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C$ 182+ 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 19/2. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
5 Feb — 12 Feb1
1 adult
1 adult, Economy, 0 bags

Flights to Chesapeake in 2026

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 6 January 2026.

Round-trip from

C$ 271

One-way from

C$ 182

Popular in

August

Cheapest in

December

Average price

C$ 686
2/2-9/2
  • 2/2-9/2
  • 2 total stops
  • 54h 45m total
  • Toronto to Norfolk
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19/2
  • 19/2
  • 1 total stop
  • 8h 21m total
  • Toronto to Chesapeake
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Highest demand for flights based on searches. 16% potential increase in price (C$ 126 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals to Chesapeake

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 6 January 2026.

Mon 2/23:40 p.m.YYZ - ORF
1 stop26h 58mMultiple Airlines
Mon 9/27:33 p.m.ORF - YYZ
1 stop27h 47mMultiple Airlines
Deal found 5/1C$ 271
Thu 26/210:05 a.m.YYZ - ORF
1 stop8h 21mMultiple Airlines
Wed 4/37:31 p.m.ORF - YYZ
1 stop24h 24mMultiple Airlines
Deal found 6/1C$ 277
Tue 20/13:40 p.m.YYZ - ORF
2 stops26h 45mMultiple Airlines
Mon 26/17:33 p.m.ORF - YYZ
1 stop27h 47mMultiple Airlines
Deal found 5/1C$ 278
Tue 3/23:40 p.m.YYZ - ORF
1 stop26h 58mMultiple Airlines
Mon 9/27:33 p.m.ORF - YYZ
1 stop27h 47mMultiple Airlines
Deal found 5/1C$ 295
Mon 2/27:00 a.m.YYZ - ORF
1 stop11h 38mMultiple Airlines
Thu 5/24:01 p.m.ORF - YYZ
1 stop22h 19mMultiple Airlines
Deal found 5/1C$ 297
Wed 4/23:40 p.m.YYZ - ORF
1 stop26h 58mMultiple Airlines
Mon 9/27:33 p.m.ORF - YYZ
1 stop27h 47mMultiple Airlines
Deal found 5/1C$ 300
Mon 2/27:00 a.m.YYZ - ORF
1 stop11h 38mMultiple Airlines
Fri 6/26:45 a.m.ORF - YYZ
1 stop7h 35mMultiple Airlines
Deal found 5/1C$ 308
Mon 2/27:00 a.m.YYZ - ORF
1 stop11h 38mMultiple Airlines
Wed 4/26:15 p.m.ORF - YYZ
1 stop17h 13mMultiple Airlines
Deal found 5/1C$ 346
Tue 3/211:15 a.m.YYZ - ORF
1 stop7h 23mMultiple Airlines
Thu 5/24:01 p.m.ORF - YYZ
1 stop22h 19mMultiple Airlines
Deal found 5/1C$ 351
Thu 22/17:15 a.m.YYZ - ORF
2 stops15h 11mMultiple Airlines
Mon 26/17:00 a.m.ORF - YYZ
1 stop14h 19mMultiple Airlines
Deal found 5/1C$ 354

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 6 January 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 26/2

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

1 stop8h 21m

Norfolk

Wed 4/3

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

1 stop24h 24m

C$ 277

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 2/2

7:00 a.m.-6:38 p.m.

1 stop11h 38m

Norfolk

Fri 6/2

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

1 stop7h 35m

C$ 308

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 3/2

11:15 a.m.-6:38 p.m.

1 stop7h 23m

Norfolk

Fri 6/2

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

1 stop7h 35m

C$ 362

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 26/2

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

1 stop8h 21m

Norfolk

Mon 2/3

7:31 p.m.-8:10 p.m.

2 stops24h 39m

C$ 376

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 5/2

2:20 p.m.-10:26 p.m.

1 stop8h 06m

Norfolk

Mon 9/2

7:33 p.m.-11:28 a.m.

1 stop15h 55m

C$ 398

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 20/3

3:40 p.m.-7:31 p.m.

1 stop27h 51m

Norfolk

Sun 29/3

7:05 a.m.-2:53 p.m.

1 stop7h 48m

C$ 402

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 22/1

7:15 a.m.-9:50 p.m.

2 stops14h 35m

Norfolk

Tue 27/1

8:05 a.m.-9:19 p.m.

1 stop13h 14m

C$ 414

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 19/2

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

1 stop8h 21m

C$ 182

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 25/1

3:40 p.m.-6:38 p.m.

1 stop26h 58m

C$ 241

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 12/4

8:00 p.m.-9:23 a.m.

1 stop13h 23m

C$ 268

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 13 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 8 hours 21 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$ 382
United Airlines
United Airlines
From C$ 368
Air Canada
Air Canada
From C$ 323
American Airlines
American Airlines
From C$ 399

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are United Airlines, Air Canada and American 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 6 January 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
9,132 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,132 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
WestJet
7.2
Good
3,235 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Air Canada
7.1
Good
10,597 reviews
United Airlines
7.4
Good
9,132 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

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, Delta 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, Ottawa offers the quickest one-way flight (5 hours 32 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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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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