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Cheap flights from Winnipeg to Chesapeake from C$ 826

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — RIC
25 Aug — 1 Sep1
1 adult

Cheap flight deals from Winnipeg to Chesapeake

Keep the following information in mind while searching for Winnipeg to Chesapeake flight deals. Data was last updated 20 August 2025.

Round-trip from

C$ 826

Popular in

July

Cheapest in

October
WestJet
  • WestJet
  • 10/10-20/10
  • 4 total stops
  • 40h 31m total
  • Winnipeg to Chesapeake
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease (C$ 11 potential savings vs. average RT price).
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Find flight deals from Winnipeg to Chesapeake

Cheapest flights from Winnipeg to Chesapeake
Explore the most affordable flight options available from Winnipeg to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 20 August 2025.

Fri 10/106:30 a.m.YWG - ORF
2 stops28h 37mWestJet
Mon 20/101:36 p.m.ORF - YWG
2 stops11h 54mWestJet
Deal found 20/8C$ 826
Fri 10/109:00 a.m.YWG - ORF
1 stop14h 20mDelta
Mon 20/106:46 p.m.ORF - YWG
1 stop5h 41mDelta
Deal found 19/8C$ 851
Fri 10/102:20 p.m.YWG - ORF
1 stop6h 18mUnited Airlines
Mon 20/104:56 p.m.ORF - YWG
1 stop6h 37mUnited Airlines
Deal found 20/8C$ 870
Sat 13/96:40 a.m.YWG - ORF
2 stops11h 02mDelta
Wed 17/910:13 a.m.ORF - YWG
2 stops10h 58mDelta
Deal found 18/8C$ 883
Sat 13/97:00 a.m.YWG - ORF
1 stop6h 40mUnited Airlines
Wed 17/96:30 a.m.ORF - YWG
1 stop17h 03mUnited Airlines
Deal found 18/8C$ 924

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Chesapeake that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 20 August 2025.
Use the filters below to find and compare flights from Winnipeg to Chesapeake that are best for you.

Fly from

Winnipeg

Fly to

Chesapeake

Route

Depart

Return

Price

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 10/10

6:30 a.m.-12:07 p.m.

2 stops28h 37m

Norfolk

Mon 20/10

1:36 p.m.-12:30 a.m.

2 stops11h 54m

C$ 826

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 10/10

9:00 a.m.-12:20 a.m.

1 stop14h 20m

Norfolk

Mon 20/10

6:46 p.m.-11:27 p.m.

1 stop5h 41m

C$ 851

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 10/10

2:20 p.m.-9:38 p.m.

1 stop6h 18m

Norfolk

Mon 20/10

4:56 p.m.-10:33 p.m.

1 stop6h 37m

C$ 870

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sat 13/9

6:40 a.m.-6:42 p.m.

2 stops11h 02m

Norfolk

Wed 17/9

6:55 p.m.-11:27 p.m.

1 stop5h 32m

C$ 899

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sat 13/9

7:00 a.m.-2:40 p.m.

1 stop6h 40m

Norfolk

Wed 17/9

6:30 a.m.-10:33 p.m.

1 stop17h 03m

C$ 924

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/8

Best time to book a flight from Winnipeg to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Winnipeg 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 from Winnipeg to Chesapeake

What is the cheapest month to book a flight from Winnipeg to Chesapeake?

Currently, October is the cheapest month in which you can book a flight from Winnipeg to Chesapeake (average of C$ 274). Flying from Winnipeg to Chesapeake in March is currently the most expensive (average of C$ 460). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to C6E?

Find hourly flight availability from Winnipeg to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 20 August 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Chesapeake as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Chesapeake. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Chesapeake?

    For a flight from Winnipeg to Chesapeake, you will be flying from Winnipeg. Winnipeg (YWG) is just 7.3 km from the centre of the city. Winnipeg is the only Winnipeg airport and it handles 0 outbound flights to Chesapeake per day. 1 airline has flights to Chesapeake from Winnipeg on a regular basis.

  • How long is the flight from Winnipeg to Chesapeake?

    Departing from Winnipeg to Chesapeake will take you 14h 20m. There are 2216 km between Winnipeg and Chesapeake. This flight may include one or multiple stops.

  • Can I find deals for flights from Winnipeg to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Chesapeake.

  • Can I find deals for business class flights from Winnipeg to Chesapeake?

    Yes. Cheapflights offers flight deals from Winnipeg to Chesapeake by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Chesapeake?

    Currently, October is the cheapest month in which you can book a flight from Winnipeg to Chesapeake (average of C$ 274). Flying from Winnipeg to Chesapeake in March is currently the most expensive (average of C$ 460). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Winnipeg to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Dulles Intl flights
Winnipeg to Reagan-National flights
Winnipeg to Norfolk flights

Top airline flying from Winnipeg to Chesapeake

Discover the top airline that operate flights from Winnipeg to Chesapeake. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 20 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 808AverageC$ 859FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Chesapeake?

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Can Cheapflights find flights from Winnipeg to Chesapeake with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Winnipeg to Chesapeake flexibly with Cheapflights today.

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