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$99+ Cheap flights from Chesapeake, VA to Canada

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — YYZ
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Chesapeake to Canada

Cheapest flights from Chesapeake to Canada
Explore the most affordable flight options available from Chesapeake to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/233:11 pmORF - YYZ
1 stop20h 32mMultiple Airlines
Thu 1/17:10 amYYZ - ORF
1 stop11h 35mMultiple Airlines
Deal found 12/17$574
This United Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:30 amORF - YOW
1 stop10h 48mUnited Airlines
Fri 1/27:27 pmYOW - ORF
1 stop4h 14mUnited Airlines
Deal found 12/14$604
This Kiwi.com deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:11 pmORF - YUL
1 stop9h 19mMultiple Airlines
Sun 1/47:20 pmYUL - ORF
2 stops42h 46mMultiple Airlines
Deal found 12/15$631
This Kiwi.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/273:01 pmORF - YOW
1 stop8h 57mMultiple Airlines
Fri 1/29:30 amYOW - ORF
2 stops30h 57mMultiple Airlines
Deal found 12/14$681
This Kiwi.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:09 pmORF - YUL
1 stop9h 21mMultiple Airlines
Wed 12/313:55 pmYUL - ORF
1 stop7h 04mMultiple Airlines
Deal found 12/16$683
This Justfly.com deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:00 amORF - YYC
1 stop13h 09mWestJet
Sun 12/289:00 amYYC - ORF
2 stops25h 11mWestJet
Deal found 12/16$742
This American Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:01 amORF - YOW
2 stops10h 50mAmerican Airlines
Fri 1/26:45 amYOW - ORF
2 stops10h 30mAmerican Airlines
Deal found 12/14$806
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2810:07 amORF - YYZ
1 stop5h 23mAmerican Airlines
Tue 12/304:05 pmYYZ - ORF
1 stop3h 50mAmerican Airlines
Deal found 12/16$870
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:25 pmORF - YYZ
1 stop9h 34mAmerican Airlines
Thu 1/17:14 amYYZ - ORF
1 stop10h 01mAmerican Airlines
Deal found 12/17$901
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:30 amORF - YYZ
1 stop9h 32mUnited Airlines
Tue 12/303:30 pmYYZ - ORF
2 stops8h 11mUnited Airlines
Deal found 12/16$929
This FlightHub deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/235:23 amORF - YYZ
2 stops31h 00mWestJet
Thu 1/16:10 amYYZ - ORF
1 stop5h 07mWestJet
Deal found 12/17$996
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:30 amORF - YQB
2 stops16h 13mUnited Airlines
Sat 12/275:00 amYQB - ORF
2 stops18h 41mUnited Airlines
Deal found 12/16$996

Find flight deals from Chesapeake to Canada

Keep the following information in mind while searching for Chesapeake to Canada flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$233
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$720
Provider with most accurate pricing for Norfolk-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Toronto (YTO) flights.
Search Deals
From Chesapeake to Canada
Search Deals
One-way flight from Chesapeake to Canada
Search Deals
High demand for flights, 6% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Canada that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Chesapeake to Canada that are best for you.

