$75 Cheap flights to Chester

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Cheap flights to Chester from $75 One Way, $144 Round Trip

$144 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.

Fri, Dec 4 - Wed, Dec 9
YYZ
Toronto
YHZ
Halifax
$144 Roundtrip, found 7 hours ago
$144
Roundtrip
found 7 hours ago
Select Flair Airlines flight, departing Fri, Dec 4 from Toronto to Halifax, returning Wed, Dec 9, priced at $144 found 7 hours ago
Fri, Oct 2 - Fri, Oct 9
YYZ
Toronto
YSJ
Saint John
$166 Roundtrip, found 4 days ago
$166
Roundtrip
found 4 days ago
Select Flair Airlines flight, departing Fri, Oct 2 from Toronto to Saint John, returning Fri, Oct 9, priced at $166 found 4 days ago
Thu, Oct 15 - Sun, Oct 18
YUL
Montreal
YHZ
Halifax
$261 Roundtrip, found 19 hours ago
$261
Roundtrip
found 19 hours ago
Select Porter Airlines flight, departing Thu, Oct 15 from Montreal to Halifax, returning Sun, Oct 18, priced at $261 found 19 hours ago
Wed, Sep 9 - Fri, Sep 18
LAX
Los Angeles
YHZ
Halifax
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Sep 9 from Los Angeles to Halifax, returning Fri, Sep 18, priced at $294 found 1 day ago
Wed, Sep 9 - Mon, Sep 14
BOS
Boston
YHZ
Halifax
$319 Roundtrip, found 2 days ago
$319
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Sep 9 from Boston to Halifax, returning Mon, Sep 14, priced at $319 found 2 days ago
Fri, Oct 9 - Tue, Oct 13
LGA
New York
YHZ
Halifax
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Oct 9 from New York to Halifax, returning Tue, Oct 13, priced at $367 found 2 days ago
Tue, Sep 22 - Wed, Sep 30
DCA
Washington
YHZ
Halifax
$369 Roundtrip, found 2 days ago
$369
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 22 from Washington to Halifax, returning Wed, Sep 30, priced at $369 found 2 days ago
Sat, Sep 19 - Sun, Sep 27
ORD
Chicago
YHZ
Halifax
$381 Roundtrip, found 2 days ago
$381
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 19 from Chicago to Halifax, returning Sun, Sep 27, priced at $381 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YYZGoffsAugust 9 to August 12$270
YYZGoffsAugust 9 to August 12$270
TPAGoffsAugust 8 to September 19$484
YOWGoffsAugust 9 to August 14$487
YYZSaint JohnAugust 7 to August 11$498
YYZSaint JohnAugust 7 to August 11$498
YYCGoffsAugust 8 to August 13$592
YVRGoffsAugust 8 to August 15$645
YEGGoffsAugust 7 to August 14$745
MCOGoffsAugust 7 to August 14$751
*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
$134 nightly
The price is $153 total per night from Sep 1 to Sep 2
$153 total
Sep 1 - Sep 2
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 Tancook ...
8.2/10 Very Good! (538 reviews)
"Beautiful spots, very clean, the restaurant was very accommodating. Amazing views."

Reviewed on Aug 2, 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
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $152 total per night from Sep 1 to Sep 2
$152 total
Sep 1 - Sep 2
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 ...
Opens in a new windowFuture Inns Halifax
Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
98 Chain Lake Dr Halifax NS
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $165 total per night from Sep 1 to Sep 2
$165 total
Sep 1 - Sep 2
Total with taxes and fees
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 ...
Opens in a new windowCoastal Inn Halifax
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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
$163 nightly
The price is $192 total per night from Aug 16 to Aug 17
$192 total
Aug 16 - Aug 17
Total with taxes and fees
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 ...
Opens in a new windowChateau Bedford, Trademark Collection by Wyndham
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

Orbitz is your one stop for guaranteed low prices on Chester flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Chester and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Chester Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Chester from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $144 and $751 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.