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C$ 245+ 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 24/5. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
13 May — 20 May1
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 13 April 2026.

Tue 16/69:50 a.m.
YYZ
-
ORF
1 stop10h 50m
Multiple Airlines
Sun 21/69:35 p.m.
ORF
-
YYZ
1 stop22h 30m
Multiple Airlines
Deal found 9/4C$ 425
Sun 24/56:30 a.m.
YYZ
-
ORF
1 stop11h 09m
Multiple Airlines
Sat 30/59:12 p.m.
ORF
-
YYZ
1 stop26h 23m
Multiple Airlines
Deal found 9/4C$ 426
Sat 23/51:30 p.m.
YYZ
-
ORF
1 stop28h 09m
Multiple Airlines
Sat 30/59:12 p.m.
ORF
-
YYZ
1 stop26h 23m
Multiple Airlines
Deal found 8/4C$ 437
Mon 25/58:10 a.m.
YYZ
-
ORF
2 stops51h 01m
Multiple Airlines
Mon 1/69:12 p.m.
ORF
-
YYZ
1 stop19h 33m
Multiple Airlines
Deal found 10/4C$ 540
Sun 17/57:30 a.m.
YYZ
-
ORF
1 stop10h 09m
Multiple Airlines
Wed 20/512:06 p.m.
ORF
-
YYZ
2 stops28h 49m
Multiple Airlines
Deal found 11/4C$ 555
Tue 18/87:45 a.m.
YYZ
-
ORF
1 stop13h 16m
Multiple Airlines
Sat 29/812:00 p.m.
ORF
-
YYZ
2 stops23h 35m
Multiple Airlines
Deal found 9/4C$ 597
Sat 25/42:20 p.m.
YYZ
-
ORF
1 stop7h 16m
Multiple Airlines
Sun 26/48:57 p.m.
ORF
-
YYZ
1 stop17h 08m
Multiple Airlines
Deal found 9/4C$ 599
Sun 26/46:30 a.m.
YYZ
-
ORF
2 stops34h 34m
Multiple Airlines
Thu 30/48:57 p.m.
ORF
-
YYZ
1 stop14h 48m
Multiple Airlines
Deal found 11/4C$ 602

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 13 April 2026.

Round-trip from

C$ 425

One-way from

C$ 245

Popular in

August

Cheapest in

December

Average price

C$ 653
16/6-21/6
  • 16/6-21/6
  • 2 total stops
  • 33h 20m total
  • Toronto to Norfolk
Search Deals
24/5
  • 24/5
  • 1 total stop
  • 11h 09m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 13 April 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 16/6

9:50 a.m.-8:40 p.m.

1 stop10h 50m

Norfolk

Sun 21/6

9:35 p.m.-8:05 p.m.

1 stop22h 30m

C$ 425

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 26/4

6:30 a.m.-5:04 p.m.

2 stops34h 34m

Norfolk

Thu 30/4

8:57 p.m.-11:45 a.m.

1 stop14h 48m

C$ 602

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 23/5

10:00 a.m.-6:04 p.m.

1 stop8h 04m

Norfolk

Wed 27/5

10:25 a.m.-9:19 p.m.

1 stop10h 54m

C$ 626

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 22/5

3:45 p.m.-11:44 p.m.

1 stop7h 59m

Norfolk

Sun 24/5

5:04 a.m.-11:12 a.m.

1 stop6h 08m

C$ 627

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 8/7

6:00 a.m.-6:29 p.m.

1 stop12h 29m

Norfolk

Mon 13/7

10:31 a.m.-11:44 p.m.

1 stop13h 13m

C$ 634
Quickest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 10/5

7:30 a.m.-12:04 p.m.

1 stop4h 34m

Norfolk

Sat 16/5

10:37 a.m.-2:19 p.m.

1 stop3h 42m

C$ 651

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 8/6

3:00 p.m.-11:44 p.m.

2 stops8h 44m

Norfolk

Sun 14/6

8:00 a.m.-3:46 p.m.

1 stop7h 46m

C$ 659

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 22/5

9:49 a.m.-4:02 p.m.

1 stop6h 13m

Norfolk

Sun 24/5

7:08 a.m.-11:15 a.m.

1 stop4h 07m

C$ 669

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 14/6

5:15 p.m.-12:41 a.m.

1 stop7h 26m

Norfolk

Sun 28/6

6:00 a.m.-11:49 a.m.

1 stop5h 49m

C$ 669
Cheapest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Wed 27/5

9:50 a.m.-11:11 a.m.

2 stops25h 21m

C$ 285

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 16 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 5 hours 18 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, Air Canada and WestJet.

WestJet
WestJet
From C$ 347
United Airlines
United Airlines
From C$ 402
Air Canada
Air Canada
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 WestJet.

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 13 April 2026.
Get a feel of what it's like to fly with United Airlines and WestJet 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
9,581 reviews
Check prices

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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
9,581 reviews
United Airlines
7.4
Good
9,581 reviews
Check prices

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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
WestJet
7.2
Good
3,320 reviews
United Airlines
7.4
Good
9,581 reviews
Check prices

Comfort

7.3

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

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 (4 hours 14 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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