Flights To Chester - Cheap Flights Starting at CA $100

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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.

Fri, Nov 27 - Tue, Dec 1
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
CA $193 Roundtrip, just found
CA $193
Roundtrip
just found
Select Flair Airlines flight, departing Fri, Nov 27 from Pearson Intl. to Stanfield Intl., returning Tue, Dec 1, priced at CA $193 just found
Fri, Oct 16 - Mon, Oct 19
YYZ
Pearson Intl.
YSJ
Saint John
CA $270 Roundtrip, found 2 days ago
CA $270
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Fri, Oct 16 from Pearson Intl. to Saint John, returning Mon, Oct 19, priced at CA $270 found 2 days ago
Thu, Oct 29 - Thu, Oct 29
YHM
John C. Munro Hamilton Intl.
YHZ
Stanfield Intl.
CA $271 Roundtrip, found 2 days ago
CA $271
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Thu, Oct 29 from John C. Munro Hamilton Intl. to Stanfield Intl., returning Thu, Oct 29, priced at CA $271 found 2 days ago
Thu, Nov 26 - Wed, Dec 2
YTZ
Billy Bishop Toronto City
YHZ
Stanfield Intl.
CA $321 Roundtrip, just found
CA $321
Roundtrip
just found
Select Air Transat flight, departing Thu, Nov 26 from Billy Bishop Toronto City to Stanfield Intl., returning Wed, Dec 2, priced at CA $321 just found
Tue, Dec 1 - Tue, Dec 1
YYT
St. John's Intl.
YHZ
Stanfield Intl.
CA $346 Roundtrip, found 2 days ago
CA $346
Roundtrip
found 2 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 2 days ago
Tue, Nov 10 - Tue, Nov 10
YEG
Edmonton Intl.
YHZ
Stanfield Intl.
CA $362 Roundtrip, found 1 day ago
CA $362
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Tue, Nov 10 from Edmonton Intl. to Stanfield Intl., returning Tue, Nov 10, priced at CA $362 found 1 day ago
Wed, Nov 4 - Wed, Nov 11
YHU
Montreal Metropolitan Airport
YHZ
Stanfield Intl.
CA $397 Roundtrip, just found
CA $397
Roundtrip
just found
Select Air Transat flight, departing Wed, Nov 4 from Montreal Metropolitan Airport to Stanfield Intl., returning Wed, Nov 11, priced at CA $397 just found
Mon, Nov 2 - Sun, Nov 8
YUL
Pierre Elliott Trudeau Intl.
YHZ
Stanfield Intl.
CA $399 Roundtrip, just found
CA $399
Roundtrip
just found
Select Porter Airlines flight, departing Mon, Nov 2 from Pierre Elliott Trudeau Intl. to Stanfield Intl., returning Sun, Nov 8, priced at CA $399 just found
OriginDestinationTravel datesFlights from*
YYZGoffsJanuary 20 to January 26CA $187
YYZGoffsJanuary 20 to January 26CA $187
YEGGoffsNovember 3 to November 5CA $366
YYCGoffsOctober 31 to November 5CA $408
YVRGoffsNovember 9 to November 16CA $424
YYTGoffsNovember 25 to November 27CA $468
YOWGoffsNovember 29 to November 29CA $524
TPAGoffsDecember 22 to January 7CA $561
MCOGoffsJanuary 8 to January 16CA $586
YYZSaint JohnNovember 11 to November 13CA $592
YKFSaint JohnNovember 11 to November 13CA $592
YYCSaint JohnOctober 30 to November 10CA $676
PEKGoffsNovember 18 to November 23CA $1,983
PEKSaint JohnNovember 7 to November 21CA $2,128
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YKFGoffsOctober 17 to October 24CA $191
YYZGoffsOctober 17 to October 24CA $288
YYZSaint JohnOctober 16 to October 23CA $338
YYZSaint JohnOctober 16 to October 23CA $338
YYTGoffsOctober 17 to October 24CA $692
YVRGoffsOctober 17 to October 23CA $714
YOWGoffsOctober 16 to October 24CA $738
MCOGoffsOctober 16 to October 24CA $764
YEGGoffsOctober 18 to October 23CA $849
YYCGoffsOctober 18 to October 22CA $904
TPAGoffsOctober 18 to November 3CA $916
YOWSaint JohnOctober 18 to October 23CA $931
YEGSaint JohnOctober 16 to October 19CA $1,021
YVRSaint JohnOctober 16 to October 18CA $1,112
PEKGoffsOctober 17 to October 30CA $2,023
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Mersey River Chalets a nature retreat
3.5-star property

Mersey River Chalets a nature retreat

Oct 20 - Oct 24

4 night stay

Toronto (YYZ) to Halifax (YHZ)

Flair Airlines • Roundtrip • Coach
Price was CA $707, price is now CA $583 per person
CA $583
per person
found 7 hours 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 25 - Dec 28

3 night stay

Toronto (YTO) to Halifax (YHZ)

Flair Airlines • Coach

Halifax (YHZ) to Toronto (YTO)

Porter Airlines • Coach
Save 100% on your flight
Price was CA $1,715, price is now CA $1,236 per person
CA $1,236
per person
found 1 day ago
Burgundy Dream Bed and Breakfast
2.0-star property

Burgundy Dream Bed and Breakfast

Oct 26 - Oct 30

4 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $987, price is now CA $838 per person
CA $838
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! (2,552 reviews)
"This is a nice hotel, clean and kept up to date. It's in a very convenient location. do not believe there is any sort of breakfast offered, however I was out the door by 6 am so cannot verify. The restaurant has one hell of a Chef - the food was simply outstanding. The restaurant looks like your ..."

Reviewed on Oct 10, 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 $187 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 $187 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 $187 and CA $2,128. 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.