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Find cheap flights from Winnipeg to Chicago

YWG - CHI

Find cheap flights from Winnipeg to Chicago

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Chicago All airports
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Good to know

Low season

January Best time to beat the crowds (17% less expensive on average)

High season

August Most popular time to fly (28% more expensive on average)

Average price round-trip

C$ 554 (avg. price over the last 2 weeks)

Good deal round-trip

C$ 394 or less

When to book flights from Winnipeg to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 503 or less round-trip.
  • The cheapest flight from Winnipeg to Chicago was found, on average, 89 days before departure.
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be July, August and September. The cheapest month to fly is January.

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Top 4 airlines serving Winnipeg to Chicago

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

Pros: "Same crew and great experiments again"
Cons: "Nothing"

Pros: "Kosher snacks! Thank you! Very safe and controlled Covid procedures. Made me feel safe."

Pros: "Very controlled and safe Covid procedures. Outlets and screens at every seat."

Pros: "Felt very clean and so glad they are not selling every seat"

Pros: "great everything!"

Pros: "It was all good glad the last leg of the trip was pleasant."

Pros: "Airplane accelerated from stand-by directly to runway without preparation stop. Awesome!"

Pros: "Nice crew"
Cons: "No leg room for 6’6” person."

Cons: "Small plane, feels cramped"

Pros: "Maria in Winnipeg tried to find me decent connections. She did book me into a hotel in Boston as I missed connection 3 times!!!!"
Cons: "Flights that arrive and leave on time. How can one plan a trip if flights are continually cancelled or delayed. Very frustrating and a very unhappy customer."

Cons: "The unfortunate delay prevented me from attending my grandmother’s wake. Fewer delays would be helpful."

Cons: "No sandwiches for sale just snack boxes"

Pros: "Taco"
Cons: "Taco"

Pros: "The fight was very professionally carried out."
Cons: "The gate agent hurried ineffectively to board our slightly delayed flight (around 10 min). She left open the Priority Lane and boarded all pax there, having to step 4 steps to the left to scan every boarding pass."

Pros: "It was ok"
Cons: "Seat the family together"

Cons: "Taxied at ORD for 45 minutes waiting for a gate to vacate."

Cons: "Smooth on time flight"

Pros: "The crew really kept us updated on the many delays."
Cons: "There were SO many delays and they kept changing. At one point we got on and off the plane."

Pros: "Everything was good except boarding was delayed several times and even after everyone had boarded. We arrived 2 hours behind originally scheduled time as the result."
Cons: "Delta needs to try harder to minimize flight delays."

Pros: "Nothing."
Cons: "Flight was delayed 2 hours. Even though I had carry on, they checked it and this made me waste my time at baggage claim rather than gate checking. Flight attendants were miserable. Power supply didn’t work at seats."

Pros: "The seats were ok."
Cons: "The flight was delayed over 3 hours so I missed my connection in Chicago to Seattle. I’m now stick in Chicago overnight and have to be on a 6 am flight tomorrow. The Delta staff at LaGuaurdia was extremely rude and not helpful at all. Hate Delta......"

Pros: "Flight left on time"
Cons: "Gate crew had trouble identyfing boarding pass on their computer. Difficulty getting on plane"

Pros: "Fast boarding, friendly crew, and comfy seats"
Cons: "It was pretty bumpy and a few times we changed altitude very quickly"

Pros: "I loved the flight attendants and the desk staff everyone was so friendly and made me want to travel delta again."
Cons: "Delta doesn’t offer military spouses free checked bags and I found this out at the airport. It was disheartening, but at least it’s Delta and not the airline that is supposed to represent America."

Pros: "On time"
Cons: "Small aircraft"

Cons: "Over an hour delay before boarding due to supposedly bad weather. Because flight was overbooked they were offering $400 gift card to change to standby on another flight. If you didn’t make that flight (evening), you’d be confirmed on a flight the following morning with one stop in Detroit (we booked a nonstop to Chicago). Uh, no thanks. Then to top it off, we’ve landed and been told that it will be at least an hour before we can deplane due to no availability at the gate (it’s 1145 pm right now). All this plus their new policy of not allowing us to select our seats because we bought the cheapest tickets. Really Delta? You go ahead and cater to the rich and I’ll choose to fly with another airline."

