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C$ 223+ 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 27/11. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
16 Nov — 23 Nov1
1 adult
1 adult, Economy

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 17 October 2025.

Fri 5/122:20 p.m.YYZ - ORF
1 stop7h 58mMultiple Airlines
Fri 12/128:38 a.m.ORF - YYZ
1 stop29h 35mMultiple Airlines
Deal found 15/10C$ 420
Mon 15/122:20 p.m.YYZ - ORF
1 stop25h 21mMultiple Airlines
Thu 18/125:15 p.m.ORF - YYZ
1 stop6h 34mMultiple Airlines
Deal found 16/10C$ 451
Fri 7/1110:15 a.m.YYZ - ORF
1 stop12h 03mMultiple Airlines
Mon 10/114:57 p.m.ORF - YYZ
1 stop7h 28mMultiple Airlines
Deal found 14/10C$ 489
Sat 15/1110:15 a.m.YYZ - ORF
1 stop11h 48mMultiple Airlines
Sat 22/115:15 p.m.ORF - YYZ
1 stop6h 56mMultiple Airlines
Deal found 16/10C$ 522
Sun 2/117:10 a.m.YYZ - ORF
1 stop12h 58mMultiple Airlines
Mon 3/117:53 p.m.ORF - YYZ
1 stop15h 50mMultiple Airlines
Deal found 16/10C$ 534
Wed 5/1110:55 a.m.YYZ - ORF
1 stop6h 43mMultiple Airlines
Sat 8/116:02 p.m.ORF - YYZ
1 stop17h 41mMultiple Airlines
Deal found 15/10C$ 548

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 17 October 2025.

Round-trip from

C$ 420

One-way from

C$ 223

Popular in

August

Cheapest in

January

Average price

C$ 760
5/12-12/12
  • 5/12-12/12
  • 2 total stops
  • 37h 33m total
  • Toronto to Norfolk
Search Deals
27/11
  • 27/11
  • 1 total stop
  • 11h 23m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 189 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 17 October 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

Mon 15/12

2:20 p.m.-3:41 p.m.

1 stop25h 21m

Norfolk

Thu 18/12

5:15 p.m.-11:49 p.m.

1 stop6h 34m

C$ 451

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 7/11

10:15 a.m.-10:18 p.m.

1 stop12h 03m

Norfolk

Mon 10/11

4:57 p.m.-12:25 a.m.

1 stop7h 28m

C$ 489

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 5/12

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

1 stop7h 58m

Norfolk

Fri 12/12

10:05 p.m.-10:35 p.m.

2 stops24h 30m

C$ 493

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 15/11

10:15 a.m.-10:03 p.m.

1 stop11h 48m

Norfolk

Sat 22/11

5:15 p.m.-12:11 a.m.

1 stop6h 56m

C$ 522

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 5/11

10:55 a.m.-5:38 p.m.

1 stop6h 43m

Norfolk

Sat 8/11

6:02 p.m.-11:43 a.m.

1 stop17h 41m

C$ 548

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 2/11

7:10 a.m.-8:08 p.m.

1 stop12h 58m

Norfolk

Mon 3/11

1:19 p.m.-11:43 a.m.

2 stops22h 24m

C$ 562

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 5/11

12:15 p.m.-10:23 p.m.

2 stops10h 08m

Norfolk

Sat 8/11

7:04 a.m.-5:23 p.m.

1 stop10h 19m

C$ 591

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 4/11

10:55 a.m.-5:38 p.m.

1 stop6h 43m

C$ 343

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 5/11

7:15 a.m.-6:58 p.m.

3 stops11h 43m

C$ 372

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 26/10

10:20 a.m.-9:52 p.m.

1 stop11h 32m

C$ 388

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/10

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 3 hours 56 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 Sunday at noon, 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 WestJet, Air Canada and United Airlines.

WestJet
WestJet
From C$ 390
United Airlines
United Airlines
From C$ 355
Air Canada
Air Canada
From C$ 330
American Airlines
American Airlines
From C$ 286

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 17 October 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
8,982 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,982 reviews
United Airlines
7.4
Good
8,982 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
WestJet
7.2
Good
3,127 reviews
United Airlines
7.4
Good
8,982 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,306 reviews
United Airlines
7.4
Good
8,982 reviews
Check prices

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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, Toronto offers the quickest one-way flight (3 hours 56 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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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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