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Cheap flights from Toronto to Chesapeake from C$ 251

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.
YTO — RIC
27 May — 3 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Toronto to Chesapeake

Enter your travel dates to find the best prices.

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

Sat 13/69:50 a.m.
YYZ
-
ORF
1 stop10h 50m
Multiple Airlines
Tue 16/69:35 p.m.
ORF
-
YYZ
1 stop19h 10m
Multiple Airlines
Deal found 27/4C$ 416
Thu 28/59:50 a.m.
YYZ
-
ORF
1 stop8h 59m
Multiple Airlines
Wed 3/612:06 p.m.
ORF
-
YYZ
2 stops35h 34m
Multiple Airlines
Deal found 27/4C$ 454
Thu 11/66:30 a.m.
YYZ
-
ORF
1 stop11h 09m
Multiple Airlines
Mon 15/66:42 p.m.
ORF
-
YYZ
1 stop19h 23m
Multiple Airlines
Deal found 27/4C$ 455
Thu 28/59:50 a.m.
YYZ
-
ORF
1 stop10h 27m
Multiple Airlines
Fri 5/66:42 p.m.
ORF
-
YYZ
1 stop19h 23m
Multiple Airlines
Deal found 26/4C$ 468
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$ 473
Tue 23/69:50 a.m.
YYZ
-
ORF
1 stop10h 50m
Multiple Airlines
Tue 30/69:35 p.m.
ORF
-
YYZ
1 stop22h 30m
Multiple Airlines
Deal found 26/4C$ 477
Sat 23/51:30 p.m.
YYZ
-
ORF
1 stop28h 09m
Multiple Airlines
Sat 30/512:00 p.m.
ORF
-
YYZ
2 stops27h 00m
Multiple Airlines
Deal found 25/4C$ 485

Find flight deals from Toronto to Chesapeake

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

Round-trip from

C$ 454

One-way from

C$ 251

Popular in

August

Cheapest in

December

Average price

C$ 643
28/5-3/6
  • 28/5-3/6
  • 3 total stops
  • 44h 33m total
  • Toronto to Chesapeake
Search Deals
8/6
  • 8/6
  • 2 total stops
  • 51h 16m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 28 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 Toronto 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 April 2026.
Use the filters below to find and compare flights from Toronto to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 28/5

9:50 a.m.-6:49 p.m.

1 stop8h 59m

Norfolk

Mon 1/6

6:34 p.m.-2:05 p.m.

1 stop19h 31m

C$ 477

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 22/5

7:45 a.m.-8:17 p.m.

1 stop12h 32m

Norfolk

Tue 26/5

12:06 p.m.-8:30 p.m.

2 stops32h 24m

C$ 493

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 7/6

5:45 p.m.-8:17 p.m.

1 stop26h 32m

Norfolk

Sun 14/6

9:35 p.m.-8:05 p.m.

1 stop22h 30m

C$ 538

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 11/7

1:30 p.m.-9:58 a.m.

1 stop20h 28m

Norfolk

Wed 15/7

9:06 a.m.-4:45 p.m.

1 stop7h 39m

C$ 604

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 2/6

10:00 a.m.-6:03 p.m.

1 stop8h 03m

Norfolk

Sat 6/6

2:30 p.m.-9:10 a.m.

1 stop18h 40m

C$ 613

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 28/5

2:30 p.m.-10:43 p.m.

1 stop8h 13m

Norfolk

Wed 3/6

6:02 a.m.-4:12 p.m.

1 stop10h 10m

C$ 613

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 23/5

6:00 a.m.-4:23 p.m.

1 stop10h 23m

Norfolk

Sat 30/5

6:00 a.m.-1:30 p.m.

1 stop7h 30m

C$ 615

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 22/5

2:45 p.m.-9:37 p.m.

1 stop6h 52m

Norfolk

Tue 26/5

5:44 p.m.-10:23 p.m.

1 stop4h 39m

C$ 619
Quickest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 14/6

8:50 a.m.-3:43 p.m.

1 stop6h 53m

Norfolk

Sun 28/6

6:05 a.m.-10:04 a.m.

1 stop3h 59m

C$ 641
Cheapest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 8/6

8:10 a.m.-11:26 a.m.

2 stops51h 16m

C$ 251

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/4

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Toronto to Chesapeake

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

How much does it cost to fly round-trip from Toronto to Chesapeake?

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 April 2026.
Read reviews from past customers who have flown United Airlines and WestJet from Toronto to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,672 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

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
9,672 reviews
United Airlines
7.4
Good
9,672 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

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
9,672 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.6

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 Toronto to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto 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.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Toronto to Chesapeake

Discover the top 3 airlines that operate flights from Toronto 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 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 393AverageC$ 761FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 404AverageC$ 859FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 557AverageC$ 932FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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