Pros: "Crew friendly"
Cons: "Middle seat with no option for me to move"

Pros: "Friendly service, comfortable seat, on time, no issues."

Cons: "Everything"

Pros: "The crew was great"
Cons: "The flight was 4 hours delayed"

Pros: "I flew on a basic economy fare (I understand the restrictions) and was seated in Economy Comfort +, so that was appreciated."
Cons: "I could see on the Fly Delta app that I had been placed in seat 10B, but neither the app nor my boarding pass gave me a group to board with, so I assumed that I needed to board with group 3, which necessitated gate-checking my rollerboard bag. Only when I approached the gate to board did I notice on the info screen that I had been "upgraded" to Comfort + and granted boarding with the Sky Priority group. I wish this had been clearer so I could have avoided waiting to board and gate-checking my bag. Minor inconvenience but room for improvement on Delta's part."

Pros: "Friendly staff and comfortable seating"

Pros: "This was not my original transfer flight but everyone was much nicer and helpful than serious and being rude. Love Delta, I did not flight United because I wouldn’t have met my United flight once landing in ATL. The Young African American woman who was at the gate was amazing and so reassuring that I would make my flight to Chicago. Would book Delta, just because of how nice she was to me."

Pros: "i liked that staff and crew were very communicative and pleasant."
Cons: "one crew member didn't show up and caused delayed flight."

Pros: "Fast boarding, we even left early! Very kind crew. Flight was WAY shorter than it said on our itinerary!"
Cons: "No TVs and couldn’t get wifi to work. Small plane, slightly uncomfortable."

Cons: "Too tight and seats not comfortable."

Cons: "The delta studio didn't work with Android 8"

Pros: "Ease of flight"
Cons: "N/A"

Pros: "Plane arrived early"
Cons: "They board the front of the plane first, meaning the aisles get clogged up slowing down the process. Also, staff kept insisting pre boarding that more people needed to check their bags because there wasn't enough overhead bin space, but there were plenty of bins not full by take off."

Pros: "Accident on way to airport, so I showed up to check bags 45 minutes before flight time. They said they couldn't get the bag to the plane..in 45 minutes? So, they put on the next flight... 6 hours later. Said I could fly without the bag... uh, no thanks. They would not look for alternatives without charging me more. Flight attendants were crabby, otherwise everything was fine. I flew British Airways a few months ago. Night and day. Seriously. Delta does not even approach having good service. There was no comparison to British Air--- Delta is not in the same league."

Pros: "Airline stewards were very friendly and pleasant."
Cons: "We booked with Delta, but were put on Air France. Even though we had our boarding passes in hand we had to wait in long, slow line for baggage tags because they would not print from kiosk. There was minimal Air France staff on duty serving thousands of passengers during busy season (July). While the lines grew larger, the staff was reduced from 4 to 2. Another long, slow line for customs, another long slow line for security=Charles De Gaulle airport was awful. We arrived at the airport 4 hours before our departure time and got to our boarding gate with no time to spare."

Cons: "Very uncomfortable, seats did not recline and seats way too close together."

Pros: "Entertainment options weren't bad. Most of the crew was polite other than one flight attendant who seemed ambivalent and unhappy to be there."
Cons: "Three hour+ flight and just one tiny bag of pretzels? And no lemon or lime wedges on the beverage cart? Plus, I have to pay extra for one checked bag. I will only fly Delta if I have to in the future. Subpar airline."

Pros: "What I liked: Sky Priority privilege came with separate luggage check-in queues and early boarding"
Cons: "What I disliked: Seats were too small No beverages or snacks offered No USB or power outlets available Three different groups board before Delta Comfort (e.g. those needing more time, travelers with children, first/business class) Didn't see the value compared to a less expensive main cabin ticket"

Pros: "I was notified about the delay via text before I left for the airport, which was nice. I would not have checked my email."
Cons: "Delayed for over 2 hours. I have never flown Delta before this flight and it wasn't a great representation. The flight attendants were nice but I was in a seat near the engine and it was making really weird noises. I fly almost every two weeks, so I'm used to engine noises but this was one of the loudest/most rickety sounding flights I have ever been on.. and I have flown Spirit a few times. It just didn't feel safe. Landing scared me a little too as I have landed in O'Hare countless times and have never flown so low to the highway upon entry. It felt like we were only a couple hundred feet above the cars."

