Find cheap flights from Wisconsin to Winnipeg

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Find cheap flights from Wisconsin to Winnipeg

Round-trip
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Washington (WAS)
Winnipeg
Fri 11/27
Fri 12/4
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Good to know

Low season

November Best time to beat the crowds with an average 5% drop in price.

High season

December Most popular time to fly with an average 20% increase in price.

Average price round-trip

$338 (avg. price over the last 2 weeks)

Good deal round-trip

$149 or less

Good deal one-way

$129 or less

FAQs for booking flights from Wisconsin to Winnipeg

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Top airlines flying Wisconsin to Winnipeg

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,795 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Boarding was a fast and smooth process. Flight attendants were there to help with carry on luggage if needed. Always nice and do their best."

Cons: "The flight was delayed because one or more of the crew were late. I would suggest that when you board a large flight, start from the rear of the plane, not the front. Having to go past everyone to get to your seat is time consuming and somewhat stressful. The food was super gross. The so called beef bulgogi was not appetizing at all. For breakfast, the food was disgusting."

Pros: "Assertive"
Cons: "Hand out headphones, my phone doesn’t have compatibility."

Cons: "Flight delay"

Cons: "A/C was not working well, cabin was too warm and stuffy. Long delay on take off. Can not hear and understand pilot through PA system."

Cons: "Seem that they turned off the air conditioning once we landed in the cabin got on the warm side."

Pros: "Seats are fine. Ordering system is up to date."
Cons: "After the first two hours of my flight (which I sleep through) I couldn’t buy a drink a soda or anything."

Cons: "Worst first class service. Only came by twice in two hour flight"

Pros: "Crew was awesome. Movie was awesome. Delta always comes through."

Pros: "Crew was nice and welcoming"
Cons: "Well, if our plane had been leaving on time it would've been superb."

Pros: "yes"

Pros: "The service on plane was great and so was the opportunity to check luggage, although I was happy I didn't have to."
Cons: "Boarding from DTW to LAX, we had to stand for a long time on the jetway and it was really cold. It was the holding place after they checked my ticket. Otherwise, it was a great experience flying Delta."

Pros: "Flight was very late- about 45 minutes because of some problem with the "paperwork" they said. It was a beautiful day and the crew was ready to go, but we all sat for a long time before being allowed to leave Madison. It's especially bad when we've all made ourselves arrive at 5am for a 6am flight"
Cons: "on time departure"

Cons: "Basic economy is just another way for the airlines to provide low service and nickel and dime everyone while charging the same prices."

Pros: "súper comfy and got a seat upgrade due to my status so i looove delta. always on time and super friendly staff awesome.!!!"
Cons: "snacks"

Pros: "That I arrived safe."
Cons: "My seat didnt recline my back was in a lot of pain so was my neck. After getting to L.A at 9:52 a.m didn’t get out of the plane till 11:05 then the baggage claim was noted on carousel 2 when in fact it was carousel 3 when I asked a worker she said “I dont know ma’am” waved me off and kept walking. Terrible."

Pros: "The comfort the professionalism of the staff everywhere I went"
Cons: "Little pricey on rental and hotel."

Pros: "Free drink"
Cons: "Flight was over 30 min late to depart, which caused me to miss my connection flight. I haven’t been offered any sort of compensation for the inconvenience"

Cons: "Ran out of snacks by the time they got to my row"

Pros: "The flight itself was fine, boarded on time and arrived on time."
Cons: "A pet peeve of mine is having to check my carry on. They said the overhead bins were all completely full, so I checked my bag at the gate. Come to find out, there were a few spaces left and it wasn't necessary. Really annoying."

Pros: "The crew was fantastic and very carrying when I wasn’t feeling well. They checked on me multiple times! The food was also really good for airline food!"
Cons: "The security process in the Prague airport is so ridiculous. There are security agents who screen you in the baggage drop off line that makes the line take a very long time. Once you finally get your sticker from them it’s a quick trip through customs. Then the pain really begins with a security scan st each individual gate to enter a boarding area for the plane. Then I was pulled for extra security where a male agent touched my but with some sort of swab with no warning. He then claimed to not speak English (with zero accent when I asked him a question). It was a humiliating and very long process all run by delta!"

