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Cheap flights from Winnipeg to Chesapeake from C$ 351

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 25/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — RIC
15 Jun — 22 Jun1
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 16 May 2026.

Fri 18/912:40 p.m.
YWG
-
ORF
1 stop9h 54m
Delta
Mon 21/95:50 a.m.
ORF
-
YWG
2 stops15h 19m
Delta
Deal found 12/5C$ 560
Sun 31/59:05 p.m.
YWG
-
ORF
2 stops13h 28m
WestJet
Tue 2/64:58 p.m.
ORF
-
YWG
2 stops32h 57m
WestJet
Deal found 12/5C$ 579
Thu 28/55:41 p.m.
YWG
-
ORF
1 stop5h 11m
Delta
Tue 16/610:20 a.m.
ORF
-
YWG
2 stops14h 09m
Delta
Deal found 12/5C$ 595
Tue 9/67:00 a.m.
YWG
-
ORF
1 stop16h 57m
United Airlines
Tue 16/68:00 a.m.
ORF
-
YWG
1 stop15h 38m
United Airlines
Deal found 12/5C$ 610
Fri 18/97:00 a.m.
YWG
-
ORF
1 stop7h 13m
United Airlines
Mon 21/95:02 p.m.
ORF
-
YWG
1 stop6h 31m
United Airlines
Deal found 15/5C$ 621
Fri 18/96:15 a.m.
YWG
-
ORF
2 stops14h 17m
WestJet
Mon 21/95:30 a.m.
ORF
-
YWG
2 stops9h 55m
WestJet
Deal found 14/5C$ 624
Sun 31/59:05 p.m.
YWG
-
ORF
2 stops13h 28m
WestJet
Tue 16/62:44 p.m.
ORF
-
YWG
2 stops31h 56m
WestJet
Deal found 12/5C$ 630
Thu 28/56:15 a.m.
YWG
-
ORF
2 stops10h 06m
WestJet
Tue 16/610:20 a.m.
ORF
-
YWG
2 stops28h 45m
WestJet
Deal found 12/5C$ 643

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 16 May 2026.

Round-trip from

C$ 560

One-way from

C$ 351
Delta
  • Delta
  • 18/9-21/9
  • 3 total stops
  • 25h 13m total
  • Winnipeg to Chesapeake
Search Deals
WestJet
  • WestJet
  • 25/6
  • 2 total stops
  • 10h 02m 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 16 May 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 18/9

12:40 p.m.-11:34 p.m.

1 stop9h 54m

Norfolk

Mon 21/9

5:50 a.m.-8:09 p.m.

2 stops15h 19m

C$ 560
Quickest round-trip

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 28/5

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

1 stop5h 11m

Norfolk

Tue 16/6

10:20 a.m.-11:29 p.m.

2 stops14h 09m

C$ 595

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Tue 9/6

7:00 a.m.-12:57 a.m.

1 stop16h 57m

Norfolk

Tue 16/6

8:00 a.m.-10:38 p.m.

1 stop15h 38m

C$ 610

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 18/9

8:45 a.m.-11:25 p.m.

1 stop13h 40m

Norfolk

Mon 21/9

5:02 p.m.-10:33 p.m.

1 stop6h 31m

C$ 623

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Fri 18/9

6:15 a.m.-9:32 p.m.

2 stops14h 17m

Norfolk

Mon 21/9

5:30 a.m.-2:25 p.m.

2 stops9h 55m

C$ 624
Cheapest one-way

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 25/6

6:15 a.m.-5:17 p.m.

2 stops10h 02m

C$ 351

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 25/6

6:00 a.m.-11:26 a.m.

3 stops28h 26m

C$ 400
Quickest one-way

WinnipegNorfolk

YWG - ORF

YWGORF

Winnipeg

Thu 25/6

7:00 a.m.-3:43 p.m.

1 stop7h 43m

C$ 440

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

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.

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 16 May 2026.
See what other customers who have flown with WestJet 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.
WestJet
7.2
Good
3,336 reviews
Check prices

Food

6.2

Boarding

7.4

Crew

7.9

Comfort

7.0

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,336 reviews
WestJet
7.2
Good
3,336 reviews
Check prices

Food

6.2

Boarding

7.4

Crew

7.9

Comfort

7.0

Overall

7.2

Entertainment

6.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

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 54m. 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 Reagan-National flights
Winnipeg to Dulles Intl 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 16 May 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 575AverageC$ 609FlexibilityNo cancel feeOn-time60%
Search WestJet 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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