$40 Cheap Flights to Chester, MA

View $40 flight on Mon, May 4, 2026Opens in a new window

Popular airlines to Chester

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How much is the cheapest flight to Chester?

Prices were available within the past 7 days and start at $40 for one-way flights and $89 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, May 1 - Mon, May 4
ATL
Atlanta
BDL
Hartford
$89 Roundtrip, just found
$89
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 1 from Atlanta to Hartford, returning Mon, May 4, priced at $89 just found
Breeze Airways
Fri, May 29 - Sat, May 30
MCO
Orlando
BDL
Hartford
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Breeze Airways flight, departing Fri, May 29 from Orlando to Hartford, returning Sat, May 30, priced at $110 just found
Delta
Thu, May 7 - Sun, May 10
ATL
Atlanta
BDL
Hartford
$159 Roundtrip, just found
$159
Roundtrip
just found
Select Delta flight, departing Thu, May 7 from Atlanta to Hartford, returning Sun, May 10, priced at $159 just found
United
Sat, May 2 - Mon, May 4
ATL
Atlanta
BDL
Hartford
$178 Roundtrip, just found
$178
Roundtrip
just found
Select United flight, departing Sat, May 2 from Atlanta to Hartford, returning Mon, May 4, priced at $178 just found
Southwest Airlines
Wed, May 13 - Tue, May 19
ATL
Atlanta
BDL
Hartford
$179 Roundtrip, found 2 hours ago
$179
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, May 13 from Atlanta to Hartford, returning Tue, May 19, priced at $179 found 2 hours ago

Alternative airports near Chester

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Bradley Intl. BDL. Cheapest option available. Average driving time to city center is 1 hour 1 minute. Flights from $309
BDL
Bradley Intl.
Cheapest
Average driving time to city center1 h 1 min
Flights from $309

Frequently asked questions

What month is the cheapest to fly to Chester?
Schedule your trip for May if you want to land a good price on your fare. It's the cheapest month to fly to Chester. If possible, avoid traveling during busy periods such as major public holidays or during big events.
Which US cities have the cheapest flights to Chester?
Washington, Chicago and Orlando generally offer cheap flights to Chester. Keep in mind that prices may vary based on factors such as holiday periods, number of stopovers and demand.
Which US cities fly direct to Chester?
There are 32 US destinations you're able to fly to Chester nonstop from. Explore the options by using the "Direct flights only" filter on Expedia and find the ideal departure point for you. Here are a few of the leading cities to head out from:

  • Washington
  • Chicago
  • Orlando
  • Atlanta
  • Charlotte

How to find a cheap flight to Chester?
To snag cheap flights to Chester, book as early as possible and travel during the low season. Want some insider advice? Fly on a Thursday and you'll save 16% on average compared to those who travel on a Sunday.* Set up price tracking on the Expedia app and we'll notify you the moment prices drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Chester?
It's possible to get awesome deals on last-minute departures to Chester, especially if your travel arrangements aren't set in stone. Consider flying from a different airport, changing your dates or selecting another airline to get a cheap flight to Chester.
How far in advance should I book a flight to Chester?
Get the travel dates you want and a fare that suits your budget by booking your domestic flight to Chester up to 28 days in advance. Search for tickets between two and four months ahead if you're visiting Chester from an international destination.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Chester?
Sundays are generally the best day to book a cheap flight to Chester, with savings of about 8% on average compared to Fridays. If you choose to purchase tickets on a Friday, expect to pay a higher price as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Chester?
A total of 10 carriers connect 34 airports all over the world to Chester. Here are a few of the major airlines to Chester, where Bradley Intl. Airport (BDL) is the major entry point:

  • Delta Air Lines
  • American Airlines
  • United Airlines
  • JetBlue Airways

Where do you fly into Chester?
Chester's main point of arrival is Bradley Intl. Airport (BDL). If you're looking for other nearby options when flying to Chester, check out Hartford, CT (HFD-Hartford - Brainard), Albany Intl. Airport (ALB) or Westfield, MA (BAF-Barnes Municipal). You can also opt to fly to Chester through Pittsfield, MA (PSF-Pittsfield Municipal).
How far is the airport from central Chester?
You'll be about 30 mi southeast of the center of Chester after arriving at Bradley Intl. Airport (BDL).
Can I save money by booking a Chester trip package?
Bundle your flight and hotel and you could save hundreds of dollars. What's more, you can add extras like activities and car rentals to your Chester flight and hotel package deal. With Expedia, it's a breeze to look after all your Chester travel plans in one place.
Can I change or cancel my flight to Chester?
It's often possible to cancel or change your flight to Chester. Many airlines let you cancel your ticket for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may offer you credit for future flights in place of a direct refund. To secure affordable flights to Chester with flexible change policies, select "No cancel fee" or "Changes included" during your search. Want more details? Visit our Customer Service Portal.

*Flight schedules are subject to change.

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Travel information

Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Destination city name
Hartford
Roundtrip price
$89

Trending flights to Chester

Prices were available within the past 7 days and start at $40 for one-way flights and $89 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Fri, May 1 - Mon, May 4
ATL
Atlanta
BDL
Hartford
$89 Roundtrip, just found
$89
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, May 1 from Atlanta to Hartford, returning Mon, May 4, priced at $89 just found

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