.5-star property

Fenwick Shores, Tapestry Collection by Hilton

9.4/10 Exceptional! (784 reviews)

Aug 14 - Aug 16

2 night stay

Philadelphia (PHL) to Salisbury (SBY)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,091, price is now $836 per person
$836
per person
found 1 day ago
Multiple times no front desk staff available, Internet service EXTREMELY poor, which is unacceptable given the price of the room. Also main restaurant closed and “free breakfast “ which was pre paid came from the bar. Room also looks much better on the website than in person. Not fully clean, hairs on bathroom floor from last person. On the plus side bar staff was very nice . Outdoor pool appeared clean.

Reviewed on Jul 4, 2026

Home2 Suites by Hilton Lewes Rehoboth Beach
3.0-star property

Home2 Suites by Hilton Lewes Rehoboth Beach

9.4/10 Exceptional! (1,000 reviews)

Aug 14 - Aug 16

2 night stay

Philadelphia (PHL) to Salisbury (SBY)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $766, price is now $666 per person
$666
per person
found 1 day ago
Good hotel

Reviewed on Jul 6, 2026

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More About Flying To Chestertown from Philadelphia

Route Information for Flights from Philadelphia to Chestertown

Origin Airport IATA Code
ILG
Destination Airport IATA Code
BWI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Philadelphia to Chestertown

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.