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C$ 246+ 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 23/1. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
29 Jan — 5 Feb1
1 adult
1 adult, Economy, 0 bags

Flights to Chesapeake in 2025

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 30 December 2025.

Tue 30/127:15 a.m.YYZ - ORF
1 stop7h 01mMultiple Airlines
Tue 30/127:40 p.m.ORF - YYZ
2 stops24h 23mMultiple Airlines
Deal found 30/12C$ 1,762

Find flight deals to Chesapeake

Find the latest flights to Chesapeake in 2025, 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 30 December 2025.

Round-trip from

C$ 428

One-way from

C$ 246

Popular in

August

Cheapest in

February

Average price

C$ 586
16/1-17/1
  • 16/1-17/1
  • 3 total stops
  • 17h 26m total
  • Toronto to Norfolk
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23/1
  • 23/1
  • 2 total stops
  • 25h 55m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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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 30 December 2025.
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

Fri 16/1

7:15 a.m.-5:06 p.m.

2 stops9h 51m

Norfolk

Sat 17/1

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

1 stop7h 35m

C$ 428

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 6/3

7:15 a.m.-2:31 p.m.

1 stop7h 16m

Norfolk

Mon 16/3

3:26 p.m.-2:20 p.m.

1 stop22h 54m

C$ 449

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 25/1

10:59 a.m.-11:05 p.m.

1 stop12h 06m

Norfolk

Sat 31/1

6:00 a.m.-4:35 p.m.

1 stop10h 35m

C$ 517

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 15/1

6:06 a.m.-2:57 p.m.

1 stop8h 51m

Norfolk

Mon 19/1

6:05 a.m.-5:53 p.m.

1 stop11h 48m

C$ 536

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 19/6

6:15 a.m.-12:43 p.m.

1 stop6h 28m

Norfolk

Fri 26/6

6:05 p.m.-12:04 a.m.

1 stop5h 59m

C$ 755

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 19/6

4:05 p.m.-11:31 p.m.

2 stops7h 26m

Norfolk

Fri 26/6

6:00 a.m.-10:41 a.m.

1 stop4h 41m

C$ 798

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 16/1

4:00 p.m.-9:53 a.m.

2 stops17h 53m

Norfolk

Sat 17/1

7:45 p.m.-2:10 p.m.

2 stops18h 25m

C$ 2,575

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 23/1

6:20 p.m.-8:15 p.m.

2 stops25h 55m

C$ 246

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 6/1

2:15 p.m.-1:26 p.m.

1 stop23h 11m

C$ 263

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 9/1

7:10 a.m.-5:06 p.m.

1 stop9h 56m

C$ 317

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/12

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 4 hours 5 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$ 380
United Airlines
United Airlines
From C$ 366
Air Canada
Air Canada
From C$ 321
American Airlines
American Airlines
From C$ 396

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 30 December 2025.
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
9,122 reviews
Check prices

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

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
9,122 reviews
United Airlines
7.4
Good
9,122 reviews
Check prices

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

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
3,226 reviews
United Airlines
7.4
Good
9,122 reviews
Check prices

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

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
10,564 reviews
United Airlines
7.4
Good
9,122 reviews
Check prices

Overall

7.4

Crew

8.1

Entertainment

7.1

Boarding

7.7

Food

6.6

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, Toronto offers the quickest one-way flight (4 hours 5 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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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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