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C$ 300+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
21 Aug — 28 Aug1
1 adult
1 adult, Economy, 0 bags

Flights to Chesapeake in 2026

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 22 July 2026.

Tue 8/96:10 p.m.
YYZ
-
ORF
1 stop5h 23m
Delta
Tue 15/96:00 a.m.
ORF
-
YYZ
1 stop5h 18m
Delta
Deal found 17/7C$ 532
Sat 22/82:15 p.m.
YYZ
-
ORF
1 stop6h 55m
American Airlines
Sat 29/86:00 a.m.
ORF
-
YYZ
1 stop7h 26m
American Airlines
Deal found 19/7C$ 535
Mon 5/109:50 a.m.
YYZ
-
ORF
1 stop27h 23m
Multiple Airlines
Thu 15/1012:57 p.m.
ORF
-
YYZ
2 stops27h 58m
Multiple Airlines
Deal found 18/7C$ 538
Tue 10/117:15 a.m.
YYZ
-
ORF
1 stop10h 00m
Multiple Airlines
Mon 16/116:00 a.m.
ORF
-
YYZ
1 stop18h 10m
Multiple Airlines
Deal found 20/7C$ 542
Thu 27/86:14 p.m.
YYZ
-
ORF
1 stop5h 28m
Delta
Tue 1/92:42 p.m.
ORF
-
YYZ
1 stop6h 37m
Delta
Deal found 18/7C$ 551
Sun 18/108:10 a.m.
YYZ
-
ORF
2 stops27h 52m
Multiple Airlines
Sat 24/103:16 p.m.
ORF
-
YYZ
1 stop23h 42m
Multiple Airlines
Deal found 18/7C$ 555
Thu 24/99:50 a.m.
YYZ
-
ORF
1 stop7h 25m
Multiple Airlines
Thu 1/107:30 a.m.
ORF
-
YYZ
2 stops13h 25m
Multiple Airlines
Deal found 20/7C$ 569
Thu 8/105:29 p.m.
YYZ
-
ORF
1 stop4h 31m
American Airlines
Mon 12/106:00 a.m.
ORF
-
YYZ
1 stop4h 17m
American Airlines
Deal found 19/7C$ 572
Mon 17/85:25 p.m.
YYZ
-
ORF
1 stop4h 23m
American Airlines
Mon 24/86:00 a.m.
ORF
-
YYZ
1 stop7h 26m
American Airlines
Deal found 20/7C$ 579
Thu 24/96:00 a.m.
YYZ
-
ORF
1 stop7h 59m
American Airlines
Thu 1/103:45 p.m.
ORF
-
YYZ
1 stop6h 54m
American Airlines
Deal found 20/7C$ 580

Find flight deals to Chesapeake

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 22 July 2026.

Round-trip from

C$ 532

One-way from

C$ 300

Popular in

August

Cheapest in

May

Average price

C$ 759
Delta
  • Delta
  • 8/9-15/9
  • 2 total stops
  • 10h 41m total
  • Toronto to Norfolk
Search Deals
11/11
  • 11/11
  • 2 total stops
  • 24h 47m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 122 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 22 July 2026.
Use the filters below to find and compare flights to Chesapeake that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 8/9

6:10 p.m.-11:33 p.m.

1 stop5h 23m

Norfolk

Tue 15/9

6:00 a.m.-11:18 a.m.

1 stop5h 18m

C$ 532
Quickest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 9/9

6:10 a.m.-11:26 a.m.

1 stop5h 16m

Norfolk

Sat 12/9

6:00 a.m.-11:18 a.m.

1 stop5h 18m

C$ 532

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 6/10

7:55 a.m.-1:45 p.m.

1 stop5h 50m

Norfolk

Tue 13/10

6:30 p.m.-11:37 p.m.

1 stop5h 07m

C$ 534

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 27/8

6:14 p.m.-11:42 p.m.

1 stop5h 28m

Norfolk

Tue 1/9

2:42 p.m.-9:19 p.m.

1 stop6h 37m

C$ 551

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 6/10

12:10 p.m.-4:22 p.m.

1 stop4h 12m

Norfolk

Tue 13/10

5:30 a.m.-6:55 p.m.

2 stops13h 25m

C$ 592

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 21/8

2:24 p.m.-11:42 p.m.

1 stop9h 18m

Norfolk

Sun 23/8

5:23 a.m.-10:25 a.m.

1 stop5h 02m

C$ 617
Cheapest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 11/11

11:15 a.m.-12:02 p.m.

2 stops24h 47m

C$ 300

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 12/8

6:00 a.m.-11:25 a.m.

1 stop5h 25m

C$ 307
Quickest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 5/8

6:00 a.m.-11:01 a.m.

1 stop5h 01m

C$ 308

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 14/8

4:10 p.m.-11:42 p.m.

1 stop7h 32m

C$ 324

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/7

Showing 1-10 of 15 resultsSorted by cheapest first
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 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.

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 American Airlines.

United Airlines
United Airlines
From C$ 442
WestJet
WestJet
From C$ 589
Air Canada
Air Canada
From C$ 417
American Airlines
American Airlines
From C$ 589

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are Air Canada, American Airlines 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 22 July 2026.
Get a feel of what it's like to fly with United Airlines 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
10,020 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
10,020 reviews
United Airlines
7.4
Good
10,020 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.7

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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, Ottawa offers the quickest one-way flight (3 hours 42 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.

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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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