Cheap Flights To Chestertown 2026

Chestertown Flights as Low as $118

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Thu, Oct 22 - Wed, Oct 28
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$129
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 28, priced at $129 found 5 days ago
Frontier Airlines
Tue, Oct 20 - Tue, Oct 27
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$135
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 27, priced at $135 found 5 days ago
Frontier Airlines
Tue, Oct 20 - Tue, Nov 3
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$138
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 3, priced at $138 found 5 days ago
Frontier Airlines
Wed, Oct 14 - Wed, Oct 28
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$139
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 28, priced at $139 found 5 days ago
Frontier Airlines
Tue, Oct 20 - Thu, Oct 22
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$140
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Oct 22, priced at $140 found 5 days ago
Frontier Airlines
Frontier Airlines
Thu, Oct 22 - Tue, Nov 3
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$143
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Nov 3, priced at $143 found 5 days ago
Frontier Airlines
Wed, Oct 14 - Tue, Oct 27
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$150
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Oct 27, priced at $150 found 5 days ago
Breeze Airways
Wed, Oct 21 - Wed, Oct 28
MCO
Orlando Intl.
SBY
Salisbury - Ocean City Wicomico Regional
$152
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Oct 21 from Orlando Intl. to Salisbury - Ocean City Wicomico Regional, returning Wed, Oct 28, priced at $152 found 8 hours ago
Frontier Airlines
Wed, Oct 14 - Thu, Oct 29
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$153
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Oct 29, priced at $153 found 5 days ago
Southwest Airlines
Delta
Mon, Jan 11 - Sat, Jan 16
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$279
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jan 11 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jan 16, priced at $279 found 3 days ago
American Airlines
United
Thu, Jan 14 - Sun, Jan 17
JAX
Jacksonville Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$382
Roundtrip
found 3 days ago
Select United flight, departing Thu, Jan 14 from Jacksonville Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jan 17, priced at $382 found 3 days ago
JetBlue Airways
Sat, Nov 7 - Thu, Dec 31
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$505
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Sat, Nov 7 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Dec 31, priced at $505 found 18 hours ago

Flights to

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to . AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. With the best rates from Expedia combined with members-only discounts, AARP Travel offers members the best price in travel, guaranteed.

As an AARP member, you'll have the opportunity to take advantage of exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

Whether this trip is for business or pleasure–we will help you get there (without breaking the bank).

Transportation at the Airport

Once you've got your flight scheduled to , you might want to book a rental car so you can get around on your own. You can request a rental car under our cars tab and hop in the car as soon as you step out of the airport. For more information, check out the Chestertown Car Rentals Guide.

Activities

If you aren't sure where to start, we can help you with that as well. Not to worry—there's so many things to do in this city. No matter what you decide to do with your time, you're sure to have fun in this city.

If you're looking for some fun activities to do in , make sure you look at our "Things to Do in Chestertown" page for activities and excursions for the whole clan.

Where to Stay in

has lodging options in the area, so you'll have no trouble finding a place to stay close to all the things you want to see. If you need to stay close to the airport, or another attraction in , check out our hotel listings page. No matter where you stay, just remember that you will get the best for your visit to when you book your stay with AARP.

Book Your Trip Now

Once you have planned your travel dates, allow us here at AARP Travel to connect you with inexpensive tickets to . Don't wait a second longer—book your airfare today and land in tomorrow.