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Cheap flights from Winnipeg to Chesapeake from C$ 361

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — RIC
27 Apr — 4 May1
1 adult
1 adult, Economy, 0 bags

Cheap 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 28 March 2026.

Fri 29/57:00 a.m.
YWG
-
ORF
1 stop7h 14m
United Airlines
Tue 2/67:59 p.m.
ORF
-
YWG
2 stops16h 53m
United Airlines
Deal found 27/3C$ 427
Tue 28/46:15 a.m.
YWG
-
ORF
2 stops15h 40m
WestJet
Thu 30/45:45 a.m.
ORF
-
YWG
2 stops20h 10m
WestJet
Deal found 23/3C$ 562
Fri 29/56:15 a.m.
YWG
-
ORF
2 stops8h 47m
WestJet
Tue 2/65:20 a.m.
ORF
-
YWG
2 stops10h 05m
WestJet
Deal found 26/3C$ 568
Tue 28/45:20 p.m.
YWG
-
ORF
1 stop5h 20m
Delta
Thu 30/411:10 a.m.
ORF
-
YWG
2 stops13h 20m
Delta
Deal found 23/3C$ 585
Fri 29/56:00 a.m.
YWG
-
ORF
2 stops16h 15m
WestJet
Sun 31/55:20 a.m.
ORF
-
YWG
2 stops10h 05m
WestJet
Deal found 24/3C$ 599

Find flight deals from Winnipeg to Chesapeake

Keep the following information in mind while searching for Winnipeg to Chesapeake flight deals. Data was last updated 28 March 2026.

Round-trip from

C$ 427

One-way from

C$ 361
United Airlines
  • United Airlines
  • 29/5-2/6
  • 2 total stops
  • 14h 06m total
  • Winnipeg to Chesapeake
Search Deals
Delta
  • Delta
  • 7/4
  • 2 total stops
  • 9h 35m total
  • Winnipeg to Chesapeake
Search Deals

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 28 March 2026.
Use the filters below to find and compare flights from Winnipeg to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 29/5

7:00 a.m.-3:14 p.m.

1 stop7h 14m

Norfolk

Tue 2/6

7:59 p.m.-11:52 a.m.

2 stops16h 53m

C$ 427

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Tue 28/4

6:15 a.m.-10:55 p.m.

2 stops15h 40m

Norfolk

Thu 30/4

5:45 a.m.-12:55 a.m.

2 stops20h 10m

C$ 562
Quickest round-trip

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 29/5

6:15 a.m.-4:02 p.m.

2 stops8h 47m

Norfolk

Tue 2/6

5:20 a.m.-2:25 p.m.

2 stops10h 05m

C$ 568

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 29/5

7:00 a.m.-3:14 p.m.

1 stop7h 14m

Norfolk

Sun 31/5

4:57 p.m.-8:57 p.m.

2 stops29h 00m

C$ 616
Cheapest one-way

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Tue 7/4

11:55 a.m.-10:30 p.m.

2 stops9h 35m

C$ 361

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 14/5

6:00 a.m.-11:15 p.m.

2 stops16h 15m

C$ 377
Quickest one-way

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 14/5

5:41 p.m.-11:52 p.m.

1 stop5h 11m

C$ 403

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 14/5

10:30 p.m.-11:15 a.m.

3 stops35h 45m

C$ 406

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/3

Sorted by cheapest first

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
No data available for this route at this time. Please check back soon.

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. 0 airlines have 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 7h 14m. 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.

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

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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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