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C$ 282+ 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 24/9. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
30 Aug — 6 Sep1
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 31 July 2026.

Sun 13/94:50 p.m.
YYZ
-
ORF
1 stop25h 58m
Multiple Airlines
Wed 23/98:00 a.m.
ORF
-
YYZ
2 stops36h 55m
Multiple Airlines
Deal found 29/7C$ 528
Tue 8/94:05 p.m.
YYZ
-
ORF
1 stop7h 28m
Delta
Tue 15/910:00 a.m.
ORF
-
YYZ
1 stop6h 13m
Delta
Deal found 29/7C$ 560
Tue 8/910:45 a.m.
YYZ
-
ORF
2 stops12h 58m
United Airlines
Tue 15/96:15 a.m.
ORF
-
YYZ
1 stop3h 49m
United Airlines
Deal found 29/7C$ 570
Sun 6/912:45 p.m.
YYZ
-
ORF
1 stop10h 58m
United Airlines
Tue 8/95:02 p.m.
ORF
-
YYZ
1 stop6h 57m
United Airlines
Deal found 27/7C$ 578
Wed 9/93:00 p.m.
YYZ
-
ORF
2 stops8h 43m
United Airlines
Sat 12/95:02 p.m.
ORF
-
YYZ
1 stop6h 57m
United Airlines
Deal found 29/7C$ 582
Fri 9/107:15 a.m.
YYZ
-
ORF
1 stop7h 12m
American Airlines
Wed 14/106:00 a.m.
ORF
-
YYZ
1 stop5h 59m
American Airlines
Deal found 27/7C$ 584
Fri 14/84:10 p.m.
YYZ
-
ORF
1 stop7h 32m
Delta
Sun 16/81:51 p.m.
ORF
-
YYZ
1 stop10h 06m
Delta
Deal found 29/7C$ 595
Fri 4/97:43 p.m.
YYZ
-
ORF
1 stop4h 00m
United Airlines
Sun 13/96:15 a.m.
ORF
-
YYZ
1 stop3h 49m
United Airlines
Deal found 26/7C$ 596
Fri 14/83:19 p.m.
YYZ
-
ORF
1 stop7h 45m
American Airlines
Sun 16/86:01 a.m.
ORF
-
YYZ
1 stop7h 25m
American Airlines
Deal found 29/7C$ 602
Thu 8/102:30 p.m.
YYZ
-
ORF
1 stop9h 14m
United Airlines
Mon 12/106:15 a.m.
ORF
-
YYZ
1 stop8h 04m
United Airlines
Deal found 27/7C$ 603

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 31 July 2026.

Round-trip from

C$ 528

One-way from

C$ 282

Popular in

August

Cheapest in

May

Average price

C$ 756
13/9-23/9
  • 13/9-23/9
  • 3 total stops
  • 62h 53m total
  • Toronto to Norfolk
Search Deals
24/9
  • 24/9
  • 2 total stops
  • 33h 13m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 31 July 2026.
Use the filters below to find and compare flights to Chesapeake that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 13/9

4:50 p.m.-6:48 p.m.

1 stop25h 58m

Norfolk

Wed 23/9

8:00 a.m.-8:55 p.m.

2 stops36h 55m

C$ 554

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 9/9

9:44 a.m.-2:15 p.m.

1 stop4h 31m

Norfolk

Sat 12/9

5:02 p.m.-11:59 p.m.

1 stop6h 57m

C$ 560

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 12/9

6:15 a.m.-3:56 p.m.

1 stop9h 41m

Norfolk

Sat 19/9

6:00 a.m.-11:18 a.m.

1 stop5h 18m

C$ 560

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 14/8

4:10 p.m.-11:42 p.m.

1 stop7h 32m

Norfolk

Sun 16/8

1:51 p.m.-11:57 p.m.

1 stop10h 06m

C$ 595

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 8/10

6:00 a.m.-1:45 p.m.

1 stop7h 45m

Norfolk

Mon 12/10

3:13 p.m.-11:59 p.m.

1 stop8h 46m

C$ 595
Quickest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 4/9

7:43 p.m.-11:43 p.m.

1 stop4h 00m

Norfolk

Sun 13/9

6:15 a.m.-10:04 a.m.

1 stop3h 49m

C$ 596

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 16/10

6:10 p.m.-11:32 p.m.

1 stop5h 22m

Norfolk

Sun 18/10

5:25 p.m.-11:29 p.m.

1 stop6h 04m

C$ 596

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 8/10

2:30 p.m.-11:44 p.m.

1 stop9h 14m

Norfolk

Mon 12/10

6:15 a.m.-2:19 p.m.

1 stop8h 04m

C$ 603
Cheapest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 24/9

1:30 p.m.-10:43 p.m.

2 stops33h 13m

C$ 282

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 9/9

9:30 a.m.-12:29 p.m.

2 stops26h 59m

C$ 302

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/7

Showing 1-10 of 16 resultsSorted by cheapest first
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 7 hours 32 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, Air Canada and American Airlines.

United Airlines
United Airlines
From C$ 440
WestJet
WestJet
From C$ 587
Air Canada
Air Canada
From C$ 416
American Airlines
American Airlines
From C$ 586

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are Air Canada, American Airlines 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 31 July 2026.
Get a feel of what it's like to fly with United Airlines 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
10,053 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.7

Overall

7.4

Comfort

7.3

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
10,053 reviews
United Airlines
7.4
Good
10,053 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.7

Overall

7.4

Comfort

7.3

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, United Airlines 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 (3 hours 57 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?

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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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