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C$ 288+ 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 17/8. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
3 Jul — 10 Jul1
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 3 June 2026.

Mon 15/65:15 p.m.
YYZ
-
ORF
1 stop7h 42m
United Airlines
Tue 23/65:50 a.m.
ORF
-
YYZ
1 stop5h 53m
United Airlines
Deal found 29/5C$ 620
Mon 28/96:10 p.m.
YYZ
-
ORF
1 stop5h 23m
Delta
Wed 30/92:24 p.m.
ORF
-
YYZ
1 stop6h 53m
Delta
Deal found 30/5C$ 621
Wed 15/712:45 p.m.
YYZ
-
ORF
1 stop9h 19m
American Airlines
Fri 24/76:11 p.m.
ORF
-
YYZ
1 stop5h 02m
American Airlines
Deal found 1/6C$ 632
Wed 15/76:15 a.m.
YYZ
-
ORF
1 stop5h 42m
American Airlines
Fri 17/76:11 p.m.
ORF
-
YYZ
1 stop5h 02m
American Airlines
Deal found 2/6C$ 642
Sat 20/62:00 p.m.
YYZ
-
ORF
1 stop7h 36m
Air Canada
Sat 27/65:00 p.m.
ORF
-
YYZ
1 stop6h 59m
Air Canada
Deal found 28/5C$ 660
Fri 10/74:10 p.m.
YYZ
-
ORF
1 stop7h 22m
Delta
Fri 24/76:05 a.m.
ORF
-
YYZ
1 stop7h 29m
Delta
Deal found 29/5C$ 675
Thu 8/106:08 p.m.
YYZ
-
ORF
1 stop5h 18m
Delta
Mon 12/105:50 a.m.
ORF
-
YYZ
1 stop7h 35m
Delta
Deal found 30/5C$ 677
Fri 29/57:45 a.m.
YYZ
-
ORF
1 stop14h 53m
Multiple Airlines
Fri 5/69:12 p.m.
ORF
-
YYZ
2 stops23h 12m
Multiple Airlines
Deal found 28/5C$ 684
Wed 23/1210:58 a.m.
YYZ
-
ORF
1 stop12h 03m
American Airlines
Sun 27/126:00 a.m.
ORF
-
YYZ
1 stop10h 39m
American Airlines
Deal found 31/5C$ 685
Sun 12/711:40 a.m.
YYZ
-
ORF
1 stop10h 02m
Delta
Tue 4/82:42 p.m.
ORF
-
YYZ
1 stop6h 37m
Delta
Deal found 28/5C$ 688
Sat 27/66:15 a.m.
YYZ
-
ORF
1 stop6h 37m
Delta
Sat 4/710:45 a.m.
ORF
-
YYZ
1 stop7h 30m
Delta
Deal found 1/6C$ 689

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 3 June 2026.

Round-trip from

C$ 620

One-way from

C$ 288

Popular in

July

Cheapest in

September

Average price

C$ 847
United Airlines
  • United Airlines
  • 15/6-23/6
  • 2 total stops
  • 13h 35m total
  • Toronto to Norfolk
Search Deals
17/8
  • 17/8
  • 1 total stop
  • 14h 58m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 3 June 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

Sat 22/8

8:50 a.m.-9:41 p.m.

1 stop12h 51m

Norfolk

Sun 30/8

5:02 p.m.-12:13 a.m.

1 stop7h 11m

C$ 621
Quickest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 28/9

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

1 stop5h 23m

Norfolk

Wed 30/9

2:24 p.m.-9:17 p.m.

1 stop6h 53m

C$ 621

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 24/7

12:45 p.m.-10:04 p.m.

1 stop9h 19m

Norfolk

Mon 27/7

6:00 a.m.-10:16 a.m.

1 stop4h 16m

C$ 632

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 10/7

4:10 p.m.-11:32 p.m.

1 stop7h 22m

Norfolk

Fri 24/7

6:05 a.m.-1:34 p.m.

1 stop7h 29m

C$ 675

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 8/10

3:59 p.m.-11:26 p.m.

1 stop7h 27m

Norfolk

Mon 12/10

5:29 p.m.-10:51 p.m.

1 stop5h 22m

C$ 675

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 28/9

7:30 a.m.-11:43 p.m.

2 stops16h 13m

Norfolk

Wed 30/9

6:15 a.m.-10:04 a.m.

1 stop3h 49m

C$ 678

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 7/7

4:05 p.m.-11:44 p.m.

2 stops7h 39m

Norfolk

Wed 15/7

6:05 a.m.-1:08 p.m.

2 stops7h 03m

C$ 706

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 16/7

8:45 a.m.-3:50 p.m.

1 stop7h 05m

Norfolk

Thu 23/7

6:05 a.m.-1:08 p.m.

2 stops7h 03m

C$ 706
Cheapest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 7/7

6:30 a.m.-5:32 p.m.

2 stops11h 02m

C$ 321

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Mon 17/8

9:30 a.m.-1:30 p.m.

2 stops28h 00m

C$ 329

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 20 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 WestJet.

United Airlines
United Airlines
From C$ 434
WestJet
WestJet
From C$ 579
Air Canada
Air Canada
From C$ 410

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 3 June 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
9,777 reviews
Check prices

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,777 reviews
United Airlines
7.4
Good
9,777 reviews
Check prices

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
WestJet
7.2
Good
3,350 reviews
United Airlines
7.4
Good
9,777 reviews
Check prices

Food

6.6

Comfort

7.3

Crew

8.1

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 45 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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