C$ 83+ 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 21/2. 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
14 Feb — 21 Feb1
1 adult
1 adult, Economy, 0 bags

Find flights from Chesapeake

Enter your travel dates to find the best prices.

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 15 January 2026.

Thu 29/16:45 a.m.
ORF
-
YOW
1 stop10h 28m
Multiple Airlines
Mon 2/24:15 p.m.
YOW
-
ORF
1 stop26h 23m
Multiple Airlines
Deal found 14/1C$ 360
Fri 30/16:45 a.m.
ORF
-
YYZ
1 stop7h 35m
Multiple Airlines
Sun 1/28:30 p.m.
YYZ
-
ORF
1 stop22h 08m
Multiple Airlines
Deal found 14/1C$ 367
Sun 8/37:31 p.m.
ORF
-
YYZ
1 stop28h 43m
Multiple Airlines
Thu 12/36:20 p.m.
YYZ
-
ORF
2 stops25h 26m
Multiple Airlines
Deal found 13/1C$ 457
Thu 19/27:31 p.m.
ORF
-
YUL
1 stop29h 14m
Multiple Airlines
Mon 23/24:35 p.m.
YUL
-
ORF
1 stop19h 30m
Multiple Airlines
Deal found 14/1C$ 474
Sat 28/24:37 p.m.
ORF
-
YYZ
1 stop7h 37m
Multiple Airlines
Sat 7/311:15 a.m.
YYZ
-
ORF
1 stop8h 34m
Multiple Airlines
Deal found 14/1C$ 474
Sun 1/27:45 p.m.
ORF
-
YOW
1 stop4h 09m
United Airlines
Thu 5/26:20 a.m.
YOW
-
ORF
1 stop8h 05m
United Airlines
Deal found 14/1C$ 484
Thu 29/17:33 p.m.
ORF
-
YQB
2 stops20h 25m
Multiple Airlines
Thu 5/26:15 a.m.
YQB
-
ORF
1 stop15h 35m
Multiple Airlines
Deal found 14/1C$ 485
Wed 25/38:41 p.m.
ORF
-
YYC
2 stops24h 28m
Multiple Airlines
Sat 28/312:30 a.m.
YYC
-
ORF
1 stop7h 54m
Multiple Airlines
Deal found 13/1C$ 492
Fri 27/26:45 a.m.
ORF
-
YOW
2 stops41h 54m
Multiple Airlines
Fri 6/34:20 p.m.
YOW
-
ORF
1 stop29h 30m
Multiple Airlines
Deal found 13/1C$ 492
Fri 27/26:45 a.m.
ORF
-
YYC
2 stops43h 20m
Multiple Airlines
Fri 6/34:20 p.m.
YYC
-
ORF
1 stop27h 30m
Multiple Airlines
Deal found 13/1C$ 510
Sat 28/28:44 p.m.
ORF
-
YVR
2 stops41h 28m
Multiple Airlines
Sat 7/310:30 p.m.
YVR
-
ORF
1 stop15h 56m
Multiple Airlines
Deal found 14/1C$ 529
Mon 2/311:39 a.m.
ORF
-
YYC
1 stop9h 30m
Multiple Airlines
Fri 6/34:20 p.m.
YYC
-
ORF
1 stop27h 30m
Multiple Airlines
Deal found 13/1C$ 531

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 15 January 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pearson Intl

Route

Depart

Return

Price

NorfolkOttawa

ORF - YOW

ORFYOW

Norfolk

Thu 29/1

6:45 a.m.-5:13 p.m.

1 stop10h 28m

Ottawa

Mon 2/2

4:15 p.m.-6:38 p.m.

1 stop26h 23m

C$ 360

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Fri 30/1

6:45 a.m.-2:20 p.m.

1 stop7h 35m

Toronto Pearson Intl

Sun 1/2

8:30 p.m.-6:38 p.m.

1 stop22h 08m

C$ 367

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Thu 12/2

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

1 stop19h 09m

Toronto Pearson Intl

Thu 19/2

10:05 a.m.-6:26 p.m.

1 stop8h 21m

C$ 393

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Sun 8/3

7:31 p.m.-12:14 a.m.

1 stop28h 43m

Toronto Pearson Intl

Thu 12/3

6:20 p.m.-7:46 p.m.

2 stops25h 26m

C$ 457

NorfolkOttawa

ORF - YOW

ORFYOW

Norfolk

Sun 1/2

7:45 p.m.-11:54 p.m.

1 stop4h 09m

Ottawa

Thu 5/2

6:20 a.m.-2:25 p.m.

1 stop8h 05m

C$ 484

NorfolkQuébec City

ORF - YQB

ORFYQB

Norfolk

Thu 29/1

7:33 p.m.-3:58 p.m.

2 stops20h 25m

Québec City

Thu 5/2

6:15 a.m.-9:50 p.m.

1 stop15h 35m

C$ 485

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Thu 19/2

7:31 p.m.-3:10 p.m.

1 stop19h 39m

Montreal Pierre Elliott Trudeau Intl

Mon 23/2

5:25 p.m.-6:26 p.m.

2 stops25h 01m

C$ 486

NorfolkToronto

ORF - YYZ

ORFYYZ

Norfolk

Sat 28/2

4:37 p.m.-11:35 a.m.

2 stops18h 58m

Toronto Pearson Intl

Sat 7/3

11:15 a.m.-7:49 p.m.

1 stop8h 34m

C$ 496

NorfolkMontreal

ORF - YUL

ORFYUL

Norfolk

Fri 27/2

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

2 stops41h 53m

Montreal Pierre Elliott Trudeau Intl

Fri 6/3

6:45 a.m.-6:26 p.m.

1 stop11h 41m

C$ 541

NorfolkHalifax

ORF - YHZ

ORFYHZ

Norfolk

Sat 30/5

6:00 a.m.-4:03 p.m.

1 stop9h 03m

Halifax Intl

Wed 3/6

2:50 p.m.-11:31 p.m.

1 stop9h 41m

C$ 550

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/1

Showing 1-10 of 42 results
1
2
3
...
5

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$ 179). Flying from Chesapeake in November will prove the most costly (average of C$ 1,065). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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.

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 15 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$ 38. While Madrid Barajas airport is usually cheaper if your destination is London with prices starting at C$ 46. 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$ 38 round trip
    Travel from Madrid to London from C$ 46 round trip
    Travel from Edmonton to Abbotsford from C$ 54 round trip
    Travel from Vancouver to Las Vegas from C$ 56 round trip
    Travel from Montreal to Halifax from C$ 57 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!

See more FAQs

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 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!

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.