Pros: "Flight Attendant Precious was just as her name precious and was very impactful in my amazing journey experience."

Pros: "Flying and going fast, plus the people are kool too."
Cons: "That it was a short trip."

Pros: "Everything went as planned!"

Pros: "The flight crew made me feel like my daughter and I were part of the crew. They were so accommodating, professional and funny."
Cons: "I LOVED EVERYTHING ABOUT MY FLIGHT."

Cons: "Was late almost for an hoir."

Cons: "Late"

Cons: "The seat I was assigned did NOT recline !!! I have neck and back problems and I was in so much pain. You need to clearly indicate when a seat does not recline ( as in exit row seats, which are clearly indicated)."

Pros: "The plane, the seating, and the service was outstanding, great entertainment setup with the movies."

Pros: "Good customer service"

Pros: "The flight was on time and not over booked."
Cons: "The seating was cramped. There were mediocre snacks, but no food or entertainment."

Pros: "The crew went out of their way to make sure they got the plane ready as quickly as possible and get us to Jacksonville as quickly as possible."
Cons: "Delta lost the plane for over an hour. After already spending 10 hours in ATL because of an earlier delay due to human error I was extremely disappointed in Delta that my flight out of Atlanta was delayed by an hour because they LOST the plane and couldn’t find it or the truck to bring it to the gate. This kind of error on Xmas eve is embarrassing. Delta didn’t do anything for the passengers affected by this. I was dumbstruck by the apathy of the Delta employees at the gate (the exception was the flight crew, who tried to get the aircraft there earlier). Because Delta did nothing but make error after error I arrived at home 11 hours later than my original flight was booked for on Christmas Eve, missing Christmas Eve Services and family traditions. When I need to get somewhere on time I’ll never rely on Delta after this experience."

Cons: "Seats are so tight so uncomfortable"

Cons: "3.5 hours late."

Pros: "Got me where I needed to go at the price I wanted to pay. - The gals at the ticketing desk were extremely helpful and cheerful."
Cons: "Not my typical Delta experience: -Boarding for special needs was a joke. A literal ‘run-on-sentence’. No more did I get up and they went to the next group. I was almost knocked over in the rush. -The onboard staff was nice enough. However, between the two of them, one of them had a thick accent. Maybe that one shouldn’t be the one making all on board announcements… and please fix the horrendous crackles too!!! -It seemed our pilot was in training… during our short flight a series of right and left turns were made, no effort to avoid turbulence, and the landing was surprisingly hard. It felt as if my spine took a quick jab to my brain as a result! What’s up?"

Pros: "Got me where I needed to go at the price I wanted to pay. - The gals at the ticketing desk were extremely helpful and cheerful."
Cons: "Not my typical Delta experience: -Boarding for special needs was a joke. A literal ‘run-on-sentence’. No more did I get up and they went to the next group. I was almost knocked over in the rush. -The onboard staff was nice enough. However, between the two of them, one of them had a thick accent. Maybe that one shouldn’t be the one making all on board announcements… and please fix the horrendous crackles too!!! -It seemed our pilot was in training… during our short flight a series of right and left turns were made, no effort to avoid turbulence, and the landing was surprisingly hard. It felt as if my spine took a quick jab to my brain as a result! What’s up?"

Pros: "Most comfortable flight I have taken in some time. Spacious seat, power, good entertaiment, attentive flight crew. On time. Not usually a Delta flier, but times and destination made Delta the choice. Turns out a great choice."

Cons: "Too crowded."

Pros: "On time"
Cons: "With a short layiver, it would be nice to have the option to pirchas a sandwich on board"

Pros: "Media access was great, flight was on time and flight crew was pleasant and helpful!"
Cons: "Space between seats/rows was really tight and I'm short. Would imagine for someone taller it would be really uncomfortable."

Cons: "All was well"

Cons: "Wifi didn't work (network wouldn't show up)."

Pros: "I always feel that the flight attendants on Delta truly care about your flight experience. The smile, the attentiveness, the thoroughness and giving you the attention you desire."
Cons: "Ran out of bananas before they got to me, no big deal and it looks like Delta is getting healthier options every year."

