C$ 100+ Cheap flights from Chesapeake

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 9/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
RIC — YYZ
28 Feb — 7 Mar1
1 adult
1 adult, Economy, 0 bags

Find flights from Chesapeake

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Cheapest flights from Chesapeake
Explore the most affordable flight options available from Chesapeake. Find the lowest fares based on data from user searches, with prices last updated on 29 January 2026.

Wed 4/37:31 p.m.
ORF
-
YYZ
1 stop24h 24m
Multiple Airlines
Wed 18/311:15 a.m.
YYZ
-
ORF
1 stop8h 31m
Multiple Airlines
Deal found 27/1C$ 334
Tue 21/46:05 a.m.
ORF
-
YYZ
1 stop8h 11m
Multiple Airlines
Sat 25/411:15 a.m.
YYZ
-
ORF
1 stop8h 14m
Multiple Airlines
Deal found 28/1C$ 384
Tue 21/46:05 a.m.
ORF
-
YYZ
1 stop8h 11m
Multiple Airlines
Fri 24/48:30 p.m.
YYZ
-
ORF
1 stop22h 59m
Multiple Airlines
Deal found 28/1C$ 394
Sun 19/48:24 p.m.
ORF
-
YUL
1 stop20h 04m
Multiple Airlines
Sat 25/48:00 a.m.
YUL
-
ORF
1 stop11h 29m
Multiple Airlines
Deal found 28/1C$ 429
Sun 15/38:41 p.m.
ORF
-
YYZ
2 stops27h 33m
Multiple Airlines
Sun 22/38:20 p.m.
YYZ
-
ORF
1 stop18h 11m
Multiple Airlines
Deal found 28/1C$ 430
Sat 14/36:45 a.m.
ORF
-
YYZ
1 stop15h 50m
Multiple Airlines
Sat 21/37:10 a.m.
YYZ
-
ORF
1 stop15h 22m
Multiple Airlines
Deal found 27/1C$ 440
Thu 12/38:41 p.m.
ORF
-
YUL
1 stop19h 39m
Multiple Airlines
Mon 16/35:25 p.m.
YUL
-
ORF
2 stops26h 21m
Multiple Airlines
Deal found 27/1C$ 486
Fri 13/36:45 a.m.
ORF
-
YUL
2 stops17h 53m
Multiple Airlines
Mon 16/38:00 a.m.
YUL
-
ORF
1 stop11h 46m
Multiple Airlines
Deal found 27/1C$ 489
Tue 17/36:45 a.m.
ORF
-
YUL
2 stops41h 53m
Multiple Airlines
Mon 23/38:00 a.m.
YUL
-
ORF
1 stop11h 46m
Multiple Airlines
Deal found 28/1C$ 497
Fri 13/36:45 a.m.
ORF
-
YOW
2 stops17h 54m
Multiple Airlines
Fri 20/39:30 a.m.
YOW
-
ORF
1 stop29h 01m
Multiple Airlines
Deal found 27/1C$ 501
Fri 17/46:05 a.m.
ORF
-
YHZ
2 stops16h 49m
Multiple Airlines
Sun 19/48:45 a.m.
YHZ
-
ORF
1 stop15h 14m
Multiple Airlines
Deal found 27/1C$ 516
Tue 24/36:10 a.m.
ORF
-
YOW
1 stop8h 17m
United Airlines
Fri 27/39:45 a.m.
YOW
-
ORF
1 stop14h 01m
United Airlines
Deal found 28/1C$ 517

Find flights from Chesapeake within your budget

 
Find flights departing from Chesapeake that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 29 January 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pearson Intl

Route

Depart

Return

Price

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Wed 4/3

7:31 p.m.-7:55 p.m.

1 stop24h 24m

Toronto Pearson Intl

Wed 18/3

11:15 a.m.-7:46 p.m.

1 stop8h 31m

C$ 334

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Tue 21/4

6:05 a.m.-2:16 p.m.

1 stop8h 11m

Toronto Pearson Intl

Sat 25/4

11:15 a.m.-7:29 p.m.

