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$303+ Cheap flights from Chesapeake, VA to Toronto (YTO)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — YTO
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap flight deals from Chesapeake to Toronto

Cheapest flights from Chesapeake to Toronto
Explore the most affordable flight options available from Chesapeake to Toronto. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:45 am
ORF
-
YYZ
2 stops16h 35m
Multiple Airlines
Wed 3/257:15 am
YYZ
-
ORF
1 stop14h 32m
Multiple Airlines
Deal found 2/1$303
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:41 pm
ORF
-
YYZ
2 stops17h 39m
Multiple Airlines
Thu 3/267:10 am
YYZ
-
ORF
1 stop14h 37m
Multiple Airlines
Deal found 2/2$335
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/76:45 am
ORF
-
YYZ
2 stops16h 35m
Multiple Airlines
Mon 3/23:40 pm
YYZ
-
ORF
1 stop26h 46m
Multiple Airlines
Deal found 2/2$385
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:31 pm
ORF
-
YYZ
1 stop27h 49m
Multiple Airlines
Fri 3/136:20 pm
YYZ
-
ORF
2 stops25h 26m
Multiple Airlines
Deal found 2/2$392
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:45 am
ORF
-
YYZ
1 stop7h 35m
Multiple Airlines
Sun 3/18:20 pm
YYZ
-
ORF
1 stop11h 44m
Multiple Airlines
Deal found 2/2$405
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/89:37 pm
ORF
-
YYZ
1 stop13h 49m
Multiple Airlines
Mon 2/93:40 pm
YYZ
-
ORF
1 stop26h 58m
Multiple Airlines
Deal found 2/2$413
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1211:46 am
ORF
-
YYZ
2 stops26h 34m
Multiple Airlines
Mon 2/168:30 pm
YYZ
-
ORF
1 stop21h 56m
Multiple Airlines
Deal found 2/2$435
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/76:45 am
ORF
-
YYZ
2 stops16h 35m
Multiple Airlines
Mon 2/93:40 pm
YYZ
-
ORF
1 stop26h 58m
Multiple Airlines
Deal found 2/2$440

Find flight deals from Chesapeake to Toronto

Keep the following information in mind while searching for Chesapeake to Toronto flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Kiwi.com)

Popular in

June

Cheapest in

February

Average price

$374
Provider with most accurate pricing for Norfolk-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Toronto (YTO) flights.
Search Deals
From Chesapeake to Toronto (YTO)
Search Deals
High demand for flights, 7% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Toronto 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 2,558,603 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from Chesapeake to Toronto that are best for you.

Fly from

Chesapeake

Fly to

Toronto

Route

Depart

Return

Price

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 3/18

6:45 am-11:20 pm

2 stops16h 35m

Toronto Pearson Intl

Wed 3/25

7:15 am-9:47 pm

1 stop14h 32m

$303

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Tue 3/24

8:41 pm-2:20 pm

2 stops17h 39m

Toronto Pearson Intl

Thu 3/26

7:10 am-9:47 pm

1 stop14h 37m

$335

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Mon 3/2

7:31 pm-11:20 pm

1 stop27h 49m

Toronto Pearson Intl

Fri 3/13

6:20 pm-7:46 pm

2 stops25h 26m

$392

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Mon 2/23

6:45 am-2:20 pm

1 stop7h 35m

Toronto Pearson Intl

Sun 3/1

8:20 pm-8:04 am

1 stop11h 44m

$405

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Fri 2/13

7:31 pm-2:40 pm

1 stop19h 09m

Toronto Pearson Intl

Mon 2/16

8:30 pm-6:26 pm

1 stop21h 56m

$452

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 7/29

9:06 am-4:25 pm

1 stop7h 19m

Toronto Pearson Intl

Mon 8/3

7:45 am-10:48 pm

1 stop15h 03m

$458

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 4/22

6:00 am-4:45 pm

1 stop10h 45m

Toronto Pearson Intl

Wed 4/29

11:10 am-10:06 pm

1 stop10h 56m

$485

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Sun 6/21

9:50 pm-12:16 pm

3 stops38h 26m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Best time to book a flight from Chesapeake to Toronto

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

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

Currently, June is the cheapest month in which you can book a flight from Chesapeake to Toronto (average of $129). Flying from Chesapeake to Toronto in November is currently the most expensive (average of $766). 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 Chesapeake to Toronto?

Reviews of airlines servicing Toronto

Get insights into the airlines that provide service to Toronto. 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 Toronto. Reviews last updated February 3, 2026.
Peruse reviews from past customers who have flown with American Airlines from Chesapeake to Toronto to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,216 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,216 reviews
American Airlines
7.2
Good
11,216 reviews

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Toronto. 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 Chesapeake to Toronto that include hotel bookings?

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Chesapeake to Toronto (average of $129). Flying from Chesapeake to Toronto in November is currently the most expensive (average of $766). 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 Chesapeake to Toronto

See prices for flight routes from nearby airports that may be better suited for you.
Reagan-National to Pearson Intl flights
Dulles Intl to Pearson Intl flights
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Dulles Intl to Kingston flights
Reagan-National to Hamilton flights
Reagan-National to Kingston flights

Top 3 airlines flying from Chesapeake to Toronto

Discover the top 3 airlines that operate flights from Chesapeake to Toronto. 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 2,558,603 searches. Data last updated February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$129Average$347FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$461FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$315Average$624FlexibilityNo cancel feeOn-time71%

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