Flights To Chester - Cheap Flights Starting at CA $102

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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.

Tue, Sep 15 - Tue, Sep 15
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
CA $203 Roundtrip, found 13 hours ago
CA $203
Roundtrip
found 13 hours ago
Select Porter Airlines flight, departing Tue, Sep 15 from Pearson Intl. to Stanfield Intl., returning Tue, Sep 15, priced at CA $203 found 13 hours ago
Thu, Sep 10 - Wed, Sep 16
YHM
John C. Munro Hamilton Intl.
YHZ
Stanfield Intl.
CA $210 Roundtrip, just found
CA $210
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Sep 10 from John C. Munro Hamilton Intl. to Stanfield Intl., returning Wed, Sep 16, priced at CA $210 just found
Tue, Jul 14 - Sat, Jul 25
YKF
Region of Waterloo Intl.
YHZ
Stanfield Intl.
CA $221 Roundtrip, found 2 hours ago
CA $221
Roundtrip
found 2 hours ago
Select Flair Airlines flight, departing Tue, Jul 14 from Region of Waterloo Intl. to Stanfield Intl., returning Sat, Jul 25, priced at CA $221 found 2 hours ago
Fri, Oct 2 - Fri, Oct 9
YYZ
Pearson Intl.
YSJ
Saint John
CA $222 Roundtrip, found 4 hours ago
CA $222
Roundtrip
found 4 hours ago
Select Flair Airlines flight, departing Fri, Oct 2 from Pearson Intl. to Saint John, returning Fri, Oct 9, priced at CA $222 found 4 hours ago
Thu, Sep 17 - Mon, Sep 21
YTZ
Billy Bishop Toronto City
YHZ
Stanfield Intl.
CA $230 Roundtrip, found 3 hours ago
CA $230
Roundtrip
found 3 hours ago
Select Porter Airlines flight, departing Thu, Sep 17 from Billy Bishop Toronto City to Stanfield Intl., returning Mon, Sep 21, priced at CA $230 found 3 hours ago
Mon, Aug 24 - Fri, Aug 28
YWG
Winnipeg James Armstrong Richardson Intl.
YHZ
Stanfield Intl.
CA $300 Roundtrip, found 2 hours ago
CA $300
Roundtrip
found 2 hours ago
Select WestJet flight, departing Mon, Aug 24 from Winnipeg James Armstrong Richardson Intl. to Stanfield Intl., returning Fri, Aug 28, priced at CA $300 found 2 hours ago
Fri, Oct 2 - Fri, Oct 2
YUL
Pierre Elliott Trudeau Intl.
YHZ
Stanfield Intl.
CA $374 Roundtrip, found 6 days ago
CA $374
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Fri, Oct 2 from Pierre Elliott Trudeau Intl. to Stanfield Intl., returning Fri, Oct 2, priced at CA $374 found 6 days ago
Mon, Aug 24 - Thu, Aug 27
YHU
Montreal Metropolitan Airport
YHZ
Stanfield Intl.
CA $388 Roundtrip, found 1 hour ago
CA $388
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Mon, Aug 24 from Montreal Metropolitan Airport to Stanfield Intl., returning Thu, Aug 27, priced at CA $388 found 1 hour ago
OriginDestinationTravel datesFlights from*
YYZGoffsSeptember 9 to September 16CA $204
YYZSaint JohnOctober 2 to October 9CA $222
YYZSaint JohnOctober 2 to October 9CA $222
YOWGoffsSeptember 10 to September 15CA $389
YYCGoffsAugust 4 to August 7CA $405
YEGGoffsAugust 21 to August 25CA $431
YYTGoffsOctober 7 to October 8CA $468
YVRGoffsAugust 20 to August 26CA $473
MCOGoffsAugust 18 to August 25CA $527
TPAGoffsAugust 28 to August 30CA $619
YVRSaint JohnAugust 29 to August 30CA $732
YEGSaint JohnOctober 15 to October 20CA $835
YYCSaint JohnSeptember 10 to September 17CA $876
YYTSaint JohnAugust 6 to August 13CA $990
YOWSaint JohnSeptember 16 to September 24CA $1,156
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YKFGoffsJuly 19 to July 28CA $273
YYZGoffsJuly 19 to July 24CA $326
YYZSaint JohnJuly 17 to July 20CA $444
YYZSaint JohnJuly 17 to July 20CA $444
YOWGoffsJuly 17 to August 9CA $623
YYCGoffsJuly 18 to July 22CA $626
YYTGoffsJuly 18 to August 17CA $694
MCOGoffsJuly 19 to July 23CA $697
TPAGoffsJuly 17 to July 21CA $726
YVRGoffsJuly 17 to July 19CA $828
YEGGoffsJuly 18 to July 21CA $855
YEGSaint JohnJuly 19 to July 23CA $1,086
YYCSaint JohnJuly 19 to August 2CA $1,169
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn
2.5-star property

South West Mermaid Inn

Sep 11 - Sep 18

7 night stay

Toronto (YYZ) to Halifax (YHZ)

WestJet • Roundtrip • Coach
Price was CA $1,004, price is now CA $813 per person
CA $813
per person
found 1 day ago
Seacliff- Luxury Halifax Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse
4.5-star property

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

Aug 11 - Aug 14

3 night stay

Toronto (YYZ) to Halifax (YHZ)

Flair Airlines • Roundtrip • Coach
Price was CA $4,842, price is now CA $3,720 per person
CA $3,720
per person
found 1 day ago
Sandman Signature Dartmouth Hotel & Suites
3.0-star property

Sandman Signature Dartmouth Hotel & Suites

Aug 23 - Aug 26

3 night stay

Ottawa (YOW) to Halifax (YHZ)

Porter Airlines • Roundtrip • Coach
Price was CA $1,174, price is now CA $947 per person
CA $947
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 Tancook Island are located nearby.
8.2/10 Very good! (516 reviews)
"Our only issuee was in the entertainment longe with regard to strong creosote odor from fireplace(not in use).Cused dismfort re eyes/ nose . Might be time to convert to propane !"

Reviewed on Jul 10, 2026

Opens in a new windowOak Island Resort & Conference Centre
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 breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Dartmouth Crossing are located nearby.
9.2/10 Wonderful! (2,267 reviews)
"We stay at this location often when in Halifax and have always been very happy with it."

Reviewed on Jul 10, 2026

Opens in a new windowFuture Inns Halifax
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
133 Kearney Lake Rd Halifax NS
Book a stay at this business-friendly hotel in Halifax. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dartmouth Crossing and Halifax Waterfront Boardwalk are located nearby.
9.2/10 Wonderful! (2,195 reviews)
"The hotel was executional. The bed was so comfortable, Very clean, very organized. I loved how for breakfast they had someone service you.and she is very friendly. Unfortunately I did not get her name. Would have loved to mention her."

Reviewed on Jul 10, 2026

Opens in a new windowChateau Bedford, Trademark Collection by Wyndham
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Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
98 Chain Lake Dr Halifax NS
Book a stay at this family-friendly hotel in Beechville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Chocolate Lake Beach are located nearby.
8.6/10 Excellent! (1,010 reviews)
"Belle grande chambre bien équipée avec micro-ondes, frigo avec congélateur séparé d’une belle grandeur."

Reviewed on Jul 7, 2026

Opens in a new windowCoastal Inn 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 $203 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, September 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 $203 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 $203 and CA $1,169. 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.