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C$ 232+ Cheap flights to Chesapeake

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 25/3. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
20 Mar — 27 Mar1
1 adult
1 adult, Economy, 0 bags

Flights to Chesapeake in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Chesapeake
Explore the most affordable flight options available to Chesapeake. Find the lowest fares based on data from user searches, with prices last updated on 18 February 2026.

Thu 19/37:10 a.m.
YYZ
-
ORF
1 stop14h 37m
Multiple Airlines
Thu 26/36:45 a.m.
ORF
-
YYZ
1 stop7h 35m
Multiple Airlines
Deal found 14/2C$ 394
Thu 4/67:45 a.m.
YYZ
-
ORF
1 stop9h 06m
Multiple Airlines
Sun 7/68:27 p.m.
ORF
-
YYZ
2 stops23h 17m
Multiple Airlines
Deal found 16/2C$ 465
Sun 1/38:00 p.m.
YYZ
-
ORF
2 stops14h 42m
Multiple Airlines
Thu 12/38:41 p.m.
ORF
-
YYZ
1 stop25h 34m
Multiple Airlines
Deal found 14/2C$ 484
Fri 22/59:30 a.m.
YYZ
-
ORF
1 stop7h 21m
Multiple Airlines
Sun 24/58:27 p.m.
ORF
-
YYZ
2 stops23h 17m
Multiple Airlines
Deal found 17/2C$ 487
Sat 25/411:15 a.m.
YYZ
-
ORF
1 stop8h 17m
Multiple Airlines
Sat 2/511:19 a.m.
ORF
-
YYZ
2 stops24h 16m
Multiple Airlines
Deal found 16/2C$ 494
Tue 10/33:40 p.m.
YYZ
-
ORF
1 stop26h 46m
Multiple Airlines
Tue 17/36:45 a.m.
ORF
-
YYZ
1 stop7h 35m
Multiple Airlines
Deal found 15/2C$ 504
Sun 7/67:45 a.m.
YYZ
-
ORF
1 stop9h 06m
Multiple Airlines
Wed 10/612:16 p.m.
ORF
-
YYZ
1 stop7h 49m
Multiple Airlines
Deal found 15/2C$ 516
Sat 21/38:20 p.m.
YYZ
-
ORF
1 stop15h 20m
Multiple Airlines
Sat 28/33:26 p.m.
ORF
-
YYZ
1 stop8h 48m
Multiple Airlines
Deal found 14/2C$ 543

Find flight deals to Chesapeake

Find the latest flights to Chesapeake in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 18 February 2026.

Round-trip from

C$ 352

One-way from

C$ 232

Popular in

August

Cheapest in

December

Average price

C$ 662
16/4-20/4
  • 16/4-20/4
  • 2 total stops
  • 41h 14m total
  • Toronto to Norfolk
Search Deals
25/3
  • 25/3
  • 1 total stop
  • 14h 37m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Locate flights to Chesapeake that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 18 February 2026.
Use the filters below to find and compare flights to Chesapeake that are best for you.

Fly from

Toronto

Route

Depart

Return

Price

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 19/3

7:10 a.m.-9:47 p.m.

1 stop14h 37m

Norfolk

Thu 26/3

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

1 stop7h 35m

C$ 394

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 4/6

7:45 a.m.-4:51 p.m.

1 stop9h 06m

Norfolk

Sun 7/6

8:27 p.m.-7:44 p.m.

2 stops23h 17m

C$ 465

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 1/3

8:00 p.m.-10:42 a.m.

2 stops14h 42m

Norfolk

Thu 12/3

8:41 p.m.-10:15 p.m.

1 stop25h 34m

C$ 484

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 22/5

9:30 a.m.-4:51 p.m.

1 stop7h 21m

Norfolk

Sun 24/5

8:27 p.m.-7:44 p.m.

2 stops23h 17m

C$ 487

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 25/4

11:15 a.m.-7:32 p.m.

1 stop8h 17m

Norfolk

Sat 2/5

11:19 a.m.-11:35 a.m.

2 stops24h 16m

C$ 494

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 7/6

7:45 a.m.-4:51 p.m.

1 stop9h 06m

Norfolk

Wed 10/6

12:16 p.m.-8:05 p.m.

1 stop7h 49m

C$ 516

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 10/3

3:40 p.m.-6:26 p.m.

1 stop26h 46m

Norfolk

Tue 17/3

6:45 a.m.-7:35 p.m.

2 stops12h 50m

C$ 525

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 21/3

8:20 p.m.-11:40 a.m.

1 stop15h 20m

Norfolk

Sat 28/3

3:26 p.m.-12:14 a.m.

1 stop8h 48m

C$ 543

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 1/5

7:10 a.m.-5:49 p.m.

1 stop10h 39m

Norfolk

Sat 16/5

11:19 a.m.-11:35 a.m.

2 stops24h 16m

C$ 564

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 25/3

7:10 a.m.-9:47 p.m.

1 stop14h 37m

C$ 232

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/2

Showing 1-10 of 14 results
1
2

Best time to book a flight to Chesapeake

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

How long is the flight to Chesapeake?

On average, a flight from Toronto to Chesapeake takes 5 hours 20 minutes. Flights to Chesapeake from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

What are the most popular airlines that fly to Chesapeake?

The most popular airlines flying from Toronto to Chesapeake are United Airlines, WestJet and Air Canada.

WestJet
WestJet
From C$ 342
United Airlines
United Airlines
From C$ 396
Air Canada
Air Canada
From C$ 387
American Airlines
American Airlines
From C$ 236

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are American Airlines, Air Canada and United Airlines.

Rainfall in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chesapeake ranges from 74.0 - 148.0 mm per month. July is typically the wettest month, when rainfall can reach 148.0 mm. November is typically the driest time to visit Chesapeake when rainfall is around 74.0 mm.

Temperature in Chesapeake by month

Plan your trip to Chesapeake by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chesapeake, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 26.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 6.0 C).

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 18 February 2026.
Get a feel of what it's like to fly with United Airlines,WestJet, andAir Canada to the United States by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,312 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,312 reviews
United Airlines
7.4
Good
9,312 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
WestJet
7.2
Good
3,268 reviews
United Airlines
7.4
Good
9,312 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,732 reviews
United Airlines
7.4
Good
9,312 reviews
Check prices

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

FAQs about flying to Chesapeake

  • Can I find cheaper flights to Chesapeake if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chesapeake on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Chesapeake?

    Based on reviews from Cheapflights users, Air Canada is rated the highest out of the airlines that fly to Chesapeake.

  • Where does the fastest flight to Chesapeake depart from?

    For those looking to save time traveling to Chesapeake, Montreal offers the quickest one-way flight (4 hours 33 minutes).

  • Does Richmond Byrd Intl have rental cars?

    Yes. Those touching down at Richmond Byrd Intl can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Richmond Byrd Intl?

    Yes. Richmond Byrd Intl has hotels nearby for those requiring accommodations. Sheraton Richmond Airport Hotel is the closest property to Richmond Byrd Intl (1.6 km away from Richmond Byrd Intl).

See more FAQs

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How does Cheapflights help users find flights to Chesapeake?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights to Chesapeake. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights to Chesapeake.

Can Cheapflights find flights to Chesapeake with no change fees?

Yes, we can. To see specific flights to Chesapeake with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights offers price alerts on Chesapeake flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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