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Cheap flights from Canada to Chesapeake from C$ 247

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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — RIC
26 May — 2 Jun1
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 26 April 2026.

Sat 30/56:00 a.m.
YOW
-
ORF
1 stop3h 34m
United Airlines
Wed 3/66:00 a.m.
ORF
-
YOW
1 stop15h 35m
United Airlines
Deal found 24/4C$ 418
Fri 3/76:00 a.m.
YOW
-
ORF
1 stop3h 39m
United Airlines
Tue 14/78:00 a.m.
ORF
-
YOW
1 stop5h 59m
United Airlines
Deal found 21/4C$ 439
Sat 29/88:05 a.m.
YEG
-
ORF
2 stops13h 38m
United Airlines
Wed 2/96:30 a.m.
ORF
-
YEG
1 stop11h 22m
United Airlines
Deal found 24/4C$ 470
Tue 19/57:00 a.m.
YYC
-
ORF
1 stop26h 11m
Multiple Airlines
Tue 26/512:06 p.m.
ORF
-
YYC
2 stops28h 39m
Multiple Airlines
Deal found 24/4C$ 470
Thu 28/59:50 a.m.
YYZ
-
ORF
1 stop10h 27m
Multiple Airlines
Thu 4/69:12 p.m.
ORF
-
YYZ
1 stop26h 23m
Multiple Airlines
Deal found 24/4C$ 474
Sun 30/812:40 p.m.
YWG
-
ORF
1 stop9h 54m
Delta
Wed 2/97:00 a.m.
ORF
-
YWG
2 stops14h 09m
Delta
Deal found 23/4C$ 474
Sat 24/108:30 a.m.
YWG
-
ORF
1 stop13h 59m
United Airlines
Wed 28/108:00 p.m.
ORF
-
YWG
2 stops16h 39m
United Airlines
Deal found 21/4C$ 476
Sun 24/56:30 a.m.
YYZ
-
ORF
1 stop11h 09m
Multiple Airlines
Sun 31/56:34 p.m.
ORF
-
YYZ
1 stop26h 21m
Multiple Airlines
Deal found 21/4C$ 477
Mon 17/88:10 a.m.
YYZ
-
ORF
1 stop14h 38m
Multiple Airlines
Thu 20/810:38 a.m.
ORF
-
YYZ
1 stop10h 02m
Multiple Airlines
Deal found 24/4C$ 482
Tue 9/69:50 a.m.
YYZ
-
ORF
1 stop10h 50m
Multiple Airlines
Tue 16/69:35 p.m.
ORF
-
YYZ
1 stop19h 10m
Multiple Airlines
Deal found 25/4C$ 484
Wed 27/512:30 a.m.
YYC
-
ORF
1 stop8h 41m
Multiple Airlines
Tue 2/612:06 p.m.
ORF
-
YYC
2 stops35h 49m
Multiple Airlines
Deal found 22/4C$ 484
Wed 27/57:00 a.m.
YYC
-
ORF
1 stop26h 11m
Multiple Airlines
Tue 2/612:06 p.m.
ORF
-
YYC
2 stops35h 49m
Multiple Airlines
Deal found 23/4C$ 485

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 26 April 2026.

Round-trip from

C$ 418

One-way from

C$ 247

Popular in

August

Cheapest in

December

Average price

C$ 645
United Airlines
  • United Airlines
  • 30/5-3/6
  • 2 total stops
  • 19h 09m total
  • Canada to Chesapeake
Search Deals
8/6
  • 8/6
  • 3 total stops
  • 50h 00m total
  • Canada to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 26 April 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

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Sat 30/5

6:00 a.m.-9:34 a.m.

1 stop3h 34m

Norfolk

Wed 3/6

6:00 a.m.-9:35 p.m.

1 stop15h 35m

C$ 418
Quickest round-trip

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Fri 3/7

6:00 a.m.-9:39 a.m.

1 stop3h 39m

Norfolk

Tue 14/7

8:00 a.m.-1:59 p.m.

1 stop5h 59m

C$ 439

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sun 30/8

12:40 p.m.-11:34 p.m.

1 stop9h 54m

Norfolk

Wed 2/9

7:00 a.m.-8:09 p.m.

2 stops14h 09m

C$ 474

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sun 30/8

7:00 a.m.-2:51 p.m.

1 stop6h 51m

Norfolk

Wed 2/9

6:30 a.m.-10:33 p.m.

1 stop17h 03m

C$ 474

CalgaryNorfolk

YYC - ORF

YYCORF

Calgary

Wed 27/5

12:30 a.m.-11:11 a.m.

1 stop8h 41m

Norfolk

Tue 2/6

12:06 p.m.-9:55 p.m.

2 stops35h 49m

C$ 485

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Tue 9/6

10:44 a.m.-9:37 p.m.

1 stop10h 53m

Norfolk

Sun 14/6

8:15 p.m.-9:11 a.m.

1 stop12h 56m

C$ 492

OttawaNorfolk

YOW - ORF

YOWORF

Ottawa

Sat 30/5

2:40 p.m.-11:44 p.m.

2 stops9h 04m

Norfolk

Wed 3/6

6:05 a.m.-2:17 p.m.

1 stop8h 12m

C$ 497

CalgaryNorfolk

YYC - ORF

YYCORF

Calgary

Sun 17/5

12:30 a.m.-11:11 a.m.

1 stop8h 41m

Norfolk

Thu 21/5

12:06 p.m.-11:00 a.m.

1 stop24h 54m

C$ 507

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 3/6

7:45 a.m.-9:45 p.m.

1 stop14h 00m

Norfolk

Sun 7/6

6:34 p.m.-5:09 p.m.

2 stops22h 35m

C$ 517

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 24/5

4:50 p.m.-11:11 a.m.

2 stops18h 21m

Norfolk

Sun 31/5

6:34 p.m.-8:55 p.m.

1 stop26h 21m

C$ 522

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/4

Showing 1-10 of 60 resultsSorted by cheapest first
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2
3
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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
No data available for this route at this time. Please check back soon.

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 26 April 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
9,656 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,656 reviews
United Airlines
7.4
Good
9,656 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
WestJet
7.2
Good
3,327 reviews
United Airlines
7.4
Good
9,656 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
Air Canada
7.1
Good
10,971 reviews
United Airlines
7.4
Good
9,656 reviews
Check prices

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 3h 34m. 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 Toronto Pearson Intl - Norfolk. You may also consider Montreal Pierre Elliott Trudeau Intl - Norfolk or Edmonton - 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.

See more FAQs

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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.
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Winnipeg to Reagan-National flights
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Pearson Intl to Richmond flights
Vancouver Intl to Richmond flights
Halifax to Reagan-National flights
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Pearson Intl to Norfolk flights
Seattle to Reagan-National flights
Québec City to Reagan-National flights
Halifax to Raleigh flights
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Saskatoon to Reagan-National flights
Pierre Elliott Trudeau Intl to Richmond flights
Ottawa to Raleigh flights
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St. John's to Dulles Intl flights
Québec City to Dulles Intl flights
Detroit to Raleigh flights
Calgary to Richmond flights
Calgary to Raleigh flights
St. John's to Reagan-National flights
Victoria to Dulles Intl flights
Fredericton to Dulles Intl flights
Edmonton to Norfolk flights
Vancouver Intl to Norfolk flights
Regina to Richmond flights
Pearson Intl to Roanoke flights
Vancouver Intl to Blountville 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 26 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 278AverageC$ 704FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 395AverageC$ 842FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 499AverageC$ 726FlexibilityNo 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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