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$164+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — YYZ
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Wed 2/187:31 pm
ORF
-
YYZ
1 stop19h 22m
Multiple Airlines
Tue 2/243:40 pm
YYZ
-
ORF
1 stop26h 46m
Multiple Airlines
Deal found 2/4$300
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Wed 3/186:45 am
ORF
-
YYZ
2 stops16h 35m
Multiple Airlines
Wed 3/257:15 am
YYZ
-
ORF
1 stop14h 32m
Multiple Airlines
Deal found 2/1$303
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:41 pm
ORF
-
YUL
2 stops27h 57m
Multiple Airlines
Mon 4/208:00 am
YUL
-
ORF
1 stop11h 29m
Multiple Airlines
Deal found 2/2$309
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Wed 2/187:31 pm
ORF
-
YYZ
1 stop19h 22m
Multiple Airlines
Wed 2/253:40 pm
YYZ
-
ORF
1 stop26h 46m
Multiple Airlines
Deal found 2/4$318
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/148:41 pm
ORF
-
YUL
2 stops27h 57m
Multiple Airlines
Thu 4/166:45 am
YUL
-
ORF
1 stop12h 44m
Multiple Airlines
Deal found 2/2$319
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
Wed 3/186:45 am
ORF
-
YVR
2 stops31h 27m
Multiple Airlines
Wed 3/2511:00 pm
YVR
-
ORF
1 stop8h 15m
Multiple Airlines
Deal found 2/1$332
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Wed 2/187:31 pm
ORF
-
YYZ
1 stop19h 22m
Multiple Airlines
Fri 2/207:00 am
YYZ
-
ORF
1 stop11h 26m
Multiple Airlines
Deal found 2/4$332
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:41 pm
ORF
-
YYZ
2 stops17h 39m
Multiple Airlines
Thu 3/267:10 am
YYZ
-
ORF
1 stop14h 37m
Multiple Airlines
Deal found 2/2$335
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Wed 2/187:31 pm
ORF
-
YYZ
1 stop19h 22m
Multiple Airlines
Mon 2/233:40 pm
YYZ
-
ORF
2 stops20h 25m
Multiple Airlines
Deal found 2/4$340
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Mon 3/28:49 am
ORF
-
YUL
1 stop15h 41m
Multiple Airlines
Mon 3/98:00 am
YUL
-
ORF
1 stop10h 26m
Multiple Airlines
Deal found 2/4$341
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Thu 3/268:41 pm
ORF
-
YUL
1 stop28h 04m
Multiple Airlines
Mon 3/308:00 am
YUL
-
ORF
1 stop11h 46m
Multiple Airlines
Deal found 2/4$347
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Wed 2/187:31 pm
ORF
-
YYZ
1 stop19h 22m
Multiple Airlines
Thu 2/262:20 pm
YYZ
-
ORF
1 stop8h 06m
Multiple Airlines
Deal found 2/4$348

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$300
(Kiwi.com)

One-way from

$164
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$374
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, 7% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 4, 2026.
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

Wed 2/18

7:31 pm-2:53 pm

1 stop19h 22m

Toronto Pearson Intl

Mon 2/23

3:40 pm-6:26 pm

1 stop26h 46m

$300

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 3/18

6:45 am-12:14 am

1 stop17h 29m

Toronto Pearson Intl

Wed 3/25

7:15 am-9:47 pm

1 stop14h 32m

$304

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Tue 4/14

8:41 pm-12:38 am

2 stops27h 57m

Montreal Pierre Elliott Trudeau Intl

Thu 4/16

6:45 am-7:29 pm

1 stop12h 44m

$319

NorfolkVancouver

ORF - YVR

ORFYVR

Norfolk

Wed 3/18

6:45 am-11:12 am

2 stops31h 27m

Vancouver Intl

Wed 3/25

11:00 pm-10:15 am

1 stop8h 15m

$332

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 2/18

7:31 pm-2:53 pm

1 stop19h 22m

Toronto Pearson Intl

Fri 2/20

7:00 am-6:26 pm

1 stop11h 26m

$332

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Tue 3/24

8:41 pm-2:20 pm

2 stops17h 39m

Toronto Pearson Intl

Thu 3/26

7:10 am-9:47 pm

1 stop14h 37m

$335

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Mon 3/2

8:49 am-12:30 am

1 stop15h 41m

Montreal Pierre Elliott Trudeau Intl

Mon 3/9

8:00 am-6:26 pm

1 stop10h 26m

$341

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 2/18

7:31 pm-2:53 pm

1 stop19h 22m

Toronto Pearson Intl

Thu 2/26

2:20 pm-10:26 pm

1 stop8h 06m

$348

NorfolkHalifax

ORF - YHZ

ORFYHZ

Norfolk

Mon 3/16

6:45 am-11:54 pm

2 stops16h 09m

Halifax Intl

Mon 3/23

7:00 am-9:47 pm

2 stops15h 47m

$361

NorfolkHalifax

ORF - YHZ

ORFYHZ

Norfolk

Sat 5/30

5:44 pm-11:32 pm

1 stop4h 48m

Halifax Intl

Wed 6/3

2:50 pm-7:22 pm

1 stop5h 32m

$371

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 49 results
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5

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.

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 February 4, 2026.
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
8,144 reviews

Overall

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

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
8,144 reviews
Delta
7.9
Good
8,144 reviews

Overall

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

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
9,236 reviews
Delta
7.9
Good
8,144 reviews

Overall

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

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
11,222 reviews
Delta
7.9
Good
8,144 reviews

Overall

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

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
3,255 reviews
Delta
7.9
Good
8,144 reviews

Overall

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

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
10,688 reviews
Delta
7.9
Good
8,144 reviews

Overall

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

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 4h 48m. United Airlines provides one of the quickest options available for as low as $371. The distance from Chesapeake to Canada is about 860 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 American Airlines, with whom users have recently found tickets for as low as $164. However, be on the lookout for offers from United Airlines and Delta, 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 - Vancouver Intl, Norfolk - Toronto Pearson 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.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$129Average$499FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$136Average$547FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$156Average$624FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$315Average$622FlexibilityNo cancel feeOn-time71%
WestJetCheapest$433Average$599FlexibilityNo cancel feeOn-time60%

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