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C$ 248+ 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 17/5. Fares are subject to change and may not be available on all flights or dates of travel.
— RIC
22 May — 29 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 22 April 2026.

Thu 28/57:45 a.m.
YYZ
-
ORF
1 stop12h 32m
Multiple Airlines
Thu 4/69:12 p.m.
ORF
-
YYZ
1 stop26h 23m
Multiple Airlines
Deal found 17/4C$ 397
Sun 24/56:30 a.m.
YYZ
-
ORF
1 stop11h 09m
Multiple Airlines
Sun 31/56:34 p.m.
ORF
-
YYZ
2 stops25h 10m
Multiple Airlines
Deal found 20/4C$ 470
Wed 27/57:45 a.m.
YYZ
-
ORF
2 stops27h 26m
Multiple Airlines
Wed 3/69:06 a.m.
ORF
-
YYZ
1 stop10h 59m
Multiple Airlines
Deal found 18/4C$ 479
Wed 27/57:45 a.m.
YYZ
-
ORF
1 stop14h 00m
Multiple Airlines
Tue 2/612:06 p.m.
ORF
-
YYZ
2 stops31h 59m
Multiple Airlines
Deal found 18/4C$ 483
Mon 11/59:30 a.m.
YYZ
-
ORF
1 stop8h 09m
Multiple Airlines
Fri 15/56:34 p.m.
ORF
-
YYZ
1 stop19h 31m
Multiple Airlines
Deal found 19/4C$ 496
Fri 5/68:10 a.m.
YYZ
-
ORF
1 stop14h 38m
Multiple Airlines
Fri 12/612:21 p.m.
ORF
-
YYZ
2 stops25h 44m
Multiple Airlines
Deal found 20/4C$ 508
Thu 2/76:30 a.m.
YYZ
-
ORF
1 stop26h 38m
Multiple Airlines
Mon 6/710:09 a.m.
ORF
-
YYZ
1 stop10h 46m
Multiple Airlines
Deal found 20/4C$ 512

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 April 2026.

Round-trip from

C$ 397

One-way from

C$ 248

Popular in

August

Cheapest in

December

Average price

C$ 644
28/5-4/6
  • 28/5-4/6
  • 2 total stops
  • 38h 55m total
  • Toronto to Norfolk
Search Deals
17/5
  • 17/5
  • 1 total stop
  • 10h 09m total
  • Toronto to Chesapeake
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 19 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 22 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 26/5

11:01 a.m.-9:53 p.m.

1 stop10h 52m

Norfolk

Tue 2/6

5:17 a.m.-4:48 p.m.

1 stop11h 31m

C$ 609

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.-5:55 p.m.

1 stop7h 30m

C$ 614

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Tue 26/5

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

2 stops8h 44m

Norfolk

Tue 2/6

6:00 a.m.-1:42 p.m.

1 stop7h 42m

C$ 617

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

10:25 a.m.-4:12 p.m.

1 stop5h 47m

C$ 617

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 17/5

10:15 a.m.-5:19 p.m.

1 stop7h 04m

Norfolk

Sun 24/5

6:05 a.m.-10:04 a.m.

1 stop3h 59m

C$ 617

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sat 23/5

6:12 p.m.-11:20 p.m.

1 stop5h 08m

Norfolk

Tue 26/5

5:27 p.m.-11:16 p.m.

1 stop5h 49m

C$ 617

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Fri 22/5

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

2 stops8h 44m

Norfolk

Sun 24/5

6:05 a.m.-10:04 a.m.

1 stop3h 59m

C$ 632
Quickest round-trip

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 14/6

10:15 a.m.-3:43 p.m.

1 stop5h 28m

Norfolk

Sun 28/6

6:05 a.m.-10:04 a.m.

1 stop3h 59m

C$ 642
Cheapest one-way

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Sun 17/5

8:00 p.m.-11:11 a.m.

2 stops39h 11m

C$ 251

TorontoNorfolk

YYZ - ORF

YYZORF

Toronto Pearson Intl

Thu 4/6

4:15 p.m.-11:11 a.m.

2 stops18h 56m

C$ 266

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/4

Showing 1-10 of 17 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$ 342
United Airlines
United Airlines
From C$ 396
Air Canada
Air Canada
From C$ 395

What are the cheapest airlines that fly to Chesapeake?

The cheapest airlines flying from Toronto to Chesapeake are Air Canada, WestJet 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 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
9,625 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,625 reviews
United Airlines
7.4
Good
9,625 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
WestJet
7.2
Good
3,324 reviews
United Airlines
7.4
Good
9,625 reviews
Check prices

Comfort

7.3

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 39 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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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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