Pros: "Great short trip with an attentive crew."
Cons: "Seats were a bit uncofortable and small compared to previous flights."

Cons: "The flight attendant looked like she was mad throughout the whole flight"

Pros: "We were delayed due to weather and Delta brought a cart of snacks and drinks over to the gate for us."

Pros: "Everything went well"
Cons: "I was late from first flight"

Cons: "Nothing"

Pros: "Fantastic crew!"

Pros: "They were very helpful and polite."
Cons: "Times have changed and they offer very little such as entertainment food options. but it was short trip and people need to adjust."

Pros: "The crew was very nice"
Cons: "Seats are uncomfortable and there’s no tv for entertainment."

Pros: "It booked the wrong date and I had to repurchase the ticket. So all the savings were lost plus a ton more. Last time I use this service."
Cons: "The date and flight I picked were the right ones. I’m sure it was my own fault so it is what it is. I’ll just book through the airlines directly and pay the extra money and ensure the flight is the day I picked."

Pros: "We were a little cramped in, but overall it was nice."
Cons: "Not much. It was a quick flight overall."

Pros: "Average"
Cons: "Two of the most important things to me in travelling by air are getting through security as quick it’s possible ie the priory line; and a lounge. Traveling and paying for Plus provides neither. Back to Air Canada Business Class or AC Rouge Premium. Going to have to pick up your game WestJet"

Cons: "Missed my connection"

Pros: "very organized crew. everything ran soothly and on time. crew was polite to parents with children on board"
Cons: "how quick it was over!"

Cons: "Flight was delayed an hour which isnt horrible but then had to sit on the plane an additional hour waiting for take off. I barely made my connecting flight in Calgary. They should have held that plane because i know the elderlt women next to didnt make it. Staff were not attentive enough. Buzzed them servial times and no response."

Pros: "Easy boarding and checkin."
Cons: "Entertainment doesn't work on laptop - only on phone or tablet. Westjet seating is tight."

Cons: "Early on first flight on arrival but late departing by 30 mins due to westjet delay of crew"

Pros: "West jet staff helpful on plane accommodating my husbands eed for more space."
Cons: "Our seats were pre booked by west jet in a window and center seat my husband is 6’5 and needs to have an aisle seat. We were charged to change these."

Pros: "The trip served its purpose in getting us from point A to B. Good"

Cons: "Plane was delayed. Wanted to sleep during flight but couldn’t because flight attendants were chatting loudly amongst themselves"

Pros: "Great price"

Pros: "Crew and staff are pleasant."
Cons: "There was a typo in my reservation (either a WJ problem or a Kayak problem). As a result I couldn't do an online checkin and ended up getting a middle seat at the airport."

Cons: "no refund at all worst outcome"

Pros: "Airport staff went above and beyond to get my mother through the airport. We had a tight transfer and they helped us make it to the gate on time."
Cons: "There was no time to eat. Nothing other than snacks. The time allotted was *barely* sufficient to get from gate to gate. We were starving when we got to our destination."

Cons: "WestJet seems unable to stick to a schedule. Three of my four flights were delayed and a connector flight through Toronto was cancelled altogether just after midnight, leaving me stranded at Pearson Airport. The ground crew were disorganized and unable to provide clear answers – other than their complete assurance that WestJet bore no responsibility for providing hotel accommodation."

Pros: "Fun crew. Short flight"
Cons: "Flight was late leaving. Our connecting flight was already boarding when we arrived. I would have liked the 25 mins we were supposed to have."

Cons: "I had to travel with a wedding dress. Westjet does will NOT replace lost Wedding dresses therefore they MUST be carried onto the plane. once on the plane there is no where to hang the wedding dress. The flight attendant was kind enough to take it from me and STUFF it in the over head compartment :( I was furious!"

Pros: "The flight staff were very friendly and helpful upon boarding. Once landed even the pilot was standing in view and say good bye. Thanks again!"

Cons: "First flight on WestJet in 3 Years. Didn’t like not knowing I needed a tablet or laptop and an app to watch tv. Offered a drink and asked for water. Received about 2 ounces. Every body around me ordered soft drinks and got a 10 ounce can"

Pros: "Everyone was very nice"
Cons: "It was cold on the plane!"

