Find flights
When to book
Airlines
FAQs

Cheap flights from Toronto to Chesapeake from C$ 165

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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
YTO — RIC
27 Jan — 3 Feb1
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 28 December 2025.

Sat 27/124:44 p.m.YYZ - ORF
1 stop4h 47mAmerican Airlines
Mon 5/15:26 p.m.ORF - YYZ
1 stop4h 17mAmerican Airlines
Deal found 26/12C$ 1,007
Sat 27/129:25 a.m.YYZ - ORF
2 stops52h 41mMultiple Airlines
Mon 5/17:40 p.m.ORF - YYZ
1 stop28h 31mMultiple Airlines
Deal found 26/12C$ 1,070
Sat 27/122:15 p.m.YYZ - ORF
1 stop9h 26mAir Canada
Sun 28/127:55 p.m.ORF - YYZ
1 stop3h 51mAir Canada
Deal found 25/12C$ 1,155
Sat 27/126:30 p.m.YYZ - ORF
2 stops24h 00mWestJet
Mon 5/112:10 p.m.ORF - YYZ
2 stops33h 01mWestJet
Deal found 26/12C$ 1,312
Sat 27/1211:00 a.m.YYZ - ORF
2 stops27h 39mWestJet
Sun 28/124:50 p.m.ORF - YYZ
1 stop6h 00mWestJet
Deal found 26/12C$ 1,328
Sat 27/126:00 a.m.YYZ - ORF
1 stop9h 50mAmerican Airlines
Sun 28/127:20 p.m.ORF - YYZ
1 stop3h 37mAmerican Airlines
Deal found 26/12C$ 1,488

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 28 December 2025.

Round-trip from

C$ 332

One-way from

C$ 165

Popular in

August

Cheapest in

February

Average price

C$ 585
15/1-29/1
  • 15/1-29/1
  • 3 total stops
  • 31h 48m total
  • Toronto to Chesapeake
Search Deals
9/2
  • 9/2
  • 1 total stop
  • 11h 38m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 159 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 December 2025
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 28 December 2025.
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

Thu 15/1

7:15 a.m.-4:44 p.m.

2 stops9h 29m

Norfolk

Thu 29/1

4:01 p.m.-2:20 p.m.

1 stop22h 19m

C$ 332

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 12/1

9:35 a.m.-6:38 p.m.

1 stop9h 03m

Norfolk

Thu 15/1

7:33 p.m.-2:40 p.m.

1 stop19h 07m

C$ 343

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 29/5

9:50 a.m.-10:38 p.m.

1 stop12h 48m

Norfolk

Mon 1/6

8:24 p.m.-2:05 p.m.

1 stop17h 41m

C$ 462

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 15/1

6:06 a.m.-2:57 p.m.

1 stop8h 51m

Norfolk

Mon 19/1

6:05 a.m.-5:53 p.m.

1 stop11h 48m

C$ 515

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 25/1

7:30 a.m.-11:44 a.m.

1 stop4h 14m

Norfolk

Sun 1/2

10:05 a.m.-4:02 p.m.

1 stop5h 57m

C$ 678

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 29/5

12:05 p.m.-11:36 p.m.

3 stops11h 31m

Norfolk

Mon 1/6

11:29 a.m.-6:59 p.m.

1 stop7h 30m

C$ 752

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 19/6

6:15 a.m.-12:43 p.m.

1 stop6h 28m

Norfolk

Fri 26/6

6:05 p.m.-12:04 a.m.

1 stop5h 59m

C$ 754

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 9/2

7:00 a.m.-6:38 p.m.

1 stop11h 38m

C$ 165

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 11/2

7:15 a.m.-6:26 p.m.

2 stops35h 11m

C$ 272

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/12

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$ 275). Flying from Toronto to Chesapeake in November is currently the most expensive (average of C$ 741). 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 28 December 2025.
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
9,113 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

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
9,113 reviews
United Airlines
7.4
Good
9,113 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

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
3,222 reviews
United Airlines
7.4
Good
9,113 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

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
10,562 reviews
United Airlines
7.4
Good
9,113 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Overall

7.4

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$ 275). Flying from Toronto to Chesapeake in November is currently the most expensive (average of C$ 741). 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

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

Alternative routes for Toronto to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to Dulles Intl flights
Pearson Intl to Reagan-National flights
Toronto Island to Dulles Intl flights
Pierre Elliott Trudeau Intl to Dulles Intl flights
Pierre Elliott Trudeau Intl to Reagan-National flights
Pearson Intl to Raleigh flights
Ottawa to Dulles Intl flights
Toronto Island to Reagan-National flights
Ottawa to Reagan-National flights
Pierre Elliott Trudeau Intl to Raleigh flights
Pearson Intl to Norfolk flights
Toronto Island to Raleigh flights
Pearson Intl to Roanoke flights
Pearson Intl to Richmond flights
Pearson Intl to Charlottesville flights
Thunder Bay to Dulles Intl flights
Pearson Intl to Greensboro flights
Pierre Elliott Trudeau Intl to Norfolk flights
Ottawa to Raleigh flights
Pierre Elliott Trudeau Intl to Charlottesville flights
Ottawa to Norfolk flights
Pearson Intl to Newport News flights
Pierre Elliott Trudeau Intl to Greensboro flights
Pearson Intl to Blountville flights
London to Dulles Intl flights
London to Reagan-National flights
Pierre Elliott Trudeau Intl to Richmond flights
Pierre Elliott Trudeau Intl to Lynchburg flights
Hamilton to Reagan-National flights
Pierre Elliott Trudeau Intl to Staunton flights

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 28 December 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 345AverageC$ 663FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapestC$ 360AverageC$ 429FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 361AverageC$ 737FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 361AverageC$ 751FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 435AverageC$ 704FlexibilityNo 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 Toronto to Chesapeake?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chesapeake from Toronto today with Cheapflights!

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Toronto to Chesapeake for you. Better yet — we are completely free to use.

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Toronto to Chesapeake flexibly with Cheapflights today.

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

Of course! You can now track prices for flights from Toronto to Chesapeake and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.