ORD - YWG

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ORD — YWG
20 May — 27 May1
Return
1 adult
Economy
0 bags
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Fri 20/5
Fri 27/5

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Good to know

Low season

October

High season

April

Cheapest flight

C$ 194

Average price round-trip

C$ 566

Good deal one-way

C$ 375
Best time to beat the crowds (36% less expensive on average)
Most popular time to fly (29% more expensive on average)
Flight from Chicago O'Hare Intl to Winnipeg
(avg. price over the last 2 weeks)
or less

When to book flights from Chicago to Winnipeg

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 375 or less one-way.
  • High season is considered to be March, April and May. The cheapest month to fly is October.
  • Morning departure is around 41% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Chicago to Winnipeg flights

Top 3 airlines serving Chicago O'Hare Intl to Winnipeg

Scores according to KAYAK customer reviews
7.7
WestJetOverall score based on 9166 reviews
8.1Boarding
7.7Comfort
8.5Crew
7.0Entertainment
7.1Food
Airline reviews
Cons: "Aka was happy with westjet"
Read more about WestJet
Cons: "Aka was happy with westjet"
Pros: "Crew was good"
Cons: "Montreal airport was awful"
Pros: "yes every thing was good.."
Pros: "No one disturbed me while sleeping and crew was helpful when I woke as bad needed refreshments."
Cons: "More leg room"
Pros: "Crew was great."
Cons: "Communication as to why we were promoted to premier seats and service."
Pros: "Fast efficient process through security. Well labeled and helpful airport staff. Plane wasn’t very full. Had a row to myself which was great. Entertainment available on smartphone, iPad or lap top."
Cons: "Really fast connection. 20 minutes from landing from LAX to clear customs and find connection before boarding call. Not much menu options for purchase and too quick a connection to buy anything. Luckily I travel with snacks."
Pros: "Crew was very helpful"
Cons: "Gluten free snack that is free"
Pros: "Efficient and fast boarding and getting things ready"
Cons: "Seating is horrible. Not just the space but the cushion-or lack of"
Pros: "Good crew!"
Pros: "Crew is always polite and friendly"
Pros: "Loved the trip"
Cons: "My tv was not working, landing was not smooth staff was rude specially Edward"
Pros: "The flight didn’t get cancelled. We didn’t crash."
Cons: "Flight was delayed because it came from Toronto and it needed to be cleaned."
Pros: "On time. Smooth."
Cons: "Cramped seating"
Pros: "Smooth trip."
Cons: "No one would get a wheelchair to get to cart that was on different floor. Driver didn't volunteer to carry bags to cart."
Cons: "Later flight from Toronto delayed multiple times, finally to 2:40 am and then canceled at midnight. Way too late to find an affordable hotel, had to stay at expensive airport hotel instead."
Pros: "I loved how spacious the plane was. The seat was comfortable with lots of legroom."
Pros: "It was smooth and uneventful."
Cons: "It was all fine."
Pros: "I like everything else except no entertainment"
Cons: "I wish there is TV or newspaper, magazine to read or watch that helps."
Cons: "Flight was delayed due to a tire change. That’s no big deal, but the crew did not accurately keep us updated on the actual loading time in order for me to arrange my pickup upon arrival in Winnipeg."
Pros: "great on board crew, very friendly and getting the impression the company execs under value them. PAY YOUR STAFF BETTER WESTJET."
Cons: "older equipment often means what you’re accustomed to is missing. specifically, not being able to plug in and charge proved problematic on this flight. in-flight entertainment was the old back-of-seat and did not work until the final minutes of the flight."
Pros: "The check in staff are very helpful and kind especially Rachel! The service was excellent very happy and helpful staff during our flight. The pilots made such a smooth landing and we are so thankful to be home safely!"
Cons: "Still cramped in the seats!"
Pros: "Westjet crew is fantastic!"
Cons: "Wish it could have been a longer flight to enjoy the WestJet crew’s hospitality longer"
Cons: "Flight delayed 2 hours, missed connectionplus an hour on the tarmac"
