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Find cheap flights from Chicago O'Hare Airport to Winnipeg

ORD - YWG

Find cheap flights from Chicago O'Hare Airport to Winnipeg

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Chicago (ORD)
Winnipeg
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Good to know

Low season

October Best time to beat the crowds (36% less expensive on average)

High season

April Most popular time to fly (29% more expensive on average)

Average price round-trip

C$ 563 (avg. price over the last 2 weeks)

Good deal one-way

C$ 213 or less

When to book flights from Chicago O'Hare Intl to Winnipeg

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 271 or less one-way.
  • High season is considered to be March, April and May. The cheapest month to fly is October.

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Top airlines flying Chicago O'Hare Intl to Winnipeg

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,916 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "The carrots were hard and the bread was cold."

Pros: "Comfortable plane due to few passengers"
Cons: "7 hour delay after flight postponed."

Cons: "I would ask that the gate does not share in detail reason for delay in seat assignment is related to getting a family sitting together when the basic rules should apply unilaterally."

Pros: "Got to my destination without any issues"
Cons: "Seats/seating area are too small, and I'm not a big person."

Pros: "No"
Cons: "The flight was delayed almost 6 hours, the crew was rude and the “comfort +” seats had very little leg room ."

Pros: "The flight was on time, the crew was pleasant and looked like they enjoyed working in the air."
Cons: "Our second time on a 787 Dreamliner across the Atlantic as about the same as the the first. The seat pitch is very tight so when a passenger reclines into the next row the seatback nearly touches your face. The Dreamliner seats seem to be very hard and it's difficult to get comfortable."

Cons: "No AC for an hour before takeoff - very uncomfortable. Audio for tv did not work."

Cons: "Flight was delayed a bit due to a couple passenger booking/misc issues. 1st class didn’t get gate bevfood service. Oven was busted so my meal wasn’t available. Entertainment console had all channels functional except — not really an issue I just really wanted to have ESPN playing in the background"

Pros: "Son got wings, so was happy."
Cons: "No entertainment."

Cons: "It was late"

Pros: "Good snack selection. Crew was personable."

Cons: "Seat assignment for me and my traveling companion was done at gate. We had to sit in 2 different rows."

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

Pros: "The boarding was fast and very well handled."

Cons: "My flight from Chicago was two hours late and that's why I missed the flight from Atlanta to Buenos Aires. No one helped and did not know that the flight was delayed and I had to find a place to sleep. I'm not satisfied with the experience and I have not yet arrived in Argentina because of the whole"

Pros: "N/A"
Cons: "Chinese Eastern did not try to help and solve my problem."

Pros: "There was a bit of a mixup in boarding the plane but otherwise the flight was good. There was no entertainment system on this short flight. The flight attendants were very pleasant & efficient. They only served snacks on this short flight but were very good at ensuring everyone had at least one or more beverages. The premium seats were very comfortable ."

Pros: "Short flight"
Cons: "Flight attendant was not willing to go above and beyond as he stated he would. My husband asked for a coke and the flight attendant told him he could only get water."

Pros: "On time departure/arrival despite weather in Atlanta. Always a fan of free messaging and choice of snacks."
Cons: "Delta needs to invest in their gate area at ORD. Understand it’s not a hub but it’s a key business/leisure destination. The MD-80s are ok for a short hop but over 1 hour unless you’re in Comfort+, it’s tight."

Pros: "Snacks, cleanliness and crew"
Cons: "N/A"

Cons: "From the begging they changed the flights for something totally different. It was a 14 hour trip. Awful"

Pros: "Nothing"
Cons: "They take them forever to find me another fly ,make miss my other fly, my work my time and my sleep"

Cons: "Entertainment app from Go Go didn’t Work."

Pros: "It was a normal flight as well expected."

Pros: "I was with my friend"
Cons: "Delayed 12+ hours"

Pros: "We had a 2 1/2 delay due to mechanical issues but the crews, flight and ground, did a great job. Thanks."

Pros: "I was given a complimentary upgrade."

Pros: "The crew and pilot were absolutely amazing."
Cons: "This is my 3rd delta flight in a row that has been delayed. I understand these things happen, just extremely frustrating."

Cons: "It takes time and worries to find the air train and Aeroflot registration."

Pros: "My flight was great. Boarding was easy and the seats were comfortable."

Pros: "I needed to run real fast to the connection flight and gladly got there on time."

