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Cheap flights from Winnipeg to Chesapeake from C$ 489

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — RIC
24 Nov — 1 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Winnipeg to Chesapeake

Enter your travel dates to find the best prices.

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 25 October 2025.

Fri 31/107:30 a.m.YWG - ORF
1 stop10h 07mDelta
Mon 3/116:17 p.m.ORF - YWG
2 stops18h 13mDelta
Deal found 23/10C$ 925
Fri 31/108:40 a.m.YWG - ORF
2 stops13h 58mUnited Airlines
Mon 3/118:05 p.m.ORF - YWG
2 stops16h 52mUnited Airlines
Deal found 23/10C$ 1,027
Fri 31/106:00 a.m.YWG - ORF
2 stops10h 30mAmerican Airlines
Mon 3/117:29 p.m.ORF - YWG
3 stops53h 06mAmerican Airlines
Deal found 23/10C$ 1,315

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 25 October 2025.

Round-trip from

C$ 489

Popular in

July

Cheapest in

October

Average price

C$ 595
United Airlines
  • United Airlines
  • 7/4-8/4
  • 2 total stops
  • 27h 13m total
  • Winnipeg to Chesapeake
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 122 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 25 October 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

Tue 7/4

8:30 a.m.-10:55 p.m.

1 stop13h 25m

Norfolk

Wed 8/4

8:00 a.m.-8:48 p.m.

1 stop13h 48m

C$ 489

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/10

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, February is the cheapest month in which you can book a flight from Winnipeg to Chesapeake (average of C$ 587). Flying from Winnipeg to Chesapeake in August is currently the most expensive (average of C$ 1,196). 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 25 October 2025.

It’s typically best to fly out from Winnipeg to Chesapeake in the afternoon. Doing so could potentially save you 9% on the flight price compared to flying in the evening, which is usually more expensive.

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 13h 25m. There are 2216 km between Winnipeg and Chesapeake.

  • 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, February is the cheapest month in which you can book a flight from Winnipeg to Chesapeake (average of C$ 587). Flying from Winnipeg to Chesapeake in August is currently the most expensive (average of C$ 1,196). 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

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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 25 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 818AverageC$ 870FlexibilityNo 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?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chesapeake from Winnipeg today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Chesapeake?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Chesapeake for you. Better yet — we are completely free to use.

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.

Can Cheapflights notify me if prices for flights from Winnipeg to Chesapeake become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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