Pros: "There is no entertainment so why ask.this question repeatedly and I understand on longer flights that is valid but on these flights it is not applicable"
Pros: "Absolutely nothing about this extremely delayed flight"
Cons: "I was stuck at Pearson International for 5 hours before I was able to get on a different, direct West Jet flight which also ended up being severely delayed."
Cons: "Of the four flights I took with WestJet this holiday, 3 were delayed. The flights were frigid. On this flight the agent at the gate was very rude when I asked about checking my bag, lecturing me about the size of the bag and insisting she would have to charge me if it was a full flight, which she said it wasn’t. It ended up fitting just fine in the overhead. Totally soured my experience. I will not use this airline again."
Pros: "The leg room"
Cons: "They didn’t have wifi so couldn’t watch anything"
Cons: "WestJet needs more checkin machines and shorter security lines. I arrived at the airport with a boarding pass and it took over an hour to get to the gate"
Pros: "Friendly staff 8"
Cons: "Seats were so crammed together. When the person in front mived their headrest back my knees were crushed and I xould not sit comfortably. I am 5'10. Not super tall. Nees more leg room."
Cons: "Cabin was too cold"
Pros: "Crew"
Cons: "Delay"
Pros: "Great service. Friendly. Connections are well timed so you dont have to wait long to transfer."
Cons: "the seats are a bit confining."
Pros: "Pleasant staff and adequate leg room."
Cons: "If it was noted that there would be luggage fees when I was booking I didn't see it."
Pros: "The flight over all was good. Service, and delivery of the expectations were good. Even though the items listed in the dislike are 3 in number, and added to an uncomfortable experience, some of them are identifiable as beyond control, yet others are within the control of system set up or process."
Cons: "small items that I didn't like were : 1) Temperature, and 2) wifi 3) waiting for electrical. 1) Temperature: When boarding the plane the Temperature of the cabin was extremely warm. The pilot advised of the condition, this was not something that could have been fixed and I think they handled it well. I just didn't like the 90+ temperature 2) Wifi: was intermittent, I ensured the Westjet app was the only one running, but the movie I was watching was pausing every 15 minutes to buffer. So it was a constant reminder of dial up.... 3) waiting for electrical: Upon landing and taxi-ing to the ramp, the pilot was advised that there was no electrical to support the plane after he turned off the engines. So good that he waited, thank you pilot, and not so good as it was another unpleasant item on the plane ride."
Pros: "Friendliest crew, good entertainment system. Comfortable seating"
Cons: "Desperately need a lounge facility in terminal 5 Chicago"
Pros: "Crew were all very welcoming and polite"
Cons: "Food and entertainment were pretty pricey."
Pros: "Entertainment"
Cons: "Late leaving, hot in plane, sat on tarmac for 40 mins"
Cons: "Got there 2 minutes after check in closed and wouldn't let us fly"
Cons: "Good airlines"
Pros: "Price, staff"
Cons: "Uncomfortable seats, no padding, very hard. At Pearson you have to walk about half an hour to get to West Jet gate."
Pros: "Friendly, helpful staff"
Cons: "Typical stuff, Cramped space, crappy food"
Pros: "Crews"
Cons: "Should be more hearty food and more entertainment like tv, movies and radio"
Pros: "It was a little bit delayed but after the airplane arrived everything was very fast."
Cons: "I don't have any problem about the west jet, I know that some delays is complete normal because the weather or air traffic."
Pros: "Boarded easily, took off and landed early. What's not to like?"
Cons: "Was offered beverage once, water once. Flight was 4.25 hours long. Would have liked first service to offer snacks besides cookie-- usually ask if you want food for purchase."
Pros: "Friendly staff"
Cons: "Having to pay for luggage and my boarding pass didn't state what zone I was so I had no clue as they didn't mention seat numbers at all."
Pros: "Great service and flights were on time."
Cons: "The lounge should offer more variety of foods ."