Pros: "The service was amazing , the staff was honestly friendly and nice"

Pros: "Great service, nice agent friendly"

Pros: "Very friendly and professional gate agent and flight attendant"

Cons: "I was unable to fly at all due to a spelling error on my ticket. The airline refused to alter the ticket. Worst experience of my life, ruined my Christmas"

Pros: "Very nice flight and attentive staff. Enjoyed the view of NYC as we flew up the East River, then looped over Nassau County to approach LGA."
Cons: "The male flight attendant who handed out the complimentary drinks and snacks acted a bit strangely. I was very thirsty, and I asked him if I could keep the rest of the can of soda. He neither said yes nor no, but rather completely ignored what I said and just poured my drink and moved on. I was a mildly annoyed, but figured maybe it was policy and he was shy and didn't want to debate the matter. When he took care of the older couple behind us, however, things got really strange. He asked them whether they wanted pretzels or peanuts, but they misheard him and asked for a ginger ale. I happened to know that he did have ginger ale, since my wife had just gotten one, but rather than just pouring the old folks a drink, he repeated himself. "Peanuts or pretzels?" They misheard again and asked him whether he had a diet ginger ale. Again, rather than just pour them the drink, he repeated himself. "Peanuts or pretzels?" This went round and round a few more times -- like a poorly designed computer UI that refuses to accept anything except the correct input -- before the old couple finally figured out the disconnect and picked their snacks before their drinks. Very weird."

Cons: "Layover"

Pros: "Short flight"
Cons: "Too cold Not friendly boarding agent"

Pros: "N/A"
Cons: "2.5 hour delay for no apparent reason at first (supposed mechanical issues with plane) and then waited on plane at gate for a missing pilot who never got picked up from his airport and got stuck in Chicago traffic trying to get to O'Hare. Eventually had to take pilot from another flight before leaving at 8:45 when flight was scheduled for 6:00am."

Cons: "Had a death in the family and no one would help me get back home"

Pros: "Seats were comfortable. Snacks!!! Nice flight crew."
Cons: "I liked everything."

Pros: "The Gogo Inflight wifi and entertainment did not work for even a minute. I choose flights based on their amenities and this one had offered full WIFI service which swayed me to choose to fly with Delta. I'm not sure who is to blame about this issue but I'm pretty frustrated that it was completely dysfunctional."

Cons: "Plane was sat broken at gate and needed part to be flown in. 150 minutes delayed. Not acceptable."

Pros: "I missed my flight for the first time and I was having a complete meltdown at the check in desk until the sweetest agent said "oh no worries sweetheart, let's find you another flight back home"... It seems so simple but with the morning I had, this simple act had me in tears! The kindness and patience she showed me was amazing and definitely the reason I will always fly Delta to any and every destination they are able to take me! <3"

Pros: "No fee to get on an earlier flught"
Cons: "When I tried to rebook online this flight was not an option"

Cons: "I am a 5'3" 125# woman who, unfortunately, had a middle seat assignment. The passenger to my right, on the aisle, weighed approximately 375# and took up 1/3 of my seat. The arm was not able to go down comfortably, and when it did it was not usable . The passenger on my left, window seat, was probably 6'7" and had to sit with a man spread in order to fit. I could not move and was extremely uncomfortable. The plane was overbooked so I was unable to move. Therefore, worst flight ever. Plus, I paid for a full seat and was only able to occupy half of it."

Pros: "The in-flight service was good."

Pros: "Nothing"
Cons: "Poor hospitality by alaska airline staff, especially by MrPavel at gate H4, 01nov2016, prior boarding around 0730am"

Cons: "No entertainment."

Cons: "Good flight"

Cons: "They loose my luggage!!!!!!"

Pros: "Nothing"
Cons: "Flight delay led us to miss our connecting flight. Air Canada then lost our luggage for 6 days on our honeymoon!"

Cons: "Delayed without notice and broken sound system for tv screen."

Pros: "Extremely helpful and accommodating! Thanks to all!"

Cons: "I could not get a seat assignment or a boarding pass for my connecting flight"

Pros: "Not much."
Cons: "I thought Comcast service was bad. This was the worst. They cancelled my flight at the last minute, then escorted all passengers out of the gate, told us to go through customs then pick up our luggage. And said we had to call to arrange another flight, but the phones just left a message saying to call back in a few days. I was stranded with no phone, no hotel, and no flight home. Three days later, I still cannot get in touch with them."

