Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


How Much Does It Cost To Fly To Chestertown?

The cheapest tickets to Chestertown available within the past 7 days were $97. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Chestertown Flights

You've got an appetite for adventure, but this time you need more than the classic staycation. You need more than what the city next door has going on. It's about time to take to the heavens, and you'll soon find yourself in a distant city. We're here for you, with a huge selection of flights to Chestertown! Thanks to our cheap plane tickets, you'll have money left over for all of Chestertown's fabulous eateries, shopping, and nightlife. Once your next trip is being planned, put your faith in Expedia.com.

Can't-Miss Chestertown Experiences

You're the sort of trip-taker who jumps into action as soon as possible. We totally know how you feel. There's a reason you've decided to float over to Chestertown, where you will have lots of things to see and do. Start by checking out our guide to activities for Chestertown and see for yourself.

Choices for Lodging Near the Airport

Prefer to have a nap before seeing your new neck of the woods? Luck is on your side. When you search our database of 2 Chestertown hotels, all the courtesies you want are within reach. Book like a pro, and book at one of our airport hotels near Chestertown close to the runway.

Now Is the Time to Visit!

  • We have flights as affordable as $97, and you can save even more when you add one of our Chestertown hotels to your flight in a packaged deal!
  • The number of travelers flying here is growing reserve your ticket now!

Say farewell to your office mates, load your gear, and make your way to Chestertown! Believe another travel company can surpass Expedia.com when it comes to Chestertown flights? Think again. Our pricing and selection are simply amazing. Why wait any longer? It's time to get ahold of affordable airfares and see the town up close and personal.

Expedia.com lets you search across the largest number of airlines and Chestertown flights, which means that you'll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia.com do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chestertown flight!

Browse through dozens of options and rest assured that you're seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chestertown trip. There's simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Chestertown flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights to Chestertown with Expedia.com. Use us as your stop travel destination and have the confidence that you're getting a bargain!

Reviews from verified customers

May 19, 2019

Small delay, just over 30’

May 18, 2019

Our flight attendant whose name was Joshua Amos was absolutely amazing! He was not only cheerful and friendly. You could tell that he genuinely enjoys his job and was having fun serving the passengers. In turn, it was probably the most fun and entertaining flight that I have ever been on. I fly a great deal and jope that I am blessed to be on another "Joshua Amos" flight in the future! Can you clone him pleeeeease?

May 18, 2019

Only problem was that after boarding we were told we would be taking off in less than 10 minutes. Then we were told they were turning off the power for 2 minutes. We didn't hear anything else for over 30 minutes. Updates would have been nice.

May 18, 2019

Nice flight

May 17, 2019

A good all around experience

May 10, 2019

I did pay extra for a specific seat to be next to a family member and my seat was changed. I feel if you pay extra for a specific seat, it shouldn't be taken from you. In the end it did work out but I was disappointed with the situation.

May 5, 2019

Give free snacks or water

May 5, 2019

Rows WAY too close together; difficult to enter & exit, not enough leg room

May 2, 2019

The best flight ever!!!! I normally afraid of flights specially when preparing for landing due to turbulence and the the plane tends to shake a lot but on this flight it was totally smooth landing. Thank you Pilots

May 2, 2019

We waited at check-in when there seemed to be available staff to help. Also, it took a while to get my stroller and car seat and there didn't seem to be enough time between pre-boarding (boarding with an infant) and general boarding. We weren't settled before there was a backup of people boarding.