Check in and security were a disaster and resulted in a 1 hr delay

Pros: "nothing"
Cons: "smell, old chairs, lights on the entire time"
Pros: "Everything went according to schedule, staff was suoee friendly and helpful."
Cons: "Not enough leg room"
Cons: "Went to check in baggage and had my paid receipt and Aeromexico insisted luggage wasn’t paid for and we had to double pay at the airport so we didn’t miss our flight! RIDICULOUS! Wake up Aeromexico and KIWI booking!!!"
Pros: "The crew"
Cons: "No delays. Had delays on both flights."
Pros: "The services and the comfort"
Cons: "Everything its good"
Cons: "Attendants were rude or looked at me like I was inconviniencing them. Not good service at all."
Pros: "Very friendly crew, plenty of drinks. Easy and organized boarding process"
Cons: "Free WiFi would be nice"
Cons: "I missed my connection because my flight was delayed 3 hrs, no one told me not no pick my suitcase because it was going straight to my final destination, there is not good communication and I had to stayed 9 extra hours in the airport."
Pros: "They provde fod and dinks"
Cons: "Baggage fees"
Pros: "I missed my connection flight. I couldn’t get my situation fixed and got stranded in Mexico City because of the most horrendous service I have experienced in my entire life."
Cons: "The organization for boarding. Communication and costumer service. I am really disappointed on this airline"
Cons: "I am assuming because it was a Delta airplane we didn’t have the option to watch movies. The Aeromexico planes always have monitors to watch them. I missed that on this flight."
Pros: "I liked how staright-forward the whole process was. No different if I was flying anywhere else. I didn't feel like I didn't know what was going on because I didn't speak Spanish."
Cons: "My personal hand bag was taking away from me. I couldn’t carry with me and it was open and stolen my new pair of Jordan shoes Thanks"
Pros: "Evrething"
Cons: "All"
Pros: "The. Flight was on time,I checked in online and that saved me alot of time at the airport."
Pros: "Great prices!"
Pros: "Amazing service, clean plane, complimentary food and drink included is a great perk. Too bad other airlines don't treat you this well! My first choice for all future flights to Mexico. Gracias AeroMexico."
Pros: "service was good"
Cons: "There was no Wi-Fi even though there was signs in the plane of Wi-Fi availability"
Cons: "Ran out of fuel and had to make atop at St. Louis for about 1-1/2 hrs So got delayed needed to get to Chicago at 11 and ended up at 1:30"
Pros: "Friendly flight attendants, good service."
Cons: "Entertainment system didnt work on the way to Mexico."
Pros: "Service"
Cons: "Charge for baggage"
Cons: "Was late 2 hours"
Pros: "That they got us there early. The crew was attentive and well dressed."
Cons: "Toilets were too small. Rows on this flight were to close together. Boarding very slow."
Pros: "Nothing I got charged for canceling my flight!!"
Cons: "I paid 242 dollars for my ticket and they charged my card 150 for canceling it!!! Will definitely not fly this airline ever again!"
Cons: "THE FOOd"
Cons: "thought your carry on luggage rules were more relaxed. however we ended up getting charged an extra $80 for 2 carry on bags that were overweight. never had an overweight restriction on a carry on before."
Pros: "nothing"
Cons: "2 1/2 hour wait in line to check in. then had to rush to gate to make it 10 minutes before take off. Charged us $50 for I am not sure what. Only had 2 carry on bags Had reserved earlier seats but was not honored. Sat in last row on plane next to bathrooms. I will never take this f....n airlines again. Rather pay more or be inconvenienced than deal with this incompetent, greedy so called airlines."
Cons: "1) we lined up to board on time, and then were told one crew member was late- 2 hour delay. 2) because several dozen aeromexica employees were on the flight and boarded first with tons of carry on luggage, all passenger carryons had to be checked, 3) upon arrival at ord at 1am, over 2 hour wait for luggage, with no explanation by staff"
Pros: "Good service"
Pros: "Was upgraded to 1st class, which made all the difference with respect to comfort, food, and service. All were top-notch."
Cons: "old plane, no amenities to make the flight pleasant."
Pros: "Easy, inexpensive flight from Chicago to Mexico City."
Pros: "Staff on board was friendly and professional"
Cons: "Check in counter was closed more than an hour before flight even though electronic tickets weren't working!"
Pros: "The smooth ride and the crew"
Cons: "Waiting for the luggage for so long even though I was flying class premier"
Pros: "The fact that we were served a snack."
Cons: "It took way too long to xheck in."
Pros: "That it took me to my destination"
Cons: "Aeromexico was mediocre with nothing I’d remember about. Food was pretty bad, service kind of rude. The planes were crammed and old. Entertaining also very outdated. The 5 hour layover in Mexico City added unnecessary stress to an already long trip from chicago to Buenos Aires."
Pros: "Punctuality fir boarding, service of crew"
Cons: "The over charge of the 2nd baggage"
Pros: "Flight was smooth"
Cons: "When I first bought the ticket two months ago they rescheduled my departure time. Then two days before my departure they rescheduled my departure time again then when I get to the airport the departure time went 3 hours behind."
Pros: "the worse airline"
Pros: "The flight was not packed and they serves lunch."
Pros: "Nothing it was a very bad experience"
Cons: "Nothing"
Pros: "Service is really good"
Cons: "Food"
Pros: "Checking in was fast and easy"
Cons: "Nothing"
Pros: "On time, courteous service, great movie selection in English and Spanish! Actually served a warm breakfast!"
Cons: "No other open cafes at gate in OHare."
Cons: "Re scheduled 3 different times and flight still arrived 1 hour late."
Cons: "The flight details by the Captain. Came on at the end of the flight"
Pros: "The space on the seats was ok."
Cons: "Food was terrible and not enough on this flight."
Pros: "Flight staff excellent"
Cons: "Seating sucked"
Pros: "On time movies and crew was very nice smooth flight"

