Cheap Flights to Chester from $70 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Chester?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 4 - Sun, Dec 6
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Flair Airlines flight, departing Fri, Dec 4 from Pearson Intl. to Stanfield Intl., returning Sun, Dec 6, priced at $136 just found
Mon, Nov 9 - Sat, Nov 14
YHM
John C. Munro Hamilton Intl.
YHZ
Stanfield Intl.
$232 Roundtrip, found 10 hours ago
$232
Roundtrip
found 10 hours ago
Select Porter Airlines flight, departing Mon, Nov 9 from John C. Munro Hamilton Intl. to Stanfield Intl., returning Sat, Nov 14, priced at $232 found 10 hours ago
Fri, Oct 16 - Mon, Oct 19
YYZ
Pearson Intl.
YSJ
Saint John
$255 Roundtrip, found 4 hours ago
$255
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Fri, Oct 16 from Pearson Intl. to Saint John, returning Mon, Oct 19, priced at $255 found 4 hours ago
Thu, Nov 5 - Mon, Nov 9
YUL
Pierre Elliott Trudeau Intl.
YHZ
Stanfield Intl.
$288 Roundtrip, found 11 hours ago
$288
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Thu, Nov 5 from Pierre Elliott Trudeau Intl. to Stanfield Intl., returning Mon, Nov 9, priced at $288 found 11 hours ago
Tue, Oct 27 - Tue, Nov 3
YHM
John C. Munro Hamilton Intl.
YSJ
Saint John
$433 Roundtrip, found 8 hours ago
$433
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Tue, Oct 27 from John C. Munro Hamilton Intl. to Saint John, returning Tue, Nov 3, priced at $433 found 8 hours ago
Tue, Oct 27 - Sat, Oct 31
IAD
Washington Dulles Intl.
YHZ
Stanfield Intl.
$459 Roundtrip, just found
$459
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Oct 27 from Washington Dulles Intl. to Stanfield Intl., returning Sat, Oct 31, priced at $459 just found
Wed, Aug 25 - Wed, Sep 1
BOS
Logan Intl.
YHZ
Stanfield Intl.
$466 Roundtrip, found 3 days ago
$466
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Aug 25 from Logan Intl. to Stanfield Intl., returning Wed, Sep 1, priced at $466 found 3 days ago
Thu, Nov 19 - Fri, Nov 27
DFW
Dallas-Fort Worth Intl.
YHZ
Stanfield Intl.
$468 Roundtrip, found 3 hours ago
$468
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Nov 19 from Dallas-Fort Worth Intl. to Stanfield Intl., returning Fri, Nov 27, priced at $468 found 3 hours ago
OriginDestinationTravel DatesFlights From*
YKFGoffsOctober 29 to November 2$134
YYZGoffsNovember 8 to November 16$136
YEGGoffsNovember 20 to November 26$257
YYTGoffsNovember 19 to November 20$319
YYCGoffsNovember 18 to November 20$324
YVRGoffsNovember 18 to November 20$336
TPAGoffsJanuary 8 to January 17$359
YOWGoffsNovember 19 to November 22$405
YYZSaint JohnDecember 4 to December 5$433
YYZSaint JohnDecember 4 to December 5$433
MCOGoffsJanuary 14 to January 19$480
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
YYZGoffsOctober 16 to October 19$241
YYZGoffsOctober 16 to October 19$241
YYZSaint JohnOctober 16 to October 19$255
YYZSaint JohnOctober 16 to October 19$255
YYTGoffsOctober 16 to October 20$577
TPAGoffsOctober 16 to November 30$594
YVRGoffsOctober 17 to October 20$609
YYCGoffsOctober 18 to October 25$610
YEGGoffsOctober 16 to October 19$673
YOWGoffsOctober 16 to October 18$696
MCOGoffsOctober 17 to October 24$704
*Prices include taxes and fees

Best Chester Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Chateau Bedford, Trademark Collection by Wyndham
4.0-star property

Chateau Bedford, Trademark Collection by Wyndham

Dec 10 - Dec 15

5 night stay

Raleigh (RDU) to Halifax (YHZ)

United • Non-stop roundtrip • Coach
Price was $867, price is now $750 per person
$750
per person
found 1 day ago
The Lord Nelson Hotel & Suites
4.5-star property

The Lord Nelson Hotel & Suites

Dec 10 - Dec 15

5 night stay

Raleigh (RDU) to Halifax (YHZ)

United • Non-stop roundtrip • Coach
Price was $905, price is now $766 per person
$766
per person
found 1 day ago
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse
4.5-star property

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Dec 10 - Dec 15

5 night stay

Raleigh (RDU) to Halifax (YHZ)

United • Non-stop roundtrip • Coach
Price was $1,853, price is now $1,602 per person
$1,602
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Raleigh to Chester
View all trips

Travelers ❤️ These Chester 🏨

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
Book a stay at this business-friendly hotel in Western Shore. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Oak Island and Valverde Studio Gallery are located nearby.
8.4/10 Very Good! (623 reviews)
"Very clean and helpful staff I had a wonderful stay the aminties was above par. Will be looking forward to my next visit."

