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Cheap flights from Winnipeg to Chesapeake from C$ 279

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 30/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — RIC
9 Mar — 16 Mar1
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 7 February 2026.

Mon 2/311:53 a.m.
YWG
-
ORF
2 stops9h 28m
Delta
Wed 4/36:35 a.m.
ORF
-
YWG
1 stop9h 34m
Delta
Deal found 2/2C$ 554
Mon 2/35:00 a.m.
YWG
-
ORF
2 stops17h 00m
WestJet
Wed 4/312:37 p.m.
ORF
-
YWG
2 stops13h 03m
WestJet
Deal found 3/2C$ 588
Sun 8/32:20 p.m.
YWG
-
ORF
1 stop5h 34m
United Airlines
Sun 22/36:15 a.m.
ORF
-
YWG
1 stop6h 42m
United Airlines
Deal found 6/2C$ 602
Sun 8/37:20 p.m.
YWG
-
ORF
2 stops18h 12m
Air Canada
Sun 22/36:15 a.m.
ORF
-
YWG
1 stop6h 42m
Air Canada
Deal found 6/2C$ 613
Sun 8/35:00 a.m.
YWG
-
ORF
2 stops18h 24m
WestJet
Sun 22/35:50 a.m.
ORF
-
YWG
2 stops29h 17m
WestJet
Deal found 6/2C$ 652
Sun 8/35:00 a.m.
YWG
-
ORF
3 stops36h 26m
Multiple Airlines
Sun 22/36:45 a.m.
ORF
-
YWG
2 stops30h 22m
Multiple Airlines
Deal found 6/2C$ 928

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 7 February 2026.

Round-trip from

C$ 554

One-way from

C$ 279
Delta
  • Delta
  • 2/3-4/3
  • 3 total stops
  • 19h 02m total
  • Winnipeg to Chesapeake
Search Deals
United Airlines
  • United Airlines
  • 30/5
  • 1 total stop
  • 7h 14m 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 7 February 2026.
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

Mon 2/3

11:53 a.m.-10:21 p.m.

2 stops9h 28m

Norfolk

Wed 4/3

6:35 a.m.-3:09 p.m.

1 stop9h 34m

C$ 554

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Mon 2/3

5:00 a.m.-11:13 p.m.

2 stops17h 13m

Norfolk

Wed 4/3

12:37 p.m.-12:40 a.m.

2 stops13h 03m

C$ 555

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sun 8/3

2:20 p.m.-8:54 p.m.

1 stop5h 34m

Norfolk

Sun 22/3

6:15 a.m.-11:57 a.m.

1 stop6h 42m

C$ 602

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sun 8/3

7:20 p.m.-2:32 p.m.

2 stops18h 12m

Norfolk

Sun 22/3

6:15 a.m.-11:57 a.m.

1 stop6h 42m

C$ 613

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sun 8/3

5:00 a.m.-12:24 a.m.

2 stops18h 24m

Norfolk

Sun 22/3

5:50 a.m.-10:07 a.m.

2 stops29h 17m

C$ 652

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sat 30/5

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

1 stop7h 14m

C$ 279

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Sun 22/3

7:30 a.m.-11:38 a.m.

1 stop27h 08m

C$ 297

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

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.

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 7 February 2026.
See what other customers who have flown with United Airlines from Winnipeg to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,244 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,244 reviews
United Airlines
7.4
Good
9,244 reviews
Check prices

Comfort

7.3

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 9h 28m. 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.

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 7 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 581AverageC$ 826FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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