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Cheap flights from Canada to Chesapeake from C$ 244

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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — RIC
26 Apr — 3 May1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Chesapeake

Enter your travel dates to find the best prices.

Cheapest flights from Canada to Chesapeake
Explore the most affordable flight options available from Canada to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 27 March 2026.

Sat 16/52:40 p.m.
YOW
-
ORF
1 stop9h 10m
United Airlines
Sat 23/510:40 a.m.
ORF
-
YOW
1 stop13h 14m
United Airlines
Deal found 26/3C$ 398
Thu 30/45:50 p.m.
YOW
-
ORF
1 stop5h 42m
United Airlines
Fri 1/57:46 p.m.
ORF
-
YOW
1 stop14h 17m
United Airlines
Deal found 26/3C$ 403
Mon 20/47:30 p.m.
YOW
-
ORF
1 stop14h 01m
United Airlines
Wed 22/410:15 a.m.
ORF
-
YOW
1 stop6h 52m
United Airlines
Deal found 23/3C$ 405
Wed 3/63:27 p.m.
YEG
-
ORF
1 stop16h 40m
United Airlines
Sat 6/68:00 a.m.
ORF
-
YEG
1 stop9h 47m
United Airlines
Deal found 26/3C$ 430
Fri 29/58:45 a.m.
YWG
-
ORF
1 stop13h 45m
United Airlines
Tue 2/67:59 p.m.
ORF
-
YWG
2 stops16h 53m
United Airlines
Deal found 26/3C$ 433
Thu 23/48:00 p.m.
YYZ
-
ORF
2 stops38h 32m
Multiple Airlines
Thu 30/48:57 p.m.
ORF
-
YYZ
1 stop14h 48m
Multiple Airlines
Deal found 24/3C$ 479
Fri 24/77:30 p.m.
YOW
-
ORF
1 stop4h 14m
United Airlines
Fri 31/76:05 a.m.
ORF
-
YOW
1 stop3h 58m
United Airlines
Deal found 24/3C$ 480
Sun 17/55:05 a.m.
YOW
-
ORF
2 stops18h 45m
United Airlines
Sat 23/510:40 a.m.
ORF
-
YOW
1 stop13h 14m
United Airlines
Deal found 26/3C$ 490
Sat 2/53:35 p.m.
YVR
-
ORF
2 stops14h 56m
United Airlines
Tue 5/56:05 a.m.
ORF
-
YVR
1 stop10h 28m
United Airlines
Deal found 26/3C$ 495
Sat 31/1012:35 p.m.
YVR
-
ORF
1 stop7h 20m
United Airlines
Thu 5/118:00 a.m.
ORF
-
YVR
1 stop10h 49m
United Airlines
Deal found 24/3C$ 501
Fri 3/712:00 p.m.
YOW
-
ORF
2 stops12h 57m
United Airlines
Mon 13/76:00 a.m.
ORF
-
YOW
2 stops11h 10m
United Airlines
Deal found 26/3C$ 501
Fri 24/45:50 p.m.
YYZ
-
ORF
2 stops16h 42m
Multiple Airlines
Mon 27/48:57 p.m.
ORF
-
YYZ
1 stop17h 08m
Multiple Airlines
Deal found 25/3C$ 502

Find flight deals from Canada to Chesapeake

Keep the following information in mind while searching for Canada to Chesapeake flight deals. Data was last updated 27 March 2026.

Round-trip from

C$ 398

One-way from

C$ 244

Popular in

August

Cheapest in

December

Average price

C$ 494
United Airlines
  • United Airlines
  • 17/5-24/5
  • 2 total stops
  • 8h 18m total
  • Canada to Chesapeake
Search Deals
United Airlines
  • United Airlines
  • 7/5
  • 1 total stop
  • 9h 10m total
  • Canada to Chesapeake
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 180 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Canada to Chesapeake 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 629,999 searches. Data last updated 27 March 2026.
Use the filters below to find and compare flights from Canada to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Sun 17/5

7:30 p.m.-11:50 p.m.

1 stop4h 20m

Norfolk

Sun 24/5

6:05 a.m.-10:03 a.m.

1 stop3h 58m

C$ 398

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Sun 17/5

7:30 p.m.-9:31 a.m.

1 stop14h 01m

Norfolk

Sat 23/5

10:40 a.m.-11:54 p.m.

1 stop13h 14m

C$ 398

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Thu 30/4

5:50 p.m.-11:32 p.m.

1 stop5h 42m

Norfolk

Fri 1/5

7:46 p.m.-10:03 a.m.

1 stop14h 17m

C$ 403

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Fri 3/7

7:30 p.m.-9:34 a.m.

1 stop14h 04m

Norfolk

Mon 13/7

7:59 p.m.-11:54 p.m.

1 stop3h 55m

C$ 404

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Mon 20/4

10:44 a.m.-9:08 p.m.

1 stop10h 24m

Norfolk

Wed 22/4

10:15 a.m.-5:07 p.m.