Reviewed on Oct 12, 2026

Opens in a new windowOak Island Resort & Conference Centre
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Chester NS
Book a stay at this beach cottage in East Chester. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Goat Lake and Graves Island Provincial Park are located nearby.
9.8/10 Exceptional! (49 reviews)
"This was a beautiful spot in Chester! The view is beautiful and serene, the cottage was lovely with all the comforts of homeYi is an excellent host!"

Reviewed on Oct 1, 2026

Opens in a new windowOceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Western Shore NS
Stay at this vacation home in Western Shore. Enjoy laundry facilities, an in-room coffeemaker, and a hot tub. Popular attractions Oak Island and Valverde Studio Gallery are located nearby.
Opens in a new windowLuxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Ocean front cottage in the heart of Hubbards.

Ocean front cottage in the heart of Hubbards.

Hubbards NS
Stay at this vacation home in Fox Point. Enjoy free WiFi, a garden, and patios. Popular attractions Shore Club Dance Hall and Black Harbour Distillers Inc. are located nearby.
9.8/10 Exceptional! (74 reviews)
"We loved the cottage and its convenient location for all our excursions on the south shore. It was cozy, clean and quiet. The mattress was really comfortable. We would definitely stay again."

Reviewed on Oct 12, 2026

Opens in a new windowOcean front cottage in the heart of Hubbards.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Chester?
During the last seven days, the cheapest roundtrip flight to Chester cost $134 on our site. Browse our unbeatable deals, make a booking and look forward to your next travel experience. This price was available on Travelocity for flights to Chester departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Chester?
According to Travelocity's direct return flight demand from January to December last year, December is the cheapest time to jump on a plane to Chester. Search for flights across this month and bag yourself an amazing bargain today.
How can I check my flight status to Chester?
Visit our helpful customer portal, Trips. You'll find everything related to your flight to Chester here, including helpful alerts about gate changes, flight status and more. Keep an eye out for Trips at the top right of the Travelocity homepage. Just sign up, log in and find the answers to your questions. Or you can access your itinerary while you're traveling and get real-time trip updates through the Travelocity app. All your itineraries are in one place, so you can easily share details with any members of your family flying with you.
How do I find the best deals on flights to Chester?
Being flexible with your travel dates is one way to nab an awesome deal. Travelocity makes it super simple to find your ideal fare through the "Flexible dates" function. First, search for your Chester flight, then compare prices for surrounding days by hitting the Flexible dates dropdown box above. Booking early and avoiding peak travel periods are other things you can do. In the last seven days, the cheapest price for a roundtrip flight to Chester was $134 on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Chester with Travelocity?
Start packing today and prepare for an unforgettable adventure with Travelocity. It's our goal to find you impressive deals on cheap flights to Chester. Whether you're looking for flexible airfares with plenty of wiggle room or cheap family flights from low-cost airlines, we've got you covered.
What are the most popular flight routes to Chester?
As a leading tourist destination, there are plenty of connections to Chester. Check out this list of popular routes:

  • Toronto, ON (YYZ-Pearson Intl.) to Stanfield Intl. Airport (YHZ) - 2,015 flights a month.
  • St. John's, NL (YYT-St. John's Intl.) to Stanfield Intl. Airport (YHZ) - 1,183 flights a month.
  • Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Stanfield Intl. Airport (YHZ) - 1,074 flights a month.

How much is a flight to Chester on average?
Based on prices found over the last seven days, roundtrip flights to Chester cost between $134 and $704. When you're ready to go, Travelocity will help you find a fare to suit your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Chester?
Where you depart from will typically determine how many hours your direct flight to Chester will be. Here are a handful of the popular routes to Chester and average flight times:

  • Toronto, ON (YYZ-Pearson Intl.) to Stanfield Intl. Airport (YHZ) - 2 hours and 1 minute
  • St. John's, NL (YYT-St. John's Intl.) to Stanfield Intl. Airport (YHZ) - 2 hours and 3 minutes
  • Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Stanfield Intl. Airport (YHZ) - 1 hour and 48 minutes

What can I expect on a flight to Chester?
Factors including which airline you're traveling with and where you're taking off from will largely determine your experience. Chances are you'll find all kinds of flights to Chester, from cheap flights for family vacations to business class journeys. Hot meals and entertainment are just a few examples of what most airlines provide on long-haul services.