All good but wish they had offered ear phones.

This was an excellent flight with very few people on board. Only issue was the 30 minute departure delay and this was communicated well so we weren't left hanging. Traveler communications in Cancun airport aren't the best, but that isn't AC's fault.

Cons: "Took 45 minutes to get through Calgary security, long line ups"
Pros: "I got upgraded to first class!"
Pros: "We had a very good experience with Air canada and will use Air Canada again."
Cons: "Very cramped like sardine tin. Not enough flight info boards in airport and they were hard to read m"
Pros: "Very short flight, not much to say"
Cons: "They airline cancelled our return flight and booked us on another flight more than 2 hours later. We had an event to attend that night so we asked if they could book us on United so we wouldn't miss it. The agent outright lied and said there were no other United flights before then. As we were waiting for our flight, we heard the agents call the final call for a flight to Chicago. Truly disgusted with Air Canada - will never fly them again!"
Pros: "The crew were friendly and efficient."
Cons: "Being delayed for mechanical issues seems to happen more often now, which gives pause. Obviously we want a safe aircraft and I'm glad they deal with the issues, but why are these issues popping up more frequently now? Also, the seats are very uncomfortable for a tall person - no lumbar support"
Cons: "The seats are large, but they tilt forward. I'm 6'2" and have anxiety issues related to spinal problems. That forward pitch in the seat (half way up the seat) is an painful problem for people like me."
Cons: "I could not get a seat assignment or a boarding pass for my connecting flight"
Cons: "Departure was late, causing me to have to run to the next gate"
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."
Cons: "See above."
Pros: "One kind guy at air Canada in Toronto who was very helpful considering the lack of help from every one else. Arrived at 2 in morning exhausted."
Cons: "Attitude of staff"
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: "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: "The flight was on time!!!"
Cons: "I find over the past 25 years that I have been flying with Air Canada the customer service has really went to the dumps !!! Every body is rude and don't understand why."
Cons: "Airline list baggage. Had to wait 3 hours to get luggage which was put it the next flight"
Pros: "Poor airline, always delayed, dreadful and unfriendly customer service. The only reason I flew with them this short trip was due to price"
Cons: "We were in Toronto for an entire week without our bag and Air Canada showed no concern at all for our well being. I travelled with my one year old son, I needed supplies for him and Air Canada gave me dead end numbers to call, websites that didn't work and even hung up on us when we were trying to find out about our bags. They treated us terribly. I will never fly them again."
Pros: "When there were unforseen delays. They just said too bad, here is a phone number you can call. It then took 2 hours to try and get someone on the phone. Once I finally was talking with someone, they said it would cost $200 to rectify the problem. I then got put on hold. When they came back they said it would be over $2000 to get home. Talk about trying to cash is on people's hard situations. I ended up flying WestJet. They were amazing."
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: "horrible"
Pros: "The crew was attentive."
Cons: "The head phone slot did not work. Then the TVs went out which did not matter because I could not listen to them anyway."