1 stop6h 52m

C$ 405

EdmontonNorfolk

YEG - ORF

YEGORF

Edmonton

Wed 3/6

8:05 a.m.-11:44 p.m.

2 stops13h 39m

Norfolk

Sat 6/6

8:00 a.m.-3:47 p.m.

1 stop9h 47m

C$ 430

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 29/5

8:45 a.m.-11:30 p.m.

1 stop13h 45m

Norfolk

Tue 2/6

7:59 p.m.-11:52 a.m.

2 stops16h 53m

C$ 433

VancouverNorfolk

YVR - ORF

YVRORF

Vancouver Intl

Sat 2/5

3:35 p.m.-9:31 a.m.

2 stops14h 56m

Norfolk

Tue 5/5

6:05 a.m.-1:33 p.m.

1 stop10h 28m

C$ 495

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Tue 28/4

5:30 a.m.-7:00 p.m.

2 stops12h 30m

Norfolk

Thu 30/4

6:00 a.m.-11:52 a.m.

1 stop6h 52m

C$ 522

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Tue 28/4

6:15 a.m.-10:55 p.m.

2 stops15h 40m

Norfolk

Thu 30/4

5:45 a.m.-12:55 a.m.

2 stops20h 10m

C$ 560

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/3

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Canada to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Canada 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 Canada to Chesapeake

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

Currently, April is the cheapest month in which you can book a flight from Canada to Chesapeake (average of C$ 253). Flying from Canada to Chesapeake in November is currently the most expensive (average of C$ 540). 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 Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated 27 March 2026.
See what other customers who have flown with United Airlines,WestJet, andAir Canada from Canada to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,491 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,491 reviews
United Airlines
7.4
Good
9,491 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,302 reviews
United Airlines
7.4
Good
9,491 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,844 reviews
United Airlines
7.4
Good
9,491 reviews
Check prices

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Crew

8.1

Comfort

7.3

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

Related info for your journey

Find useful and relevant information for your journey from Canada to Chesapeake. 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 Canada to Chesapeake?

    Departing from Canada to Chesapeake will take you 4h 20m. There are 938 km between Canada and Chesapeake. Both multi-stop and direct flights can be found to your destination and back.

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

    The most popular route from Canada to Chesapeake is Montreal Pierre Elliott Trudeau Intl - Norfolk. You may also consider Toronto Pearson Intl - Norfolk or Vancouver Intl - Norfolk.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Canada to Chesapeake 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 Canada to Chesapeake?

    Currently, April is the cheapest month in which you can book a flight from Canada to Chesapeake (average of C$ 253). Flying from Canada to Chesapeake in November is currently the most expensive (average of C$ 540). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Canada to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Reagan-National flights
Pearson Intl to Dulles Intl flights
Toronto Island to Dulles Intl flights
Vancouver Intl to Dulles Intl flights
Pierre Elliott Trudeau Intl to Reagan-National flights
Pierre Elliott Trudeau Intl to Dulles Intl flights
Vancouver Intl to Reagan-National flights
Ottawa to Dulles Intl flights
Pearson Intl to Raleigh flights
Toronto Island to Reagan-National flights
Ottawa to Reagan-National flights
Pierre Elliott Trudeau Intl to Raleigh flights
Calgary to Dulles Intl flights
Calgary to Reagan-National flights
Toronto Island to Raleigh flights
Seattle to Reagan-National flights
Pearson Intl to Norfolk flights
Pierre Elliott Trudeau Intl to Norfolk flights
Winnipeg to Dulles Intl flights
Edmonton to Dulles Intl flights
Edmonton to Reagan-National flights
Pearson Intl to Richmond flights
Vancouver Intl to Raleigh flights
Pearson Intl to Greensboro flights
Buffalo to Raleigh flights
Halifax to Dulles Intl flights
Winnipeg to Reagan-National flights
Calgary to Raleigh flights
Halifax to Reagan-National flights
Pierre Elliott Trudeau Intl to Richmond flights
Québec City to Dulles Intl flights
Ottawa to Raleigh flights
Pierre Elliott Trudeau Intl to Greensboro flights
Halifax to Raleigh flights
Victoria to Dulles Intl flights
Victoria to Reagan-National flights
Québec City to Reagan-National flights
London to Dulles Intl flights
Kelowna to Dulles Intl flights
Vancouver Intl to Richmond flights
Vancouver Intl to Norfolk flights
Saskatoon to Reagan-National flights
Kelowna to Reagan-National flights
London to Reagan-National flights
Calgary to Norfolk flights

Top 3 airlines flying from Canada to Chesapeake

Discover the top 3 airlines that operate flights from Canada to Chesapeake. 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 629,999 searches. Data last updated 27 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 232AverageC$ 825FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 282AverageC$ 718FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 457AverageC$ 722FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Canada to Chesapeake?

When you search for this flight from Canada to Chesapeake, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Canada to Chesapeake?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chesapeake from Canada.

Can Cheapflights find flights from Canada to Chesapeake with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Canada to Chesapeake, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Canada to Chesapeake become cheaper?

Yes, Cheapflights offers price alerts on Canada to Chesapeake flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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