1 stop8h 14m

C$ 384

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Sun 19/4

8:24 p.m.-4:28 p.m.

1 stop20h 04m

Montreal Pierre Elliott Trudeau Intl

Sat 25/4

8:00 a.m.-7:29 p.m.

1 stop11h 29m

C$ 429

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Sun 15/3

8:41 p.m.-12:14 a.m.

2 stops27h 33m

Toronto Pearson Intl

Sun 22/3

8:20 p.m.-2:31 p.m.

1 stop18h 11m

C$ 430

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Tue 21/4

6:05 a.m.-2:16 p.m.

1 stop8h 11m

Toronto Pearson Intl

Fri 24/4

8:30 p.m.-4:53 p.m.

2 stops20h 23m

C$ 433

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Sat 14/3

6:45 a.m.-10:35 p.m.

1 stop15h 50m

Toronto Pearson Intl

Sat 21/3

7:10 a.m.-10:32 p.m.

1 stop15h 22m

C$ 440

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Thu 12/3

8:41 p.m.-4:20 p.m.

1 stop19h 39m

Montreal Pierre Elliott Trudeau Intl

Mon 16/3

5:25 p.m.-7:46 p.m.

2 stops26h 21m

C$ 486

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Fri 13/3

6:45 a.m.-12:38 a.m.

2 stops17h 53m

Montreal Pierre Elliott Trudeau Intl

Mon 16/3

8:00 a.m.-7:46 p.m.

1 stop11h 46m

C$ 489

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Tue 17/3

6:45 a.m.-12:38 a.m.

2 stops41h 53m

Montreal Pierre Elliott Trudeau Intl

Mon 23/3

8:00 a.m.-7:46 p.m.

1 stop11h 46m

C$ 497

NorfolkOttawa

ORF - YOW

ORFYOW

Norfolk

Fri 13/3

6:45 a.m.-12:39 a.m.

2 stops17h 54m

Ottawa

Fri 20/3

9:30 a.m.-2:31 p.m.

1 stop29h 01m

C$ 501

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

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Best time to book a flight from Chesapeake

Have a flexible travel schedule? Discover the best time to fly 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.

Travel insights for flights from Chesapeake

Get recent, data-driven insights about flights from Chesapeake including ideal travel times, pricing trends, and more.

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

Currently, June is the cheapest month in which you can book a flight from Chesapeake (average of C$ 175). Flying from Chesapeake in November will prove the most costly (average of C$ 1,040). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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Related info for your journey

Access useful and relevant information related to your journey from Chesapeake. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 29 January 2026.

  • Which is the cheapest airport to catch a flight from Chesapeake?

    The cheapest routes to Jeju City can be found at Busan Gimhae airport from C$ 37. While Madrid Barajas airport is usually cheaper if your destination is London with prices starting at C$ 45. Reference our flight search to find the best deals in real time.

  • What is the cheapest month to fly from Chesapeake?

    At the present moment the cheapest month to fly from Chesapeake is currently June; with November being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chesapeake?

    Check out the cheapest flights from Chesapeake to embark to:
    Travel from Busan to Jeju City from C$ 37 round trip
    Travel from Madrid to London from C$ 45 round trip
    Travel from Vancouver to Kelowna from C$ 56 round trip
    Travel from Paris to Porto from C$ 60 round trip
    Travel from Vancouver to Victoria from C$ 65 round trip

  • How does Cheapflights help users find flights from 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 from Chesapeake today with Cheapflights!

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

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

  • Can Cheapflights find flights from Chesapeake with no change fees?

    Certainly. Search results for flights from Chesapeake shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

    Yes, Cheapflights has a feature called Price Alerts, which offers users the ability to be notified when flight prices change. Track prices for your flight from Chesapeake today and book when you’re ready!

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How does Cheapflights help users find flights from 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 from Chesapeake today with Cheapflights!

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

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

Can Cheapflights find flights from Chesapeake with no change fees?

Certainly. Search results for flights from Chesapeake shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Yes, Cheapflights has a feature called Price Alerts, which offers users the ability to be notified when flight prices change. Track prices for your flight from Chesapeake today and book when you’re ready!

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