Pros: "The pilot seemed good and the staff on the plane were nice overall"
Cons: "Customer service from the group staff that checked us in was horrendous... (Lisa from Chicago ). We were not aware one of us needed eTA to fly through Canada and the agent was so belittling, rude and plane wrong with her information, that if it had not for our smarts, we might have not made it to our destination. I do not spend so much money to fly with an airline, whose agents treat it me like this! She really should be fired for her terrible manners and for giving customers wrong information..the second supervisor we talked to helped us, but the impression we got from the agent was so terrible, that it was hard to feel any good...no food on a flight during lunch hour, seems unfitting."

Cons: "My original flight was delayed by 3 hours, causing me to miss my connecting flight. Instead of arriving at 9:30 at my final destination I arrived at 1:30 am. Exhausted."

Pros: "I am sad to say I have little positive things to say about this experience."
Cons: "To begin, our flight was delayed an hour into Toronto. We asked the flight attendant about our connecting flight and they said they would find an answer. It ended up that we landed just as the flight was scheduled to leave. Why they could delay pur flight but would not hold another flight by 20 minutes is very questionable. Then we got to customer service, the rep told us that we could only get on the next flight going out tomorrow at the same time which meant 24 hours lost. Of our vacation- which hotels already booked and tours already booked. When I asked if there was anyway we could get in earlier the service person told me "I should be grateful because some people have had to wait multiple days to get to their destinations." When we finally did board the flight the next day we were not served any food, no snacks, and no drink for the entire overnight flight."

Cons: "There was a 90min delay on all flights going to toronto due to construction in toronto yet air canada (knowing this) boarded everyone on time anyway and made us sit on the runway for over an hour. They could have left us in the lounge until they were ready. Parents with babies do not appreciate such thoughtlessness. But hey, as far as air canada was concerned, they left the gate on time."

Pros: "The crew members were also friendly"
Cons: "The boardung gate was changed but no announcement was made"

Pros: "The staff was helpful and courteous. I liked the tv selection especially the Canadian content."
Cons: "The flight was delayed because of electric problems. The complimentary snacks aren't as good as other airlines."

Pros: "It was such a nice normal flight compared to the other flights on this trip."
Cons: "Still too much carry on to deal with before take off."

Pros: "Paid for the "upgraded" seat only to be told we had to be in the back of the plane. Moving back all rows had one person and one chair open, so we had to sit apart. Useless crew as an elder couple asked to sit together and were told to check with passengers. Oh and the flight was delayed 3 times."

Pros: "In the airport Chicago to Montreal I met a nice person he made my boarding pass to me. I love the service !!!!!! Said Thank you so much for your time to getting. Dory Clothilde"

Pros: "The landing..."
Cons: "Left late and overall once again did not find the staff to be exceptionally helpful."

Pros: "Food and staff."
Cons: "Rushed to get connection flight at Vancouver. The official One hour 10 minutes connection time shrunk down to about 45 minutes, which is too short considering that most flights leave late from Chicago with an overly busy airport take-off schedule."

Pros: "The ever wonderful Air Canada cancelled a bunch of the flights that I had originally booked 2 months before I left and marooned me in the Toronto airport for an 8 hour layover on my way home. Unacceptable. No reason given, no apology made, nothing."

Cons: "They lost our luggage and we didn't get it all back until about 7 days after we arrived! 7 Days!!!! Customer service was horrible and we were traveling with a small child."

Pros: "Flight was smooth; love being able to track route. Got in early."

Cons: "Flight was delayed but overall trip was good"

Pros: "Quick easy, I hate that I have to go through sercurity again... but oh well."
Cons: "Refer to last one."

Cons: "My flight was changed and I wasn't informed - I cleerly checked my information beforehand but it would be nice if flights were to change by two hours, to know in advance so arrangements could be made"

Cons: "It was so great we didn't go. Got a refund you retards"

Cons: "Flight was 45 min late leaving & I only had 1 hr between the next flights. Because Winnipeg is a small airport, I just made the next connection but no time to go to the restroom."

Pros: "We checked in online and were able to very quickly and efficiently check our bags and board."
Cons: "We did not have in flight entertainment. We had to pay $10 to rent an iPad."

Cons: "Taxied to runway, but had to go back to terminal due to one seat not staying in upright position. Flight was about an hour late then."

Pros: "Price good; seat comfort OK."
Cons: "Late to board, late to take off, late to land: no explanations other than "We're third in line.""

Cons: "The engine was making an unusually loud whirring sound. Felt concerned that the plane was not fit to fly."

Cons: "Did not appreciate not having a movie screen. Renting an iPad for such an expensive flight is not good business."

