Flights To Chester - Cheap Flights Starting at CA $100

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

Jet to one of Chester's top cities

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.

Sat, Oct 3 - Sat, Oct 3
YHM
John C. Munro Hamilton Intl.
YHZ
Stanfield Intl.
CA $181 Roundtrip, found 2 days ago
CA $181
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Sat, Oct 3 from John C. Munro Hamilton Intl. to Stanfield Intl., returning Sat, Oct 3, priced at CA $181 found 2 days ago
Thu, Sep 10 - Sun, Sep 13
YKF
Region of Waterloo Intl.
YHZ
Stanfield Intl.
CA $198 Roundtrip, found 1 hour ago
CA $198
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Thu, Sep 10 from Region of Waterloo Intl. to Stanfield Intl., returning Sun, Sep 13, priced at CA $198 found 1 hour ago
Fri, Oct 30 - Wed, Dec 2
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
CA $204 Roundtrip, found 9 hours ago
CA $204
Roundtrip
found 9 hours ago
Select Flair Airlines flight, departing Fri, Oct 30 from Pearson Intl. to Stanfield Intl., returning Wed, Dec 2, priced at CA $204 found 9 hours ago
Fri, Sep 18 - Sat, Sep 26
YTZ
Billy Bishop Toronto City
YHZ
Stanfield Intl.
CA $238 Roundtrip, just found
CA $238
Roundtrip
just found
Select Porter Airlines flight, departing Fri, Sep 18 from Billy Bishop Toronto City to Stanfield Intl., returning Sat, Sep 26, priced at CA $238 just found
Wed, Sep 2 - Wed, Sep 9
YYZ
Pearson Intl.
YSJ
Saint John
CA $296 Roundtrip, found 6 hours ago
CA $296
Roundtrip
found 6 hours ago
Select Flair Airlines flight, departing Wed, Sep 2 from Pearson Intl. to Saint John, returning Wed, Sep 9, priced at CA $296 found 6 hours ago
Sun, Sep 20 - Sun, Sep 20
YUL
Pierre Elliott Trudeau Intl.
YHZ
Stanfield Intl.
CA $328 Roundtrip, found 4 hours ago
CA $328
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Sun, Sep 20 from Pierre Elliott Trudeau Intl. to Stanfield Intl., returning Sun, Sep 20, priced at CA $328 found 4 hours ago
Sat, Oct 10 - Fri, Oct 16
YHU
Montreal Metropolitan Airport
YHZ
Stanfield Intl.
CA $354 Roundtrip, found 2 hours ago
CA $354
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Sat, Oct 10 from Montreal Metropolitan Airport to Stanfield Intl., returning Fri, Oct 16, priced at CA $354 found 2 hours ago
Fri, Oct 2 - Fri, Oct 2
YYC
Calgary Intl.
YHZ
Stanfield Intl.
CA $373 Roundtrip, found 1 day ago
CA $373
Roundtrip
found 1 day ago
Select WestJet flight, departing Fri, Oct 2 from Calgary Intl. to Stanfield Intl., returning Fri, Oct 2, priced at CA $373 found 1 day ago
OriginDestinationTravel datesFlights from*
YKFGoffsSeptember 10 to September 13CA $198
YYZGoffsNovember 29 to December 2CA $215
YYZSaint JohnSeptember 9 to September 21CA $296
YYZSaint JohnSeptember 9 to September 21CA $296
YOWGoffsSeptember 29 to September 29CA $381
YEGGoffsOctober 30 to November 3CA $387
YYCGoffsSeptember 24 to October 1CA $396
MCOGoffsSeptember 17 to September 24CA $525
TPAGoffsSeptember 29 to October 20CA $566
YOWSaint JohnSeptember 14 to September 15CA $571
YYCSaint JohnOctober 9 to October 19CA $597
YEGSaint JohnSeptember 16 to September 21CA $638
YVRSaint JohnOctober 16 to October 22CA $658
YYTSaint JohnNovember 5 to November 12CA $1,142
PEKGoffsNovember 18 to November 22CA $1,795
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YKFGoffsAugust 29 to September 10CA $299
MCOGoffsAugust 29 to September 8CA $540
YYZSaint JohnAugust 29 to August 31CA $611
YYZSaint JohnAugust 29 to August 31CA $611
YYZGoffsAugust 29 to September 1CA $623
YXXGoffsAugust 30 to October 23CA $655
YYCGoffsAugust 28 to September 11CA $714
YOWGoffsAugust 29 to September 3CA $803
YYCSaint JohnAugust 29 to September 5CA $890
YYTGoffsAugust 28 to September 4CA $891
YEGGoffsAugust 28 to September 1CA $978
YVRSaint JohnAugust 29 to September 1CA $1,027
YEGSaint JohnAugust 29 to August 31CA $1,050
YYTSaint JohnAugust 29 to September 5CA $1,541
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Coastal Inn Halifax
3.0-star property

Coastal Inn Halifax

Sep 18 - Sep 25

7 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop • Coach

Halifax (YHZ) to Hamilton (YHM)

Air Canada • Non-stop • Coach
Price was CA $1,577, price is now CA $1,136 per person
CA $1,136
per person
found 1 day ago
Sandman Signature Dartmouth Hotel & Suites
3.0-star property

Sandman Signature Dartmouth Hotel & Suites

Sep 18 - Sep 25

7 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop • Coach

Halifax (YHZ) to Hamilton (YHM)

Air Canada • Non-stop • Coach
Price was CA $2,143, price is now CA $1,502 per person
CA $1,502
per person
found 1 day ago
Residence Inn by Marriott Halifax Downtown
3.0-star property

Residence Inn by Marriott Halifax Downtown

Sep 19 - Sep 26

7 night stay

Montreal (YMQ) to Halifax (YHZ)

Porter Airlines • Roundtrip • Coach
Price was CA $3,281, price is now CA $2,402 per person
CA $2,402
per person
found 3 hours ago
Don't see what you're looking for?
See all available trips from Hamilton 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 Tancook Island are located nearby.
8.2/10 Very good! (558 reviews)
"The breakfast at this place is paid although Expedia said it's free."

Reviewed on Aug 25, 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! (43 reviews)
"Right on the water, multiple decks to enjoy the view and sit or lay back. Comfortable cottage, felt homey and had everything you would need. Full working kitchen with dishes, medium sized fridge, great updated shower- so nice! Comfortable bed and slept like a baby! Quiet and tranquil!"

Reviewed on Aug 25, 2026

Opens in a new windowOceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
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.
Opens in a new windowFuture Inns Halifax
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 Halifax Citadel are located nearby.
8.6/10 Excellent! (1,021 reviews)
"What we liked during our stay is the convenience. Breakfast was provided but with only few options, only in large quantities. The sink in the washroom needed more cleaning though. But so far, we had a good stay for a night."

Reviewed on Aug 25, 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 $181 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, October 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 $181 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 $181 and CA $1,795. 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.