Cheap Flights to Chester from $29

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How Much Does it Cost To Fly To Chester?

The cheapest prices found with in the last 7 days for return flights were $58 and $29 for one-way flights to Chester for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Mar 5 - Mon, Mar 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Mar 5 from Orlando Intl. to Bradley Intl., returning Mon, Mar 9, priced at $58 found 2 hours ago
OriginDestinationTravel DatesFlights From*
MCOWindsor LocksJanuary 31 to February 7$58
TPAWindsor LocksJanuary 26 to February 2$109
ATLWindsor LocksFebruary 28 to March 3$128
FLLWindsor LocksMarch 17 to March 23$137
ORDWindsor LocksJanuary 29 to February 7$158
SJUWindsor LocksMarch 10 to March 24$162
DENWindsor LocksFebruary 25 to March 4$168
DCAWindsor LocksJanuary 13 to January 21$173
CLTWindsor LocksJanuary 17 to January 22$175
LAXWindsor LocksFebruary 11 to February 25$230
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
TPAWindsor LocksJanuary 9 to January 12$144
MCOWindsor LocksJanuary 10 to January 14$154
ATLWindsor LocksJanuary 11 to January 15$219
SJUWindsor LocksJanuary 9 to January 12$219
FLLWindsor LocksJanuary 9 to January 12$232
DCAWindsor LocksJanuary 10 to January 20$274
CLTWindsor LocksJanuary 10 to January 31$299
LAXWindsor LocksJanuary 9 to January 14$310
DENWindsor LocksJanuary 9 to January 12$339
ORDWindsor LocksJanuary 11 to January 20$340
*Prices include taxes and fees

Chester Flight Information

Traveling to
Chester
Lowest Price
$58
Number of Airlines Serving
Airlines Serving
Frontier Airlines
Number of Daily Flights
Airlines with Direct Flights

Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Chester?
Spending some time inChester?There are 10airlinesthat jet intothis city.These are a few of the mostwell-known carriers:

  • American Airlines
  • Delta Air Lines
  • United Airlines

What airport is best to fly into Chester?
You'll find two airports servicing Chester. If you arrive at BDL, you'll be 30 mi from the city center. Another option is HFD, about 40 mi from the bright lights of the downtown area.
Where to stay in Chester
Choosing the ideal place to stay is a vital ingredient for a memorable travel experience. Select from 32 hotels in Chester and start planning the escape of your dreams!There's nothing more exciting than organizing your accommodations for your next trip. But after hours of comparing prices and amenities, it can get a little tedious. So why not take our advice and choose one of our recommended properties, like the Historic Huntington Home - Walk to Westfield River and the Two Bedroom house in the heart of the Berkshires?
Places to visit in Chester
Whether you simply want to admire it from the outside or inquire for information on building access, Chester Town Hall, a historic civic building, is a great addition to your itinerary. Want more? Take a walk and enjoy the unspoiled land at Becket Land Trust Historic Quarry. But that's not all there is. Lovers of the great outdoors will delight in a day trip to Glendale Falls.
How to get through airport security fast when traveling to Chester
These handy tips about airport security checks will save you a lot of time and energy on your journey to Chester:

  • Security personnel will expect to see your travel ID and boarding pass upon arrival. Have them in an accessible place, ready for inspection.
  • It's useful to know that belts with metal buckles can set off the body scanner's alarms. If you have one on, you may be instructed to step back and remove it before proceeding.
  • Laptops and other electronic devices must be placed in a bin to be X-rayed.
  • Traveling with your favorite cologne? As long as it's not bigger than 3.4 ounces (100 milliliters) and it's stored in a clear zip-lock bag, you can keep it in your hand luggage.
  • Give some thought to your choice of footwear. Slippers are awesome because they're super easy to slip out of when you're doing the airport security checks. Try wearing some on your next journey!
  • Put any pocketknives or other pointy metal items inside your checked luggage. Security personnel don't permit these in carry-on baggage.

Plane Tickets To Chester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chester. Browse through our inventory to explore a wide range of cheap flights to Chester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chester as you anxiously await to exit the plane and explore what Chester has to offer. Considering all the amazing local food and culture in Chester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chester today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.