Pros: "Provided a blanket and pillow, breakfast and dinner, had 3 bathrooms which was excellent for how many people on the plane. The flight attendants were excellent and very nice as well. I do love air canada for long flights."
Cons: "When i checked out the cabin after i bought the tickets i was under the impression that there would be screens on the plane to view movies for free. Instead they were offering for $10 to buy a ipad and more money for headphones to rent for the flight to watch movies. Kind of was a disappointment but i read a book which is always better to do anyway."

Pros: "The crew was very nice."
Cons: "It was like flying in 1995. They may want to consider buying more modern planes."

Pros: "This is awful flight coz I brought it from kayak"
Cons: "Flight delayed due to plane defect. Stayed in plane for more than 5 hours. Baggage lost. Never made it on time"

Pros: "the crew was great, food was alright, and overall I enjoyed my flight"
Cons: "the only entertainment was able to connect to apple products or a renatble iPad. I don't have an apple product so that was a bit annoying"

Pros: "The crew on the flight was nice, and the entertainment was good."
Cons: "Our first Air Canada flight was 2hr delayed due to mechanical error. After a 2hr delay, we finally flew for 1hr, had awful turbulence on the way down, and got to Toronto only to find out there was no customer service desk. We missed our connection with Luftanza and had to fly Air Canada again. First off, we couldn't get on another flight until the next morning. Then the desk never called the hotel they gave us the voucher for, so when we showed up at midnight the hotel was fully booked and had no room for us. We had to fly into Heathrow instead of Gatwick (final destination was Brighton for an international conference). We missed the entire first day of the meeting and had to rent a car for 65 pounds each to take us to Brighton from Heathrow, finally arriving at our hotel by midnight. The customer service was non-existent for Air Canada. We literally are going to have to email them."

Pros: "The flight was comfortable. Entertainment choices were varied and generous."
Cons: "o'Hare needs an upgrade."

Pros: "How quick it waz"
Cons: "How close the seats were"

Pros: "Friendly crew. Very smooth flight. Easy to navigate terminal."
Cons: "Nothing!"

Pros: "I liked the way they handled the rain delay. Although inconvenient, they were transparent with the process"
Cons: "The lack of certainty whether we were removed or stilling our connecting flight to delay."

Pros: "On board service Comfortable seating and space On time dep. & arrival"
Cons: "None"

Pros: "The crew was good!"
Cons: "I wished that there were opportunities given for beverages. I also would have liked more explanations on how to connect to the entertainment."

Cons: "gate was changed without an announcement flight was twice delayed"

Pros: "The crew was friendly, there was entertainment available via the display on the back of the seat."
Cons: "The touchscreen display wasn't working properly, making it difficult to control things like volume. I would have preferred a display with physical buttons that took a bit more time than the weirdly synced touch screen"

Pros: "I am happy that Air Canada is unionized; the personnel are fine. I also like the tvs on the backs of the seats, with their wide range of shows. Particularly, I like Portlandia, though there was only one episode of that."
Cons: "I disliked that the airline forced me to miss my connection (inevitable, I suppose, given the excessive security and the lack of direct, affordable connections between Manitoba and the US) and I had to take a later flight to Toronto and didn't get home until 2 am."

Pros: "Good"
Cons: "Ok"

Pros: "Services"
Cons: "N/A"

Pros: "Nothing."
Cons: "Everything, but specially the boarding crew was unprofessional and very rude."

Pros: "Nothing,Bad customer service and terrible accomodation. Will never use it again."
Cons: "Where do I even start. I was issued a ticked with which I required a canadian transit visa which was never mentioned anywhere. Now I had to get a whole new ticket because you didn't refund me anything. Thanks for that. Never using you guys again."

Cons: "paid for a exit row window and after a two hour delayed flight I was seated in a aisle seat not on the exit row like I paid for."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago O'Hare Intl to Winnipeg

Airlines flying from Chicago O'Hare Intl to Winnipeg have enacted additional safety measures and adjusted policies to better accommodate travellers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Chicago O'Hare Intl to Winnipeg

Mandatory masks

Masks required on board, masks provided on flights from Chicago O'Hare Intl to Winnipeg

Social distancing seating

Middle seats unavailable to book on flights from Chicago O'Hare Intl to Winnipeg

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago O'Hare Intl to Winnipeg

Book cheap flights from Chicago O'Hare Airport to Winnipeg

Recent round-trip flight deals

16/6
Wed.
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Multiple Airlines
4h 04m
ORD - YWG
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7h 16m
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9h 03m
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10h 44m
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