$66 Cheap flights to Chester

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Cheap flights to Chester from $66 One Way, $130 Round Trip

$130 return flights and $66 one-way flights to Chester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 26 - Wed, Sep 30
YYZ
Toronto
YHZ
Halifax
$130 Roundtrip, found 1 hour ago
$130
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Sat, Sep 26 from Toronto to Halifax, returning Wed, Sep 30, priced at $130 found 1 hour ago
Sat, Oct 17 - Tue, Oct 20
YTZ
Toronto
YHZ
Halifax
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Sat, Oct 17 from Toronto to Halifax, returning Tue, Oct 20, priced at $167 found 2 days ago
Fri, Oct 2 - Mon, Oct 5
YYZ
Toronto
YSJ
Saint John
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Fri, Oct 2 from Toronto to Saint John, returning Mon, Oct 5, priced at $218 found 2 days ago
Thu, Oct 29 - Mon, Nov 2
FLL
Fort Lauderdale
YHZ
Halifax
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Thu, Oct 29 from Fort Lauderdale to Halifax, returning Mon, Nov 2, priced at $256 found 1 day ago
Wed, Oct 7 - Sat, Oct 10
DTW
Detroit
YHZ
Halifax
$263 Roundtrip, found 3 days ago
$263
Roundtrip
found 3 days ago
Select WestJet flight, departing Wed, Oct 7 from Detroit to Halifax, returning Sat, Oct 10, priced at $263 found 3 days ago
Wed, Jun 2 - Tue, Jun 8
BOS
Boston
YHZ
Halifax
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Wed, Jun 2 from Boston to Halifax, returning Tue, Jun 8, priced at $326 found 1 day ago
Thu, Oct 29 - Thu, Nov 5
EWR
New York
YHZ
Halifax
$372 Roundtrip, found 6 days ago
$372
Roundtrip
found 6 days ago
Select United flight, departing Thu, Oct 29 from New York to Halifax, returning Thu, Nov 5, priced at $372 found 6 days ago
Sat, Oct 10 - Tue, Oct 13
LGA
New York
YHZ
Halifax
$383 Roundtrip, found 20 hours ago
$383
Roundtrip
found 20 hours ago
Select Air Canada flight, departing Sat, Oct 10 from New York to Halifax, returning Tue, Oct 13, priced at $383 found 20 hours ago
Wed, Nov 11 - Mon, Nov 16
DCA
Washington
YHZ
Halifax
$396 Roundtrip, found 2 days ago
$396
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Nov 11 from Washington to Halifax, returning Mon, Nov 16, priced at $396 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YKFGoffsSeptember 18 to September 22$189
YYZGoffsSeptember 19 to September 24$237
YYZSaint JohnSeptember 18 to September 21$246
YYZSaint JohnSeptember 18 to September 21$246
YEGGoffsSeptember 20 to October 10$412
YYTGoffsSeptember 19 to September 26$441
YOWGoffsSeptember 20 to September 27$480
YVRGoffsSeptember 19 to September 26$497
YYCGoffsSeptember 18 to September 22$557
TPAGoffsSeptember 20 to September 25$632
YYCSaint JohnSeptember 19 to October 10$821
MCOGoffsSeptember 18 to September 20$992
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Chester Accommodation Deals

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
$195 nightly
The price is $222 total per night from Sep 20 to Sep 21
$222 total
Sep 20 - Sep 21
Total with taxes and fees
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 ...
Opens in a new windowOak Island Resort & Conference Centre
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Western Shore NS
$384 nightly
The price is $448 total per night from Sep 29 to Sep 30
$448 total
Sep 29 - Sep 30
Total with taxes and fees
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 ...
Opens in a new windowLuxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
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 ...
9.8/10 Exceptional! (46 reviews)
"We were extremely pleased when we drove down the lane to opening the door for the first time. It was a perfect location with lots of privacy and peacefulness. The cottage was well stocked with all the comforts of home. The owner responded within minutes of any questions.We made a great choice and ..."

Reviewed on Sep 14, 2026

Get rates
Opens in a new windowOceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
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Future Inns Halifax

Future Inns Halifax

3 out of 5
30 Fairfax Dr Halifax NS
$128 nightly
The price is $151 total per night from Oct 13 to Oct 14
$151 total
Oct 13 - Oct 14
Total with taxes and fees
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 ...
9.2/10 Wonderful! (2,484 reviews)
"Great place to stay been a few times now"

Reviewed on Sep 16, 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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Chester

Get the absolute lowest prices on flights to Chester by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Chester Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Chester flights.

