$75 Cheap flights to Chester

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Cheap flights to Chester from $75 One Way, $146 Round Trip

$146 return flights and $75 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 12 - Wed, Sep 16
YYZ
Toronto
YHZ
Halifax
$146 Roundtrip, found 2 hours ago
$146
Roundtrip
found 2 hours ago
Select Flair Airlines flight, departing Sat, Sep 12 from Toronto to Halifax, returning Wed, Sep 16, priced at $146 found 2 hours ago
Mon, Jun 22 - Mon, Jun 29
YYZ
Toronto
YSJ
Saint John
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Flair Airlines flight, departing Mon, Jun 22 from Toronto to Saint John, returning Mon, Jun 29, priced at $153 found 6 days ago
Thu, Oct 29 - Tue, Nov 10
BNA
Nashville
YHZ
Halifax
$290 Roundtrip, found 3 days ago
$290
Roundtrip
found 3 days ago
Select Air Canada flight, departing Thu, Oct 29 from Nashville to Halifax, returning Tue, Nov 10, priced at $290 found 3 days ago
Fri, Jul 3 - Wed, Jul 8
MCO
Orlando
YHZ
Halifax
$295 Roundtrip, found 5 hours ago
$295
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Jul 3 from Orlando to Halifax, returning Wed, Jul 8, priced at $295 found 5 hours ago
Sat, Oct 3 - Sat, Oct 17
BOS
Boston
YHZ
Halifax
$328 Roundtrip, found 2 days ago
$328
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 3 from Boston to Halifax, returning Sat, Oct 17, priced at $328 found 2 days ago
Sat, Aug 29 - Fri, Sep 4
FLL
Fort Lauderdale
YHZ
Halifax
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Sat, Aug 29 from Fort Lauderdale to Halifax, returning Fri, Sep 4, priced at $361 found 1 day ago
Wed, Sep 23 - Wed, Sep 30
ORD
Chicago
YHZ
Halifax
$384 Roundtrip, found 2 days ago
$384
Roundtrip
found 2 days ago
Select Air Canada flight, departing Wed, Sep 23 from Chicago to Halifax, returning Wed, Sep 30, priced at $384 found 2 days ago
Tue, Aug 25 - Tue, Sep 1
DCA
Washington
YHZ
Halifax
$429 Roundtrip, found 1 day ago
$429
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 25 from Washington to Halifax, returning Tue, Sep 1, priced at $429 found 1 day ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YKFGoffsJune 28 to June 30$162
YYZGoffsJune 27 to July 4$271
MCOGoffsJune 28 to July 2$391
YOWGoffsJune 28 to July 3$420
YYCGoffsJune 27 to July 1$436
YYTGoffsJune 27 to July 2$572
YVRGoffsJune 28 to July 2$586
YEGGoffsJune 26 to June 29$623
YTZSaint JohnJune 26 to June 30$817
TPAGoffsJune 26 to July 4$963
*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
The price is $143 total per night from Jul 9 to Jul 10
$143 total
per night
Jul 9 - Jul 10
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 ...
8.2/10 Very Good! (504 reviews)
"We love this hotel ! It was exceptional! The food was good and the place was kept so clean and lovely. Everything was so convenient! The pool was great and there was a washroom, a change room and a warm shower right near the pool! (Can’t say the same for the Alt airport hotel’s pool area!"

Reviewed on Jun 16, 2026

Opens in a new windowOak Island Resort & Conference Centre
"Luxurious Escapes Await: Private Hot Tubs and Kayaks at Norse Geodesic Retreat"

"Luxurious Escapes Await: Private Hot Tubs and Kayaks at Norse Geodesic Retreat"

Chester NS
The price is $248 total per night from Jul 20 to Jul 21
$248 total
per night
Jul 20 - Jul 21
Stay at this resort in Sherwood. Enjoy air conditioning. Popular attractions Sherwood Golf and Country Club and Shea Lake are located nearby.
10/10 Exceptional! (4 reviews)
"My partner and I booked for a little getaway for our anniversary, and i have nothing bad to say, a minor issue that was encountered was dealt with promptly, and overall it was a beautiful location and wonderful amenities for our needs."

Reviewed on Oct 18, 2025

Opens in a new window"Luxurious Escapes Await: Private Hot Tubs and Kayaks at Norse Geodesic Retreat"
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
133 Kearney Lake Rd Halifax NS
Fully refundableReserve now, pay when you stay
The price is $182 total per night from Jun 28 to Jun 29
$182 total
per night
Jun 28 - Jun 29
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 ...
9.2/10 Wonderful! (2,156 reviews)
"Very clean, hot breakfast, nice Hotel."

Reviewed on Jun 19, 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
The price is $152 total per night from Jun 21 to Jun 22
$152 total
per night
Jun 21 - Jun 22
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 ...
8.6/10 Excellent! (1,002 reviews)
"Breakfast didn't have very many options. But and over all great experience"

Reviewed on Jun 18, 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.

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

Why search for low cost fares on your flights to Chester when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Chester

Orbitz offers massive discounts and substantial last-minute savings on your Chester flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Chester flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Chester. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Chester but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Chester?
Book an airfare with one of the 16 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 $146 and $963 this week to Chester. Flying in from Toronto (YYZ)? The cheapest one-way prices started at just $75.
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.