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Cheap flights from Winnipeg to Maryland from C$ 169

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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BWI
27 Jan — 3 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Maryland

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Maryland
Explore the most affordable flight options available from Winnipeg to Maryland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 December 2025.

Mon 29/125:45 p.m.YWG - IAD
1 stop5h 12mWestJet
Wed 7/19:00 a.m.IAD - YWG
1 stop7h 07mWestJet
Deal found 27/12C$ 955
Wed 31/128:00 a.m.YWG - PHL
1 stop10h 22mMultiple Airlines
Tue 6/18:54 p.m.PHL - YWG
2 stops39h 41mMultiple Airlines
Deal found 27/12C$ 969
Wed 31/1212:35 p.m.YWG - PHL
1 stop8h 36mDelta
Tue 6/16:15 a.m.PHL - YWG
1 stop5h 48mDelta
Deal found 27/12C$ 983
Wed 31/122:20 p.m.YWG - PHL
2 stops8h 10mUnited Airlines
Tue 6/16:30 a.m.PHL - YWG
2 stops11h 49mUnited Airlines
Deal found 27/12C$ 991
Mon 29/128:00 a.m.YWG - BWI
1 stop10h 08mMultiple Airlines
Wed 7/19:09 p.m.BWI - YWG
2 stops39h 26mMultiple Airlines
Deal found 27/12C$ 1,203
Thu 25/129:45 a.m.YWG - IAD
1 stop5h 28mAir Canada
Fri 2/16:30 a.m.IAD - YWG
1 stop6h 27mAir Canada
Deal found 25/12C$ 1,263
Thu 25/121:30 p.m.YWG - DCA
1 stop8h 05mAir Canada
Fri 2/16:59 a.m.DCA - YWG
1 stop6h 20mAir Canada
Deal found 25/12C$ 1,281
Mon 29/125:45 p.m.YWG - BWI
1 stop4h 47mDelta
Wed 7/16:05 a.m.BWI - YWG
1 stop5h 58mDelta
Deal found 27/12C$ 1,283
Thu 25/1212:35 p.m.YWG - IAD
1 stop8h 38mDelta
Fri 2/16:00 a.m.IAD - YWG
1 stop6h 45mDelta
Deal found 25/12C$ 1,331
Thu 25/1212:35 p.m.YWG - DCA
2 stops9h 21mDelta
Fri 2/16:00 a.m.DCA - YWG
2 stops10h 07mDelta
Deal found 25/12C$ 1,547

Find flight deals from Winnipeg to Maryland

Keep the following information in mind while searching for Winnipeg to Maryland flight deals. Data was last updated 28 December 2025.

Round-trip from

C$ 291

One-way from

C$ 169

Popular in

November

Cheapest in

October

Average price

C$ 544
24/1-31/1
  • 24/1-31/1
  • 3 total stops
  • 47h 03m total
  • Winnipeg to Maryland
Search Deals
8/2
  • 8/2
  • 1 total stop
  • 8h 03m total
  • Winnipeg to Maryland
Search Deals
High demand for flights, 16% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Maryland 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 December 2025.
Use the filters below to find and compare flights from Winnipeg to Maryland that are best for you.

Fly from

Winnipeg

Fly to

Maryland

Route

Depart

Return

Price

WinnipegWashington, D.C.

YWG - IAD

YWGIAD

Winnipeg

Sat 24/1

9:00 p.m.-4:33 p.m.

2 stops18h 33m

Washington, D.C. Dulles Intl

Sat 31/1

11:39 a.m.-3:09 p.m.

1 stop28h 30m

C$ 291

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Sun 1/3

7:30 a.m.-12:57 a.m.

1 stop16h 27m

Philadelphia

Thu 5/3

5:30 a.m.-12:40 a.m.

2 stops20h 10m

C$ 354

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Sun 11/1

5:00 a.m.-8:47 a.m.

2 stops26h 47m

Philadelphia

Tue 13/1

7:12 p.m.-3:07 p.m.

1 stop20h 55m

C$ 380

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Sun 5/4

7:30 a.m.-12:51 a.m.

1 stop16h 21m

Philadelphia

Thu 9/4

1:00 p.m.-7:09 p.m.

2 stops31h 09m

C$ 395

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Fri 6/3

2:40 p.m.-10:59 a.m.

