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C$ 167+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
19 Jan — 26 Jan1
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 20 December 2025.

Sun 21/126:10 a.m.YYZ - ORF
1 stop8h 29mWestJet
Sun 4/14:50 p.m.ORF - YYZ
1 stop16h 14mWestJet
Deal found 19/12C$ 950
Sun 21/129:00 a.m.YYZ - ORF
1 stop5h 10mUnited Airlines
Sun 4/17:55 p.m.ORF - YYZ
1 stop23h 02mUnited Airlines
Deal found 18/12C$ 964
Sat 27/127:30 a.m.YYZ - ORF
1 stop6h 50mAmerican Airlines
Sun 28/125:28 p.m.ORF - YYZ
1 stop4h 15mAmerican Airlines
Deal found 19/12C$ 990
Sun 21/1210:58 a.m.YYZ - ORF
1 stop12h 03mAmerican Airlines
Sun 4/15:16 p.m.ORF - YYZ
1 stop4h 27mAmerican Airlines
Deal found 17/12C$ 1,013
Sat 27/1210:00 a.m.YYZ - ORF
1 stop13h 41mUnited Airlines
Sun 28/1210:46 a.m.ORF - YYZ
1 stop13h 00mUnited Airlines
Deal found 17/12C$ 1,041
Sat 20/123:40 p.m.YYZ - ORF
1 stop22h 26mMultiple Airlines
Sun 21/129:45 p.m.ORF - YYZ
2 stops26h 04mMultiple Airlines
Deal found 19/12C$ 1,064
Sat 20/126:10 a.m.YYZ - ORF
1 stop12h 35mWestJet
Sun 21/127:10 a.m.ORF - YYZ
1 stop4h 09mWestJet
Deal found 19/12C$ 1,136
Sat 27/126:10 a.m.YYZ - ORF
1 stop12h 35mWestJet
Sun 28/128:00 a.m.ORF - YYZ
2 stops31h 53mWestJet
Deal found 19/12C$ 1,227

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 20 December 2025.

Round-trip from

C$ 361

One-way from

C$ 167

Popular in

August

Cheapest in

February

Average price

C$ 590
8/1-14/1
  • 8/1-14/1
  • 2 total stops
  • 24h 17m total
  • Toronto to Norfolk
Search Deals
2/2
  • 2/2
  • 1 total stop
  • 11h 38m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 118 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).
Search Deals
Average for round-trip flights in December 2025
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 20 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

Thu 8/1

7:40 a.m.-6:38 p.m.

1 stop10h 58m

Norfolk

Wed 14/1

8:00 a.m.-9:19 p.m.

1 stop13h 19m

C$ 361

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 8/1

2:25 p.m.-10:06 p.m.

1 stop7h 41m

Norfolk

Mon 12/1

6:05 a.m.-4:12 p.m.

1 stop10h 07m

C$ 527

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 12/1

2:57 p.m.-7:00 p.m.

1 stop4h 03m

Norfolk

Wed 14/1

4:45 p.m.-11:59 p.m.

1 stop7h 14m

C$ 768

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 12/1

5:15 p.m.-11:15 p.m.

1 stop6h 00m

Norfolk

Wed 14/1

7:01 a.m.-11:17 a.m.

1 stop4h 16m

C$ 768

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 8/1

4:00 p.m.-9:52 a.m.

2 stops17h 52m

Norfolk

Wed 14/1

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

2 stops18h 25m

C$ 2,624

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 2/2

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

1 stop11h 38m

C$ 167

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 23/1

9:35 a.m.-6:38 p.m.

1 stop9h 03m

C$ 181

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/12

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 1 minute. 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.

When is the cheapest time to fly to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chesapeake. Price data was last updated on 16 December 2024.

Users looking for the lowest fares to Chesapeake should consider flying on Wednesday afternoons, when prices are typically cheapest. Budget-minded travellers will want to avoid Monday evenings, when prices are usually at their highest.

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$ 383
United Airlines
United Airlines
From C$ 368
Air Canada
Air Canada
From C$ 324
American Airlines
American Airlines
From C$ 400

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are Air Canada, United Airlines 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 20 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
9,096 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

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
9,096 reviews
United Airlines
7.4
Good
9,096 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

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
3,207 reviews
United Airlines
7.4
Good
9,096 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

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
10,547 reviews
United Airlines
7.4
Good
9,096 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

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, 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 1 minute).

  • 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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