Flights To Chester - Cheap Flights Starting at CA $93

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A large, two-story house with a steeply pitched roof and a chimney.

Chester

Flights
Chester
A white and red lighthouse with a clear blue sky in the background.

Western Shore

Flights
Western Shore

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.

Mon, Nov 30 - Fri, Dec 4
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
CA $193 Roundtrip, found 3 hours ago
CA $193
Roundtrip
found 3 hours ago
Select Flair Airlines flight, departing Mon, Nov 30 from Pearson Intl. to Stanfield Intl., returning Fri, Dec 4, priced at CA $193 found 3 hours ago
Mon, Nov 30 - Fri, Dec 4
YKF
Region of Waterloo Intl.
YHZ
Stanfield Intl.
CA $213 Roundtrip, found 6 hours ago
CA $213
Roundtrip
found 6 hours ago
Select Flair Airlines flight, departing Mon, Nov 30 from Region of Waterloo Intl. to Stanfield Intl., returning Fri, Dec 4, priced at CA $213 found 6 hours ago
Tue, Oct 20 - Tue, Oct 20
YHM
John C. Munro Hamilton Intl.
YHZ
Stanfield Intl.
CA $289 Roundtrip, found 5 days ago
CA $289
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Tue, Oct 20 from John C. Munro Hamilton Intl. to Stanfield Intl., returning Tue, Oct 20, priced at CA $289 found 5 days ago
Thu, Nov 26 - Wed, Dec 2
YTZ
Billy Bishop Toronto City
YHZ
Stanfield Intl.
CA $321 Roundtrip, found 2 hours ago
CA $321
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Thu, Nov 26 from Billy Bishop Toronto City to Stanfield Intl., returning Wed, Dec 2, priced at CA $321 found 2 hours ago
Mon, Oct 19 - Fri, Oct 23
YYZ
Pearson Intl.
YSJ
Saint John
CA $328 Roundtrip, found 14 hours ago
CA $328
Roundtrip
found 14 hours ago
Select Flair Airlines flight, departing Mon, Oct 19 from Pearson Intl. to Saint John, returning Fri, Oct 23, priced at CA $328 found 14 hours ago
Tue, Dec 1 - Tue, Dec 1
YYT
St. John's Intl.
YHZ
Stanfield Intl.
CA $346 Roundtrip, found 3 days ago
CA $346
Roundtrip
found 3 days ago
Select Air Canada flight, departing Tue, Dec 1 from St. John's Intl. to Stanfield Intl., returning Tue, Dec 1, priced at CA $346 found 3 days ago
Fri, Nov 20 - Sun, Nov 22
YEG
Edmonton Intl.
YHZ
Stanfield Intl.
CA $366 Roundtrip, found 6 hours ago
CA $366
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Fri, Nov 20 from Edmonton Intl. to Stanfield Intl., returning Sun, Nov 22, priced at CA $366 found 6 hours ago
Fri, Nov 13 - Mon, Nov 16
YHU
Montreal Metropolitan Airport
YHZ
Stanfield Intl.
CA $397 Roundtrip, found 5 hours ago
CA $397
Roundtrip
found 5 hours ago
Select Air Transat flight, departing Fri, Nov 13 from Montreal Metropolitan Airport to Stanfield Intl., returning Mon, Nov 16, priced at CA $397 found 5 hours ago
Sat, Nov 14 - Tue, Nov 17
YUL
Pierre Elliott Trudeau Intl.
YHZ
Stanfield Intl.
CA $399 Roundtrip, found 6 hours ago
CA $399
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Sat, Nov 14 from Pierre Elliott Trudeau Intl. to Stanfield Intl., returning Tue, Nov 17, priced at CA $399 found 6 hours ago
OriginDestinationTravel datesFlights from*
YKFGoffsNovember 13 to November 16CA $191
YYZGoffsNovember 20 to December 3CA $193
YEGGoffsNovember 3 to November 5CA $366
YYCGoffsNovember 1 to November 5CA $408
YVRGoffsNovember 9 to November 16CA $424
YYTGoffsNovember 18 to November 23CA $468
YOWGoffsNovember 29 to November 29CA $524
TPAGoffsJanuary 15 to January 24CA $551
MCOGoffsJanuary 8 to January 16CA $586
YKFSaint JohnNovember 11 to November 13CA $592
YYZSaint JohnNovember 11 to November 13CA $592
YYCSaint JohnOctober 30 to November 10CA $676
PEKGoffsNovember 13 to November 21CA $1,984
PEKSaint JohnNovember 7 to November 21CA $2,129
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YKFGoffsOctober 17 to October 24CA $191
YYZSaint JohnOctober 16 to October 19CA $484
YYZSaint JohnOctober 16 to October 19CA $484
YYZGoffsOctober 17 to October 23CA $517
YEGGoffsOctober 18 to November 21CA $607
YYTGoffsOctober 18 to October 24CA $761
MCOGoffsOctober 16 to October 24CA $765
YVRGoffsOctober 18 to October 23CA $785
YYCGoffsOctober 18 to October 28CA $807
YOWGoffsOctober 16 to October 21CA $811
TPAGoffsOctober 18 to November 3CA $916
YOWSaint JohnOctober 18 to October 23CA $931
YVRSaint JohnOctober 16 to October 18CA $1,112
YEGSaint JohnOctober 16 to October 19CA $1,129
PEKGoffsOctober 17 to October 30CA $2,023
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Burgundy Dream Bed and Breakfast
2.0-star property

Burgundy Dream Bed and Breakfast

Nov 7 - Nov 9

2 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $558, price is now CA $459 per person
CA $459
per person
found 1 day ago
Brewery Park Hotel
3.5-star property

Brewery Park Hotel

Dec 19 - Dec 22

3 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $1,192, price is now CA $980 per person
CA $980
per person
found 18 hours ago
Bridgetown Motor Inn
2.0-star property

Bridgetown Motor Inn

Oct 18 - Oct 23

5 night stay

Toronto (YTO) to Halifax (YHZ)

Flair Airlines • Roundtrip • Coach
Price was CA $782, price is now CA $658 per person
CA $658
per person
found 1 day ago
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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.
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,
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Future Inns Halifax

Future Inns Halifax

3 out of 5
30 Fairfax Dr Halifax NS
Book a stay at this business-friendly hotel in Halifax. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
9.2/10 Wonderful! (2,557 reviews)
"Hotel was clean and staff was friendly. The only complaint was the bed. It was dipped in the middle--due for replacement."

Reviewed on Oct 12, 2026

Opens in a new windowFuture Inns Halifax
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 CA $191 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, November 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 CA $191 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 CA $191 and CA $2,129. 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.