Avoid Check-In Hassles When Traveling On Flights to Chester

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Chester flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Chester flight using Orbitz.

Frequently asked questions

Which airlines fly to Chester?
Book an airfare with one of the 18 airlines that operate services to Stanfield Intl. Airport (YHZ) and gear up for new adventures. This popular airport is a major entrance point for exploring Chester. When it's time to see this region, these trusted carriers will get you there:

  • Air Canada - 35 flights to Chester per month
  • American Airlines - 10 flights to Chester per month
  • WestJet - 9 flights to Chester per month

How much is a flight to Chester?
Travelers from near and far bagged round-trip deals ranging between $130 and $992 this week to Chester. Flying in from Toronto (YYZ)? The cheapest one-way prices started at just $66.
How to book the cheapest flight to Chester?
Snapping up cheap flights to Chester is as easy as booking with Orbitz. But if you'd love to make sure you're grabbing the best flight deals around, here are some suggestions to keep your wallet happy:

  • Depending on where you're departing from, select the 'Nearby airports' function (located under the departure and arrival form fields). In some instances, other departure points offer better value for money.
  • If your plans aren't written in stone, click on the 'Show flexible dates' option to compare flight deals for alternative departure dates. You may find an even better fare.
  • You can also use the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd like to fly.
  • If you've sorted your travel dates, don't waste time booking your flight. Prices usually get dearer as the departure date gets closer.
  • Make serious savings on your trip by bundling your flights, hotels and car rentals into an Orbitz package. Your credit card will thank you.
  • Whenever possible, avoid traveling in the most popular seasons. Airfares surge during summer, school breaks and around other vacation times like Easter, Thanksgiving and Christmas.

What is the best time to book a flight to Chester?
Book your tickets to Chester in January. This is the best month for low airfares, closely followed by February and August. Land cheap flights and make your dream vacation a reality with Orbitz.
What day of the week is the cheapest to book a flight to Chester?
If you're after inexpensive fares to Chester, the best days of the week to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a fabulous flight deal will be all yours.
What is the cheapest day of the week to fly to Chester?
According to Orbitz data from 2020, you ought to kick off your vacation on a Monday to score cheap flights to Chester. Next most affordable day? Tuesday. Saturday costs the most. So, leave early in the week if you'd like to score a low-priced fare and stretch your travel budget.
What is the cheapest month to fly to Chester?
To secure cheap flights to Chester, you should depart in August. If saving on your ticket is your main concern, Orbitz data shows that this is generally the best month to jet off. June is when airfares are at their peak.
Which airlines allow free cancellation?
When searching for your Chester flights on Orbitz, select "Filter by flexible change policies." This filter will show you all the airlines offering free cancellation and no change fees. Relax knowing that if things unexpectedly change, your flight can too.
What do I need for the flight to Chester?
From onboard entertainment to travel essentials like a pillow, there are several things a seasoned flyer always takes with them. To make sure you're organized for your adventure, check out this useful list:

  • Make sure you've got your travel papers and some identification. For international journeys, you'll need to take your passport. When purchasing your seats, always use the same details that are stated on your government-issued ID.
  • A well-packed carry-on bag is the key to a great flight experience. Given this journey to Chester is no short hop, take some snacks and things to keep you entertained. Something to read is sure to help pass the time.
  • Air conditioning and high altitudes can create a cool environment. No matter what the season is, carry an extra layer with you to keep warm and cozy on your plane trip.

How do I get cheap first-class/business deals to Chester?
If you think a business or first-class fare is way out of your reach, think again. Here are some tips to help you find a premium flight to Chester for a whole lot less:

  • Be more flexible with your travel dates and hold out for exclusive offers or sales on first or business-class airfares.
  • Search for a low-cost airline that offers seats in business class. They often come with more legroom and a glass of Champagne — but without the high price.
  • Take advantage of your airline's flight rewards program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

What is the best time to go to Chester?
Chester is an exciting getaway destination year-round, but the most popular months are January, March and April. If you're into warm weather, head there in the summertime. Like most places in the Northern Hemisphere, the summer season commences June 20. Temperatures normally range between 55 ºF and 70 ºF during the daytime.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.