Fly from

Chesapeake

Fly to

Canada

Route

Depart

Return

Price

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Thu 1/8

2:29 pm-12:11 am

1 stop9h 42m

Toronto Pearson Intl

Wed 1/14

3:40 pm-6:38 pm

1 stop26h 58m

$233

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Fri 1/9

6:45 am-2:05 pm

1 stop7h 20m

Toronto Pearson Intl

Mon 1/12

7:00 am-6:38 pm

1 stop11h 38m

$253

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Sat 1/31

8:00 am-8:11 pm

2 stops12h 11m

Toronto Pearson Intl

Sat 2/7

7:10 am-8:15 pm

1 stop13h 05m

$274

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 1/7

7:40 pm-8:11 pm

2 stops24h 31m

Toronto Pearson Intl

Wed 1/21

7:15 am-6:25 pm

1 stop11h 10m

$280

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Fri 1/30

6:45 am-2:16 pm

1 stop7h 31m

Toronto Pearson Intl

Fri 2/6

8:20 pm-8:15 pm

1 stop23h 55m

$281

NorfolkOttawa

ORF - YOW

ORFYOW

Norfolk

Fri 1/30

6:45 am-12:25 am

2 stops17h 40m

Ottawa

Fri 2/6

7:00 am-6:38 pm

1 stop11h 38m

$291

NorfolkHalifax

ORF - YHZ

ORFYHZ

Norfolk

Sat 1/31

6:45 am-5:31 pm

1 stop9h 46m

Halifax Intl

Sat 2/7

1:20 pm-6:38 pm

2 stops30h 18m

$308

NorfolkCalgary

ORF - YYC

ORFYYC

Norfolk

Thu 1/29

7:33 pm-9:02 pm

2 stops27h 29m

Calgary

Wed 2/4

12:15 am-6:38 pm

2 stops16h 23m

$314

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Thu 1/29

7:33 pm-12:43 am

3 stops29h 10m

Montreal Pierre Elliott Trudeau Intl

Thu 2/5

8:00 am-6:38 pm

1 stop10h 38m

$339

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Fri 4/24

6:05 am-12:14 am

1 stop18h 09m

Toronto Pearson Intl

Sun 4/26

8:00 pm-4:53 pm

1 stop20h 53m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 40 results
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Best time to book a flight from Chesapeake to Canada

Have a flexible travel schedule? Discover the best time to fly to Canada from Chesapeake with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Canada

What is the cheapest month to book a flight from Chesapeake to Canada?

Currently, June is the cheapest month in which you can book a flight from Chesapeake to Canada (average of $129). Flying from Chesapeake to Canada in December is currently the most expensive (average of $411). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from C6E to CA?

Find hourly flight availability from Chesapeake to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

When flying from Chesapeake to Canada, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 33% versus a flight in the morning.

What is the cheapest day to fly from Chesapeake to Canada?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Canada. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Canada flight should consider departing on Saturday mornings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Canada

Get insights into the airlines that provide service to Canada. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Canada. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chesapeake to Canada by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,005 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,092 reviews
Delta
7.9
Good
8,005 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,055 reviews
Delta
7.9
Good
8,005 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,204 reviews
Delta
7.9
Good
8,005 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,534 reviews
Delta
7.9
Good
8,005 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Canada. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chesapeake to Canada?

    A quick flight from Chesapeake to Canada can take about 7h 02m. United Airlines provides one of the quickest options available for as low as $363. The distance from Chesapeake to Canada is about 583 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chesapeake to Canada one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $134. However, be on the lookout for offers from American Airlines and WestJet, as they are both options that can get you from Chesapeake to Canada for a low price.

  • What are the most popular routes from Chesapeake to Canada?

    When deciding which route to take from Chesapeake to Canada consider Norfolk - Toronto Pearson Intl, Norfolk - Vancouver Intl or Norfolk - Calgary as they are the most popular.

  • Can I find deals for flights from Chesapeake to Canada that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Canada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Canada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Canada.

  • Can I find deals for business class flights from Chesapeake to Canada?

    Yes. Cheapflights offers flight deals from Chesapeake to Canada by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Canada?

    Currently, June is the cheapest month in which you can book a flight from Chesapeake to Canada (average of $129). Flying from Chesapeake to Canada in December is currently the most expensive (average of $411). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 5 airlines flying from Chesapeake to Canada

Discover the top 5 airlines that operate flights from Chesapeake to Canada. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$129Average$543FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$150Average$614FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$150Average$591FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$315Average$622FlexibilityNo cancel feeOn-time71%
WestJetCheapest$429Average$585FlexibilityNo cancel feeOn-time60%

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