Pros: "Our plane had mechanical issue with a parking brake which they left us know about once we loaded the plane. Unfortunately it was going to take to long so they switched us to another plane."
Cons: "Airlines in general need to enforce the carry on luggage rules. If it doesn't match the dimensions for the carry on specks then make the people Check it. Don't let it go. If I paid for a seat and I'm allowed two carry ons then there should be room for them. Don't ask people to check bags because of a full plane. The crew should have there own place to store their belongings, not where the passengers do and take their space. The life rafts need to be easy to get to but again should take up a spot a passenger has paid for their luggage to go. If that is the only space for these items then don't allow passengers to bring two items if in those seats or on the whole plane. It's really disappointing when your told you may have to check your bag because there's not enough room."

Pros: "Got lucky, and got an upgrade!"
Cons: "Good staff on the plane very sweet like. Actually arrived early. Thought we would get breakfast on the flight from Madison Wisconsin to New York City."

Pros: "Cramped hot plane sitting in sun for half hour with no announcements"

Cons: "See above."

Pros: "The boarding process was very well done. Gate agent and flight attendants on top of their game. This is how it is supposed to be done. Thank you."

Cons: "Not a fan of having "final boarding call" announced to run to the gate, only to sit on the plane at the gate for 30 min because of a scheduled delay at my destination. I know the flight wasn't very full, but that cost me an opportunity to eat dinner. I had to cancel a fast food order because I thought I'd miss my flight!"

Pros: "The pilot tried to make up lost time in the air."
Cons: "Due to regulations, our crew had to delay our flight 39 min. This was done the night before. There was no way we were going to make our connecting flight, but no one from United seemed to care. The crew from milwaukee to Houston was rude and unhelpful."

Pros: "The crew was very good."
Cons: "We had a two hour weather delay and 4 gate changes. Had to unnecessarily walk from one gate to the next. Every time we got a. Texted updated we had a new gate number. Frustrating. Then the plane arrived from LaGuardia but there were no flight attendants so we had another 15 minute delay and nowhere to sit. Not happy"

Pros: "Departed / arrived on time, clean, good snack options."

Pros: "Everything was fantastic except I was a little squished; but I suppose that is to be expected on the economy flight. We did land later than expected but it ended up being just fine and I was able to connect to my next flight."

Pros: "the crew was great."
Cons: "quick flight. comfortable seats. lots of leg room"

Pros: "Nothing - missed flight because of bad info from Kayal"
Cons: "Loss of day's vacation - hotel bill, rental car cost and missed concert - all in about $400 lost."

Cons: "La persona que me atendió para abordar y segundo avión con destino a Puerto Rico era una mujer desagradable mal educada trataba mal a toda persona que le estába. Verificando el boarding pass Verguenza me dio que fuera boricua"

Pros: "The crew went above and beyond on this flight. They were continously carrying around juice for us and constantly making sure we were all comfortable. The movies and TV shows were free if you had the united app.overall it was a amazing flight!"

Cons: "Couldn't get direct tv yo work"

Pros: "It was a pleasant flight - nothing too exciting. The staff was lovely."

Pros: "Everyone was so very helpful."

Pros: "Nothing stood out."
Cons: "having to wait for the flight crew"

Pros: "Nothing. Horrible experience all around. Didn't get home till midnight"
Cons: "Kayak sent me a push notification saying flight was delayed. Arrived at airport, it was scheduled for on time. Airline wouldn't let me or my bag on the flight meaning I had to wait in the airport for 4 hours until the next flight out."

Pros: "The planes appeared to be newer."
Cons: "We had very little leg room and my husband had a sore back after the flights."

Pros: "I really liked the price for the exact time I wanted to travel!"
Cons: "A bit cramped."

Cons: "Bumpy plane"

Pros: "Our Stewart on way was nice. Pilet was informative. Let us know what the weather was like and when to expect turbulence. Pointed out land marks as we flew over them."
Cons: "Seating was uncomfortable. Very little leg room and I am short. Can't imagine what it would b like if I were 6 foot instead of 5 foot"

Pros: "Service and comfortable seat"
Cons: "100 dollar baggage fee"

Pros: "Nothing"
Cons: "Flight from mke to Chicago was delayed so long I missed my connecting flight to charlotte. U had to spend the night in ohare airport. Very unhappy with United airlines."

