Flights To Chester - Cheap Flights Starting at CA $147

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.

Thu, Nov 12 - Tue, Nov 17
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
CA $193 Roundtrip, found 1 hour ago
CA $193
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Thu, Nov 12 from Pearson Intl. to Stanfield Intl., returning Tue, Nov 17, priced at CA $193 found 1 hour ago
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, found 2 hours ago
CA $321
Roundtrip
found 2 hours ago
Select Air Transat 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
Tue, Nov 3 - Thu, Nov 5
YEG
Edmonton Intl.
YHZ
Stanfield Intl.
CA $366 Roundtrip, found 11 hours ago
CA $366
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Tue, Nov 3 from Edmonton Intl. to Stanfield Intl., returning Thu, Nov 5, priced at CA $366 found 11 hours ago
Sat, Oct 31 - Sun, Nov 1
YHU
Montreal Metropolitan Airport
YHZ
Stanfield Intl.
CA $397 Roundtrip, found 2 hours ago
CA $397
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Sat, Oct 31 from Montreal Metropolitan Airport to Stanfield Intl., returning Sun, Nov 1, priced at CA $397 found 2 hours ago
Thu, Oct 15 - Mon, Oct 19
YHU
Montreal Metropolitan Airport
YSJ
Saint John
CA $511 Roundtrip, found 3 days ago
CA $511
Roundtrip
found 3 days ago
Select Pascan Aviation flight, departing Thu, Oct 15 from Montreal Metropolitan Airport to Saint John, returning Mon, Oct 19, priced at CA $511 found 3 days ago
Sun, Nov 29 - Sun, Nov 29
YOW
Macdonald-Cartier Intl.
YHZ
Stanfield Intl.
CA $524 Roundtrip, found 11 hours ago
CA $524
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Sun, Nov 29 from Macdonald-Cartier Intl. to Stanfield Intl., returning Sun, Nov 29, priced at CA $524 found 11 hours ago
Tue, Dec 15 - Tue, Jan 5
YOW
Macdonald-Cartier Intl.
YSJ
Saint John
CA $658 Roundtrip, found 2 days ago
CA $658
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Dec 15 from Macdonald-Cartier Intl. to Saint John, returning Tue, Jan 5, priced at CA $658 found 2 days ago
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 2CA $408
YVRGoffsNovember 9 to November 16CA $424
YYTGoffsNovember 18 to November 23CA $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 13 to November 21CA $1,823
PEKSaint JohnNovember 7 to November 21CA $2,128
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YKFGoffsOctober 17 to October 24CA $191
YYZGoffsOctober 16 to October 19CA $278
YYZSaint JohnOctober 16 to October 23CA $338
YYZSaint JohnOctober 16 to October 23CA $338
YEGGoffsOctober 18 to November 21CA $607
YYTGoffsOctober 17 to October 24CA $692
YVRGoffsOctober 17 to October 23CA $714
MCOGoffsOctober 16 to October 24CA $764
YOWGoffsOctober 18 to October 24CA $799
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.
The Lord Nelson Hotel & Suites
4.5-star property

The Lord Nelson Hotel & Suites

Nov 20 - Nov 22

2 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $573, price is now CA $502 per person
CA $502
per person
found 1 day ago
The Lark & Loon Inn
3.5-star property

The Lark & Loon Inn

Oct 20 - Oct 24

4 night stay

Toronto (YYZ) to Halifax (YHZ)

Flair Airlines • Roundtrip • Coach
Price was CA $854, price is now CA $754 per person
CA $754
per person
found 13 hours ago
Chateau Bedford, Trademark Collection by Wyndham
4.0-star property

Chateau Bedford, Trademark Collection by Wyndham

Nov 20 - Nov 22

2 night stay

Hamilton (YHM) to Halifax (YHZ)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $599, price is now CA $530 per person
CA $530
per person
found 1 day 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 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,
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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.