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C$ 270+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
7 Feb — 14 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 8 January 2026.

Round-trip from

C$ 369

One-way from

C$ 270

Popular in

August

Cheapest in

December

Average price

C$ 688
1/2-4/2
  • 1/2-4/2
  • 2 total stops
  • 35h 27m total
  • Toronto to Norfolk
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12/4
  • 12/4
  • 1 total stop
  • 13h 23m total
  • Toronto to Chesapeake
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Highest demand for flights based on searches. 16% potential increase in price (C$ 127 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 8 January 2026.

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$ 278
Tue 20/12:15 p.m.YYZ - ORF
1 stop23h 11mMultiple Airlines
Thu 22/16:45 a.m.ORF - YYZ
1 stop7h 35mMultiple Airlines
Deal found 6/1C$ 352
Fri 6/28:20 p.m.YYZ - ORF
1 stop23h 55mMultiple Airlines
Sat 28/24:37 p.m.ORF - YYZ
1 stop7h 37mMultiple Airlines
Deal found 7/1C$ 370
Thu 26/210:05 a.m.YYZ - ORF
1 stop8h 21mMultiple Airlines
Sun 1/37:31 p.m.ORF - YYZ
2 stops28h 43mMultiple Airlines
Deal found 7/1C$ 394
Sun 22/28:00 p.m.YYZ - ORF
2 stops14h 42mMultiple Airlines
Tue 24/21:02 p.m.ORF - YYZ
1 stop11h 12mMultiple Airlines
Deal found 7/1C$ 395
Fri 6/28:20 p.m.YYZ - ORF
1 stop23h 55mMultiple Airlines
Fri 13/23:18 p.m.ORF - YYZ
1 stop8h 56mMultiple Airlines
Deal found 7/1C$ 404
Fri 20/33:40 p.m.YYZ - ORF
1 stop27h 51mMultiple Airlines
Sun 29/37:05 a.m.ORF - YYZ
1 stop7h 48mMultiple Airlines
Deal found 5/1C$ 406
Fri 23/13:50 p.m.YYZ - ORF
2 stops16h 10mMultiple Airlines
Mon 26/17:33 p.m.ORF - YYZ
1 stop23h 29mMultiple Airlines
Deal found 7/1C$ 426

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 8 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$ 278

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 20/1

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

1 stop23h 11m

Norfolk

Thu 22/1

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

1 stop7h 35m

C$ 352

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 6/2

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

1 stop23h 55m

Norfolk

Sat 28/2

4:37 p.m.-12:14 a.m.

1 stop7h 37m

C$ 370

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 26/2

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

1 stop8h 21m

Norfolk

Sun 1/3

7:31 p.m.-12:14 a.m.

2 stops28h 43m

C$ 394

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 22/2

8:00 p.m.-10:42 a.m.

2 stops14h 42m

Norfolk

Tue 24/2

1:02 p.m.-12:14 a.m.

1 stop11h 12m

C$ 395

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 6/2

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

1 stop23h 55m

Norfolk

Fri 13/2

3:18 p.m.-12:14 a.m.

1 stop8h 56m

C$ 404

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$ 404

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 12/4

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

1 stop13h 23m

C$ 270

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 21/2

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

2 stops14h 35m

C$ 272

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 12/4

7:43 p.m.-11:54 a.m.

2 stops16h 11m

C$ 560

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

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 6 hours 59 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$ 384
United Airlines
United Airlines
From C$ 369
Air Canada
Air Canada
From C$ 325
American Airlines
American Airlines
From C$ 401

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 8 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
9,139 reviews
Check prices

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews
Check prices

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
WestJet
7.2
Good
3,235 reviews
United Airlines
7.4
Good
9,139 reviews
Check prices

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
Air Canada
7.1
Good
10,603 reviews
United Airlines
7.4
Good
9,139 reviews
Check prices

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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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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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