Cheap Flights to Chester: Chester Flight Deals

View €52 flight on Thu, 27 Nov 2025Opens in a new window

Popular airlines to Chester

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Cheap round-trip flights to Chester

Prices were available within the past 7 days and start at €52 for one-way flights and €153 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, 26 Sept - Sun, 28 Sept
MCO
Orlando
SWF
Newburgh
€153 Return, found 4 days ago
€153
Return
found 4 days ago
Select Breeze Airways flight, departing Fri, 26 Sept from Orlando to Newburgh, returning Sun, 28 Sept, priced at €153 found 4 days ago
Breeze Airways
Thu, 2 Oct - Mon, 6 Oct
MCO
Orlando
SWF
Newburgh
€169 Return, found 23 hours ago
€169
Return
found 23 hours ago
Select Breeze Airways flight, departing Thu, 2 Oct from Orlando to Newburgh, returning Mon, 6 Oct, priced at €169 found 23 hours ago
Breeze Airways
Thu, 2 Oct - Mon, 6 Oct
MCO
Orlando
SWF
Newburgh
€170 Return, found 7 hours ago
€170
Return
found 7 hours ago
Select Breeze Airways flight, departing Thu, 2 Oct from Orlando to Newburgh, returning Mon, 6 Oct, priced at €170 found 7 hours ago
Breeze Airways
Mon, 29 Sept - Fri, 3 Oct
MCO
Orlando
SWF
Newburgh
€245 Return, found 4 days ago
€245
Return
found 4 days ago
Select Breeze Airways flight, departing Mon, 29 Sept from Orlando to Newburgh, returning Fri, 3 Oct, priced at €245 found 4 days ago

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Chester. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Chester. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Chester, or are just on the lookout for the best flights to Chester, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Chester to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Frequently asked questions

What is the name of Chester's airport?
John F. Kennedy Intl. Airport (JFK) is the most frequently used airport in Chester.
What airport is best to fly into Chester?
A great number of travellers fly in and out of Chester every day. With numerous airports servicing the city, there are a few places you might disembark. The main ones are John F. Kennedy Intl. Airport (JFK) (88 kilometres from downtown), EWR (72 kilometres from downtown) and LaGuardia Airport (LGA) (72 kilometres from downtown).
How many airlines fly to Chester?
There are 86 airlines that jet into Chester from 219 airports across the globe.
Which airlines fly to Chester?
United Airlines, American Airlines and Delta are the most frequent fliers to Chester. The majority of flights come in from Chicago, with United Airlines offering the most services on this route.
How many nonstop flights are there to Chester?
Organising an exciting Chester adventure is a piece of cake when there are 10,434 nonstop flights each week to get you there.
Where are the most popular flights to Chester departing from?
A large number of flights to Chester set off from Chicago, Orlando and Toronto airports.
How long is the flight to Chester Airport?
If it's Chicago you're leaving behind, you'll be midair for around 2 hours and 12 minutes before you touchdown in Chester. Terminal to terminal from Orlando typically takes 2 hours and 44 minutes and from Toronto, the flight time is 1 hour and 40 minutes.
How to book the cheapest flight to Chester?
We all know those jet-setters who somehow score incredibly cheap airfares wherever they go. Would you like to know how to do it for your Chester holiday? Don't leave it until the last possible moment to secure your flight. Also, do some online research and compare your options. If your destination has a few airports, you may be able to nab a terrific price by flying into a less busy terminal. And finally, remember that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to secure your seat as soon as you spot an unbeatable bargain. The best deals don't last long.
Do you have any tips for my flight to Chester?
Depending on where you're coming from, your journey to Chester could be completely stress-free or it could go on forever. We've compiled some handy travel tips that will help you start your next great escape on the right foot. What to pack in your hand luggage:

  • First and foremost, pack in your passport, travel docs, credit cards and medications. Next, you'll need some in-flight entertainment to while away the hours. A juicy novel and a tablet crammed with your favourite shows are some fantastic options. If you hope to take a quick snooze, a quality neck pillow and a pair of earplugs will also be useful. Finally, make room for a toothbrush and some facial wipes to ensure you step off the plane looking fresh and ready to go.

Do not pack the following items in your hand luggage:

  • While the list of restricted items differs between airlines, the general rule to follow is avoid carrying anything sharp, flammable or explosive. This includes things like tools, metal cutlery, spray paint and fireworks. Sporting equipment like ice skates, and items that could injure passengers, such as swords and guns, can't come on board with you either.

What to wear on a flight:

  • Go for comfort over style. Prepare for changes in temperature by dressing in layers, and opt for slightly roomy, flat shoes like sneakers.
  • Deep vein thrombosis (DVT), a blood clot condition caused by lengthy periods of inactivity, can be a risk on long-haul flights. Try to wander around the cabin or do some simple exercises in your seat to improve your circulation.

How to get through airport security fast when flying to Chester?
It's all about being organised. We've compiled some useful tips for a hassle-free trip through security. Look out Chester, here you come:

  • Security personnel first need to determine that you have a valid passport and matching boarding pass before you can proceed any further. Keep them within easy reach.
  • After that, both you and your carry-on bag will be X-rayed. To speed things up, remove anything that is likely to set the alarm off. Personal belongings like your jacket, belt and headphones will be required to go through the machine.
  • For just a few minutes, you'll have to unplug from technology. Your phone, laptop and any other electronic gadgets also need to go through the scanner.
  • Travelling with a new perfume? As long as the volume is no larger than 3.4 ounces (100 millilitres) and it's stored in a clear zip-lock bag, you can keep it with you in your carry-on luggage.
  • Slip-on shoes are a great footwear choice as you're less likely to be required to remove them when going through security. Safety boots and other bulky shoes are often subjected to extra screening.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, put them in your checked suitcase. They won't be allowed in the cabin.

Flights to Chester information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Destination city name
Newburgh
Return price
€153
*Available to Expedia members.