2 stops19h 19m

Philadelphia

Sun 8/3

5:05 a.m.-3:09 p.m.

1 stop11h 04m

C$ 406

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Fri 1/5

2:15 p.m.-12:45 a.m.

1 stop9h 30m

Philadelphia

Tue 5/5

6:17 a.m.-11:39 a.m.

1 stop6h 22m

C$ 444

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Fri 9/1

5:21 p.m.-11:56 p.m.

1 stop5h 35m

Philadelphia

Sun 18/1

6:15 a.m.-11:03 a.m.

1 stop5h 48m

C$ 448

WinnipegWashington, D.C.

YWG - IAD

YWGIAD

Winnipeg

Thu 22/1

9:00 p.m.-4:33 p.m.

2 stops18h 33m

Washington, D.C. Dulles Intl

Thu 29/1

5:37 p.m.-3:07 p.m.

1 stop22h 30m

C$ 462

WinnipegPhiladelphia

YWG - PHL

YWGPHL

Winnipeg

Wed 25/3

5:30 a.m.-3:49 p.m.

1 stop9h 19m

Philadelphia

Sat 28/3

7:50 a.m.-12:39 p.m.

1 stop5h 49m

C$ 477

WinnipegBaltimore

YWG - BWI

YWGBWI

Winnipeg

Mon 9/2

9:00 p.m.-5:13 p.m.

2 stops19h 13m

Baltimore/Washington

Mon 16/2

4:45 p.m.-5:26 p.m.

1 stop25h 41m

C$ 544

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/12

Showing 1-10 of 45 results
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Best time to book a flight from Winnipeg to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland 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 Maryland

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

Currently, October is the cheapest month in which you can book a flight from Winnipeg to Maryland (average of C$ 81). Flying from Winnipeg to Maryland in January is currently the most expensive (average of C$ 846). 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.

Reviews of airlines servicing Maryland

Get insights into the airlines that provide service to Maryland. 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 Maryland. Reviews last updated 28 December 2025.
Get a feel of what it's like to fly with United Airlines,WestJet, andAir Canada from Winnipeg to Maryland by reading reviews from past customers. 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
9,113 reviews
Check prices

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
United Airlines
7.4
Good
9,113 reviews
United Airlines
7.4
Good
9,113 reviews
Check prices

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
WestJet
7.2
Good
3,222 reviews
United Airlines
7.4
Good
9,113 reviews
Check prices

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.
Air Canada
7.1
Good
10,562 reviews
United Airlines
7.4
Good
9,113 reviews
Check prices

Crew

8.1

Food

6.6

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Michelle,Dec 2025

DEN - MKE

I liked that the plane waited 5 minutes for a family whose incoming plane was late. This was the last flight of the day to MKE. Flight attendants actually checked in throughout the flight. Although, not really friendly. Happy to see screens on seat backs again. This is my first time not flying first class in over 10 years. It was economy plus.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Maryland. 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 Maryland?

    Most people fly from Winnipeg (YWG) if they book a flight from Winnipeg to Maryland. Winnipeg is conveniently located just 7.3 km from Winnipeg’s city centre.

  • How long is the flight from Winnipeg to Maryland?

    There are many flights that can get you from Winnipeg to Maryland in 5h 36m. Fly via WestJet to get the fastest option. Airlines will cover a distance of 1976 km.

  • What are the most popular routes from Winnipeg to Maryland?

    The most popular route from Winnipeg to Maryland is Winnipeg - Washington, D.C. Reagan-National. You may also consider Winnipeg - Washington, D.C. Dulles Intl or Winnipeg - Philadelphia.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Maryland 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 Maryland?

    Currently, October is the cheapest month in which you can book a flight from Winnipeg to Maryland (average of C$ 81). Flying from Winnipeg to Maryland in January is currently the most expensive (average of C$ 846). 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 Maryland

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Top 3 airlines flying from Winnipeg to Maryland

Discover the top 3 airlines that operate flights from Winnipeg to Maryland. 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 28 December 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 187AverageC$ 196FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 330AverageC$ 439FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 363AverageC$ 801FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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

Deals for Winnipeg to Maryland flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

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

Millions of users choose and trust Cheapflights to book the best flight deals from Winnipeg to Maryland for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Yes, we can. To see specific flights from Winnipeg to Maryland with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Of course! You can now track prices for flights from Winnipeg to Maryland and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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