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C$ 269+ Cheap flights to Chesapeake

— RIC
20 Sep — 27 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

Mon 14/91:50 p.m. -
2 stops28h 58m
Mon 21/97:00 a.m. -
1 stop7h 55m
Deal found 17/8C$ 520
Sat 12/99:30 a.m. -
2 stops26h 59m
Mon 21/97:00 a.m. -
1 stop7h 55m
Deal found 20/8C$ 529
Thu 29/107:15 a.m. -
1 stop10h 00m
Sun 1/117:30 a.m. -
1 stop8h 45m
Deal found 17/8C$ 532
Tue 10/117:15 a.m. -
1 stop10h 00m
Sun 15/1112:57 p.m. -
2 stops26h 23m
Deal found 16/8C$ 535
Mon 19/102:20 p.m. -
2 stops22h 14m
Fri 23/103:48 p.m. -
1 stop7h 47m
Deal found 16/8C$ 543
Thu 10/97:45 a.m. -
1 stop11h 03m
Wed 16/98:00 a.m. -
2 stops36h 55m
Deal found 19/8C$ 550
Tue 6/107:45 a.m. -
1 stop8h 35m
Wed 7/105:25 p.m. -
1 stop6h 04m
Deal found 17/8C$ 567
Mon 5/101:50 p.m. -
2 stops28h 58m
Mon 12/107:00 a.m. -
1 stop7h 55m
Deal found 20/8C$ 579
Thu 24/97:45 a.m. -
1 stop7h 19m
Sun 27/91:18 p.m. -
2 stops25h 37m
Deal found 19/8C$ 580

Find flight deals to Chesapeake

Round-trip from

C$ 520

One-way from

C$ 269

Popular in

August

Cheapest in

May

Average price

C$ 1,383
14/9-21/9
  • 14/9-21/9
  • 3 total stops
  • 36h 53m total
  • Toronto to Norfolk
Search Deals
18/9
  • 18/9
  • 2 total stops
  • 31h 40m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 167 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 55 potential savings vs. average RT price).
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Average for round-trip flights in August 2026
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Cheapflights Fare Finder

 
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 Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Tue 10/11

7:15 a.m.-5:15 p.m.

1 stop10h 00m

Norfolk

Sun 15/11

12:57 p.m.-3:20 p.m.

2 stops26h 23m

C$ 535

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Tue 6/10

7:45 a.m.-4:20 p.m.

1 stop8h 35m

Norfolk

Wed 7/10

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

1 stop6h 04m

C$ 567

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Sat 19/9

6:10 p.m.-11:33 p.m.

1 stop5h 23m

Norfolk

Mon 21/9

7:00 a.m.-2:55 p.m.

1 stop7h 55m

C$ 582
Quickest round-trip

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Tue 8/9

6:10 p.m.-11:33 p.m.

1 stop5h 23m

Norfolk

Tue 15/9

10:52 a.m.-5:19 p.m.

1 stop6h 27m

C$ 601

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Tue 8/9

6:30 a.m.-12:15 p.m.

2 stops29h 45m

Norfolk

Tue 15/9

7:43 p.m.-2:30 p.m.

1 stop18h 47m

C$ 609

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Sat 10/10

7:45 a.m.-4:20 p.m.

1 stop8h 35m

Norfolk

Sat 17/10

3:50 p.m.-2:55 p.m.

2 stops23h 05m

C$ 627

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Sat 12/9

10:45 a.m.-10:54 p.m.

1 stop12h 09m

Norfolk

Sat 19/9

6:02 a.m.-11:43 a.m.

1 stop5h 41m

C$ 637

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Sat 10/10

7:00 a.m.-3:16 p.m.

1 stop8h 16m

Norfolk

Sat 17/10

6:15 a.m.-7:02 p.m.

1 stop12h 47m

C$ 638

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Tue 6/10

3:00 p.m.-11:44 p.m.

2 stops8h 44m

Norfolk

Wed 7/10

1:00 p.m.-8:44 p.m.

1 stop7h 44m

C$ 638
Cheapest one-way

TorontoNorfolk

YYZ Toronto Pearson Intl - ORF Norfolk

YYZORF

Toronto Pearson Intl

Fri 18/9

8:10 a.m.-3:50 p.m.

2 stops31h 40m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/8

Showing 1-10 of 20 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

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 4 hours 18 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$ 432
WestJet
WestJet
From C$ 577
Air Canada
Air Canada
From C$ 409
American Airlines
American Airlines
From C$ 576

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

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

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 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
10,106 reviews
Check prices

Food

6.7

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

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
10,106 reviews
United Airlines
7.4
Good
10,106 reviews
Check prices

Food

6.7

Boarding

7.7

Comfort

7.3

Crew

8.1

Entertainment

7.1

Overall

7.4

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, Toronto offers the quickest one-way flight (4 hours 18 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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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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