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C$ 169+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
25 Dec — 1 Jan1
1 adult
1 adult, Economy, 0 bags

Find flight deals to Chesapeake

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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 25 November 2025.

Wed 10/122:20 p.m.YYZ - ORF
1 stop7h 43mMultiple Airlines
Wed 7/17:40 p.m.ORF - YYZ
1 stop18h 40mMultiple Airlines
Deal found 24/11C$ 378
Fri 12/122:20 p.m.YYZ - ORF
1 stop7h 58mMultiple Airlines
Sun 14/128:38 a.m.ORF - YYZ
2 stops11h 35mMultiple Airlines
Deal found 24/11C$ 470
Sat 13/127:00 a.m.YYZ - ORF
1 stop12h 16mMultiple Airlines
Sun 14/128:11 p.m.ORF - YYZ
3 stops20h 07mMultiple Airlines
Deal found 24/11C$ 508
Thu 27/117:35 a.m.YYZ - ORF
1 stop14h 54mMultiple Airlines
Thu 4/128:11 p.m.ORF - YYZ
1 stop15h 32mMultiple Airlines
Deal found 23/11C$ 539

Flights to Chesapeake in 2025

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 25 November 2025.

Round-trip from

C$ 326

One-way from

C$ 169

Popular in

August

Cheapest in

January

Average price

C$ 806
29/1-1/2
  • 29/1-1/2
  • 2 total stops
  • 22h 15m total
  • Toronto to Norfolk
Search Deals
11/12
  • 11/12
  • 1 total stop
  • 12h 16m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 159 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 25 November 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 29/1

7:10 a.m.-9:50 p.m.

1 stop14h 40m

Norfolk

Sun 1/2

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

1 stop7h 35m

C$ 326

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 10/12

2:20 p.m.-10:03 p.m.

1 stop7h 43m

Norfolk

Wed 7/1

7:40 p.m.-2:20 p.m.

1 stop18h 40m

C$ 378

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 12/12

2:20 p.m.-10:18 p.m.

1 stop7h 58m

Norfolk

Sun 14/12

8:38 a.m.-8:13 p.m.

2 stops11h 35m

C$ 470

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 15/3

11:15 p.m.-6:36 p.m.

2 stops19h 21m

Norfolk

Tue 24/3

7:31 p.m.-11:20 p.m.

1 stop27h 49m

C$ 498

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 13/12

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

1 stop12h 16m

Norfolk

Sun 14/12

8:38 a.m.-8:13 p.m.

2 stops11h 35m

C$ 532

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

5:59 p.m.-9:26 a.m.

1 stop15h 27m

C$ 542

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 11/12

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

1 stop12h 16m

C$ 169

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 7/1

5:15 p.m.-1:34 p.m.

1 stop20h 19m

C$ 198

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 17/3

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

2 stops14h 35m

C$ 241

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 18/12

8:20 p.m.-6:45 p.m.

1 stop22h 25m

C$ 418

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/11

Showing 1-10 of 13 results
1
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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 7 hours 43 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.

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, Air Canada and WestJet.

WestJet
WestJet
From C$ 392
United Airlines
United Airlines
From C$ 357
Air Canada
Air Canada
From C$ 331
American Airlines
American Airlines
From C$ 287

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are American Airlines, Air Canada and United 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 25 November 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
9,046 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,046 reviews
United Airlines
7.4
Good
9,046 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
WestJet
7.2
Good
3,173 reviews
United Airlines
7.4
Good
9,046 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Air Canada
7.1
Good
10,476 reviews
United Airlines
7.4
Good
9,046 reviews
Check prices

Entertainment

7.1

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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, Air Canada 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 (4 hours 6 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?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights to Chesapeake. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets to Chesapeake?

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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