C$ 268 Find Cheap Flights from Winnipeg to Maryland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Maryland departing on 1/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Maryland

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Maryland, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Maryland, as well as popular online travel agencies
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Cheap Flights from Winnipeg to Maryland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Maryland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Maryland

Wed, 8 Jul - Sun, 12 Jul
United Airlines Logo
7:00 a.m. - 2:47 p.m.
YWG
-
PHL
6h 47m
1 stop
United Airlines Logo
6:00 a.m. - 11:52 a.m.
PHL
-
YWG
6h 52m
1 stop
C$ 506United Airlines
Sat, 4 Jul - Tue, 7 Jul
Air Canada Logo
5:00 a.m. - 2:49 p.m.
YWG
-
PHL
8h 49m
2 stops
Air Canada Logo
4:20 p.m. - 11:20 p.m.
PHL
-
YWG
8h 00m
1 stop
C$ 524Air Canada
Wed, 26 Aug - Mon, 31 Aug
Multiple Airlines Logo
7:00 a.m. - 11:17 p.m.
YWG
-
IAD
15h 17m
2 stops
Multiple Airlines Logo
7:00 p.m. - 11:10 a.m.
IAD
-
YWG
17h 10m
1 stop
C$ 527Multiple Airlines
Thu, 18 Jun - Mon, 22 Jun
Multiple Airlines Logo
5:10 a.m. - 9:48 p.m.
YWG
-
DCA
15h 38m
2 stops
Multiple Airlines Logo
8:40 p.m. - 8:40 a.m.
DCA
-
YWG
13h 00m
1 stop
C$ 536Multiple Airlines
Thu, 13 Aug - Sat, 22 Aug
Air Canada Logo
7:10 p.m. - 10:09 a.m.
YWG
-
PHL
13h 59m
1 stop
Air Canada Logo
10:05 a.m. - 3:14 p.m.
PHL
-
YWG
6h 09m
1 stop
C$ 538Air Canada
Tue, 2 Jun - Wed, 3 Jun
United Airlines Logo
12:56 p.m. - 9:19 p.m.
YWG
-
PHL
7h 23m
1 stop
United Airlines Logo
6:00 a.m. - 11:52 a.m.
PHL
-
YWG
6h 52m
1 stop
C$ 565United Airlines
Thu, 25 Jun - Wed, 8 Jul
WestJet Logo
7:00 a.m. - 6:59 p.m.
YWG
-
DCA
10h 59m
2 stops
WestJet Logo
6:00 a.m. - 11:53 a.m.
DCA
-
YWG
6h 53m
1 stop
C$ 726WestJet
Thu, 25 Jun - Wed, 8 Jul
WestJet Logo
7:00 a.m. - 6:59 p.m.
YWG
-
DCA
10h 59m
2 stops
WestJet Logo
6:00 a.m. - 2:25 p.m.
DCA
-
YWG
9h 25m
2 stops
C$ 737WestJet
Tue, 25 Aug - Sun, 30 Aug
Delta Logo
12:46 p.m. - 9:30 p.m.
YWG
-
BWI
7h 44m
1 stop
Delta Logo
6:05 a.m. - 3:08 p.m.
BWI
-
YWG
10h 03m
1 stop
C$ 946Delta
Wed, 17 Jun - Tue, 23 Jun
Delta Logo
6:40 a.m. - 6:33 p.m.
YWG
-
BWI
10h 53m
2 stops
Delta Logo
6:19 a.m. - 11:56 a.m.
BWI
-
YWG
6h 37m
1 stop
C$ 987Delta
Booking Insights

KAYAK's insights & trends for Winnipeg to Maryland flights

Get data-powered insights and trends into flights from Winnipeg to Maryland to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Winnipeg to Maryland?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Maryland departing in July.

What is the cheapest month to fly from Winnipeg to Maryland?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Maryland, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Maryland is February, when tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are January and September, when the average cost of round-trip tickets is C$ 874 and C$ 814 respectively.

Good to know

Low seasonOctober
Cheapest flightC$ 268
Best time to beat the crowds (82% less expensive on average)
Most popular time to fly (5% more expensive on average)
Flight from Winnipeg to Philadelphia

FAQs - booking Maryland flights

  • How does KAYAK find such low prices on flights from Winnipeg to Maryland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Maryland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Maryland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Winnipeg to Maryland is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Maryland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Winnipeg to Maryland with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Maryland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Winnipeg to Maryland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines flying from Winnipeg to Maryland

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Maryland. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Winnipeg to Maryland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9736 reviews
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
8.1Crew
Airline reviews

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

10.0 ExcellentEirene, May 2026
YYZ - EWR
Read more United Airlines reviews

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

They were fast and I like how they used to entertainment system to play video about the safety.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

Flight attendants had a little attitude. Food tastes no good.

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Could not make the flight. No one would help us at all

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Crew at gate and onboard were just very OK, not very friendly and honestly seemed bothered to be there. I will give a shout out to still selling headphones for those who forgot.

Flight Boarded and departed on time. The Flight crew was very friendly and accommodating. The aircraft was clean and free from clutter and debris. I will be happy to recommend Air Canada to my friends and relatives for their flight needs. They were very attentive and responsive to our needs as Senior citizens.

Another good flight experience with Air Canada. The business section did not feature the full length sleeping arrangement, but this was a shorter trip. The food was excellent. But the flight crew was truly top tier: friendly, cheerful, helpful at all the right times. Air Canada truly outshines all U.S. carriers.

Flight operated by PAL. We boarded, and one engine started. The crew found some problem that could not be fixed. The flight was canceled. This run from yhz-bos is very unreliable.

Everything. The crew was so friendly, helpful & smiled. We had an excellent flight getting in earlier.

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Everything you need to know for your flight from Winnipeg to Maryland

Information on your arrival and departure airports