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Cheap flights from Toronto to Chesapeake from C$ 236

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 29/1. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — RIC
1 Feb — 8 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Toronto to Chesapeake

Enter your travel dates to find the best prices.

Best flights from Toronto to Chesapeake
Discover carefully curated flight deals from Toronto to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 2 January 2026.

Mon 23/27:00 a.m.YYZ - ORF
1 stop11h 26mMultiple Airlines
Thu 26/27:31 p.m.ORF - YYZ
1 stop19h 09mMultiple Airlines
Deal found 30/12C$ 248
Wed 28/17:15 a.m.YYZ - ORF
2 stops31h 51mMultiple Airlines
Wed 4/26:15 p.m.ORF - YYZ
1 stop29h 05mMultiple Airlines
Deal found 30/12C$ 255
Fri 30/13:50 p.m.YYZ - ORF
1 stop30h 00mMultiple Airlines
Wed 4/26:15 p.m.ORF - YYZ
1 stop29h 05mMultiple Airlines
Deal found 30/12C$ 309
Sat 24/17:15 a.m.YYZ - ORF
1 stop13h 00mMultiple Airlines
Mon 26/17:33 p.m.ORF - YYZ
1 stop27h 47mMultiple Airlines
Deal found 31/12C$ 342
Fri 23/17:15 a.m.YYZ - ORF
2 stops14h 35mMultiple Airlines
Mon 26/17:33 p.m.ORF - YYZ
1 stop27h 47mMultiple Airlines
Deal found 31/12C$ 364

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 2 January 2026.

Round-trip from

C$ 248

One-way from

C$ 236

Popular in

August

Cheapest in

February

Average price

C$ 667
23/2-26/2
  • 23/2-26/2
  • 2 total stops
  • 30h 35m total
  • Toronto to Chesapeake
Search Deals
29/1
  • 29/1
  • 1 total stop
  • 14h 35m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 160 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 2 January 2026.
Use the filters below to find and compare flights from Toronto to Chesapeake that are best for you.

Fly from

Toronto

Fly to

Chesapeake

Route

Depart

Return

Price

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 23/2

7:00 a.m.-6:26 p.m.

1 stop11h 26m

Norfolk

Thu 26/2

7:31 p.m.-2:40 p.m.

1 stop19h 09m

C$ 248

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 28/1

7:15 a.m.-3:06 p.m.

2 stops31h 51m

Norfolk

Wed 4/2

6:15 p.m.-11:20 p.m.

1 stop29h 05m

C$ 255

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 30/1

3:50 p.m.-9:50 p.m.

1 stop30h 00m

Norfolk

Wed 4/2

6:15 p.m.-11:20 p.m.

1 stop29h 05m

C$ 309

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 24/1

7:15 a.m.-8:15 p.m.

1 stop13h 00m

Norfolk

Mon 26/1

7:33 p.m.-11:20 p.m.

1 stop27h 47m

C$ 342

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 23/1

7:15 a.m.-9:50 p.m.

2 stops14h 35m

Norfolk

Mon 26/1

7:33 p.m.-11:20 p.m.

1 stop27h 47m

C$ 364

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 29/1

7:15 a.m.-9:50 p.m.

1 stop14h 35m

C$ 236

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 28/1

3:15 p.m.-3:06 p.m.

2 stops23h 51m

C$ 243

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 30/1

6:20 p.m.-8:15 p.m.

2 stops25h 55m

C$ 255

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/12

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

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

Currently, May is the cheapest month in which you can book a flight from Toronto to Chesapeake (average of C$ 276). Flying from Toronto to Chesapeake in November is currently the most expensive (average of C$ 744). 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.

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 2 January 2026.
Read reviews from past customers who have flown United Airlines,WestJet, andAir Canada 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
9,132 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,132 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
WestJet
7.2
Good
3,230 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Air Canada
7.1
Good
10,574 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Entertainment

7.1

Crew

8.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Food

6.6

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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.

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

    Currently, May is the cheapest month in which you can book a flight from Toronto to Chesapeake (average of C$ 276). Flying from Toronto to Chesapeake in November is currently the most expensive (average of C$ 744). 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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Alternative routes for Toronto to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Toronto to Chesapeake

Discover the top 5 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 2 January 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapestC$ 266AverageC$ 475FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 346AverageC$ 666FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 362AverageC$ 740FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 362AverageC$ 780FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 437AverageC$ 707FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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

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

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