Pros: "When I had to reschedule they were very nice about making sure that I had the information I needed and they gave me great seats on the way to London."
Cons: "My flight was Delayed and I had to reschedule that was unfortunate."
Cons: "Delayed"
Pros: "Great Pilots The pilots were great! The weather was not optimal, but they did a great job of making us as comfortable as possible."
Cons: "Better Quality Food Needed The salted plate served was sub-standard. Also, it was full of salt and poses health risk for many people. In the past, better food was served including a pot pie. Also, the staff should be more aware of the wines to be served. And there is not enough attention paid to service in the executive cabin as the attendant runs back and forth between both cabins."
Pros: "Plane was super old...peeling paint, barely any full size luggage space, no in flight tv and always late or delayed. 4/4 flights we took were delayed. This airline is the worst and were terrible at keeping us updated on delays or cancellations."
Pros: "Staff was friendly"
Cons: "Uncomfortable seating"
Cons: "The departure time for the flight was 6:00am and there was no one in the check in counter until 4:15am. There was a long queue for the check in. Not a pleasant waiting time for the check in"
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.""
Pros: "Must bring your own electronic device"
Cons: "The temperature in the cabin was Frigid, even with blanket, 2 pairs of socks my coat & scarf I was freezing!"
Pros: "Quick flight"
Cons: "Delays"
Pros: "Very friendly staff."
Cons: "Left late so missed connection. Was put up in a mediocre hotel."
Cons: "Connecting from London through Toronto to Winnipeg couldn't be accomplished in a 2.25 hr layover. Long line for immigration and and enormous line to go through security again meant I missed my flight and the next one was full. It gave me 5 hours to think of all the reasons why I won't connect through Toronto again."
Cons: "Deplaning and entering the terminal was delayed substantially."
Cons: "No free alcohol. Lights didn't turn off ever so I could get some sleep."
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 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: "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."
Pros: "Organized boarding and in flight service"
Cons: "Late departure"
Pros: "I like having the trip map in front of me so I can track progress. Usually I don't get it on flights this short."
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: "Exceptional ground staff particularly the gentleman who checked me-in in ORD and the German speaking lady in YYZ (gate agent). Also the gate agent in FRA. last but not least, the Very friendly crews on all 3 segments"
Cons: "The food was a bit blend and not worth the calories."
COVID-19 information

Safety measures for airlines flying from Chicago to Winnipeg

Airlines flying from Chicago 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 to Winnipeg

Mandatory masks

Masks required on board, masks provided on flights from Chicago to Winnipeg

Social distancing seating

Middle seats unavailable to book on flights from Chicago to Winnipeg

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago to Winnipeg

Flexible cancellations

Waiving of change fees. Search flexible flights from Chicago to Winnipeg

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26h 10mORD-YWG
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20h 30mYWG-ORD
C$ 309
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15/6Wed
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Chicago - Winnipeg Flights

Departure:

Chicago (ORD)United States

Destination:

Winnipeg (YWG)Canada

Return flight deals:

Winnipeg - Chicago

Cabin classes:

Browse origins:

C$ 309

Browse destinations:

C$ 309