Pros: "I got a window seat"
Cons: "Chair didnt recline"

Cons: "It was cancelled no email no text no call thanks"

Pros: "I got a fair price ticket and plane wasn't dirty ."

Cons: "I was delayed for 6 hrs"

Pros: "Very friendly and kept us up to date with the issues we had with off-loading about ever 15 minutes."
Cons: "It took 50 minutes after we landed to park and get off the plane."

Pros: "Although it was s bit bumpy bcs of the weather, we had the wind with us and we arrived about 30 minutes early."

Pros: "Fast boarding. Flights were on time."
Cons: "Very cramped seating in the back of the plane."

Pros: "I like the United check in person in Milwaukee / kind- helpful- informed. All United personal were polite and professional in spite of many delays , cancellations and upsets."
Cons: "Out going flight to Denver never made it to salt lake . Rebooking barely got us to connecting flights.... but made it we ran to connecting flight and did make connection. Returning, our first flight also never appeared ... two hours and 15 mins of standing in line to rebook We boarded another flight. In Chicago we stood in another line to rebook . Eventua"

Pros: "The staff was efficient, funny, friendly and honest. Smooth landing and good service. Thank you!"

Cons: "Less than friendly staff at the desk. The gate was changed on us and again no United app updates or texts until much later."

Pros: "Smooth ride, professional and friendly crew"
Cons: "Wish the cup "holders" in the tray were deeper"

Pros: "Nothing"
Cons: "United would not put my bags on despite being at the counter 40 minutes before the flight. Then they put me on stand by for 6 hours during which time they lost my bags and ultimately not having a seat for me."

Cons: "Need water offered free"

Cons: "Plane 2.5 hours late"

Pros: "Flight itself was fine"
Cons: "3 hour delay taking off"

Pros: "It was a wonderful flight. For such a small plane, it was asmooth takeoff and landing. The flight attendant was very friendly too."
Cons: "No snack provided."

Pros: "On time. Early."

Cons: "Nothing was fine"

Cons: "Emergency landing with no power in flightn"

Pros: "This plane was pretty small (70 people) and not full, so boarding was fast. The crew was good, friendly and helpful. The pretzel snack things were good and unexpected for such a short flight."
Cons: "The plane was very loud and it was impossible to hear the crew and my partner. There was no entertainment which was fine because I brought my own."

Pros: "Agents checking baggage were unbelievably slow. Good thing there wasn't a long line."

Pros: "Every thing was ok"

Pros: "The crew was great. I don't know how to make the stars increase."
Cons: "Arrival times were accurate. Crew friendly and helpful. Freight was good."

Pros: "The Flight attendant and pilot were beyond helpful and apologetic about the delay, The customer service rep in Denver was great."
Cons: "Because of a 2+ hour delay in Milwaukee we missed our connecting flight in Denver to Medford and had to stay overnight. Sitting in isle 1 was uncomfortable and it was a pain not having immediate access to my purse because I had to stow it for take off and landing."

Pros: "Awesome flight , great crew, couldn't ask for better"

Pros: "Very smooth and speedy flight, arrived early!"

Pros: "The timing of the flight for Tuesday night was right I don't have that much delays !!!"

Pros: "Quick"
Cons: "Flight attendant was over worked. Flight was delayed. Small carry-on compartments"

Pros: "Flight was smooth and in time."
Cons: "Staff at General Mitchell airport (MKE) United counter were not knowledgeable and the check in process was very frustrating. There were not many people at the check in counter, but it took us 30 minutes to check in once we were at the counter working with the check in clerk."

Pros: "The trying to accommodate crew"
Cons: "Sitting on the plane in the gate for 1 1/2 hours, then asked to leave the plane. Flight arrival time was to be 10:00 pm, instead arrived in Winnipeg at 12:35am."

Cons: "The delays and poor customer service."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Wisconsin to Winnipeg

Airlines flying from Wisconsin to Winnipeg have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Wisconsin to Winnipeg

Recent round-trip flight deals

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