Cons: "Cramped seating configuration."

Cons: "Thanks"

Cons: "The stewardess (Stephanie was her name I think) grabbed my arm and pushed it out of her way rather than asking me to move. While it may sound dramatic, I am certainly not accustomed to a stranger putting their hands on me and it was hugely inappropriate and ruined my flight. This was my first WestJet flight after flying countless times with Air Canada. The whole experience was soured and I will never look at WestJet the same again."

Pros: "GREAT CREW"
Cons: "BOARDING FROM OUTSIDE-VERY COLD OUT IF I KNEW I WAS BOOKED ON A PROP PLANE I WOULD HAVE BOOKED DIRECT SEAT SIZE-CRAMPPED-I ASK THE GUY BESIDE ME IF HE WANTED THE AILSE BECAUSE HE WAS TALL AND SQUISHED CALL ME ANYTIME 306-551-3251 THAT WAY I WILL KNOW THE VALUE OF THIS SURVEY"

Pros: "The staff and comfort."

Cons: "Overcrowded"

Pros: "Friendly crew and good entertainment"
Cons: "The delay, I don’t know if I’ll be getting a discount or not on a future flight because of it. Original flight was canceled too."

Pros: "West jet employees worked hard to fix the mess they caused. Eventually getting me a ticket for another airline."
Cons: "Changed my flights with less than 3h notice. I’d payed extra to reduce wait times as I was flying with a child just over 2. Originally had me coming in to Vancouver at 9 am and leaving at 5:40pm. Not cool with a young child. Allmost missed the 1st flight getting it fixed, they also didn’t book my child in adjacent seats, despite pre-booking the seats on the flight days before."

Pros: "Quick boarding, good customer service, and friendly staff."
Cons: "When I booked online it was a little unclear that I would have to pay extra to check a bag. No problem but would make a better customer experience if I had been aware of this"

Cons: "Some more food options"

Pros: "Cabin crew was good,"
Cons: "The seats where not compfie"

Pros: "The roominess, service, food.....all excellent"
Cons: "It would have been so much better if there was a foot rest."

Pros: "Again, staff was friendly and approachable attitude."
Cons: "Toronto airport needs proper signage. I got lost and wasted my half an hour to just find a transist to downtown."

Pros: "Pleasant staff"
Cons: "Crowded seating"

Pros: "Comfortable seat with lots of leg room"

Cons: "I was able to download the WestJet Connect app on my phone which gives you access to tv shows and movies to watch on your own device during the flight. The app was free and easy to use and there was a decent selection. However, the wifi on board is not free so even though you could watch the tv show/movie - the sound did not work unless you paid for it. There are many other airlines that offers everything for free - it would have been a more pleasant if we were able to actually utilize the service."

Pros: "The friendliest crew ever!"

Cons: "Hard seats no padding extrely uncomfortable"

Pros: "Great crew, West jet connect worked fabulously"
Cons: "Cramped space and airplane food"

Pros: "No stops,"
Cons: "Cramped."

Pros: "On time"
Cons: "Tight seats"

Pros: "Everything was excelente very nice personal."

Cons: "It was as if the baggage fell of somewhere from the plane and came in contact with water."

Cons: "Flight was late leaving ywg"

Pros: "Awesome crew, chill experience !"

Pros: "Comfortable seat - great service"

Cons: "At the gate, we were told our plane would leave soon. An hour later, they announced the flight was cancelled and we were briskly escorted out of the terminal, told to go through customs and pick up our luggage, which had never even made it on to the plane. They were not re-booking flights at the airport, and the phone lines went to a voice mail message telling us to call back in a few days. I was stranded in Toronto with no phone and no where to stay. It's a week later and I still have not heard anything from from, even though I've called and emailed and sent snail mail."

Pros: "I enjoyed the crew, the food and the entertainment. The crew did give us peanuts for our extra 5 hours on the plane."
Cons: "We were 3 hours late for departure and took 2 extra hours in the air because of re-routing. The seats were abnormally stiff and went back so little that it was extremely hard to fall asleep during the 18 hours we were on board. The crew was unwillng to let us bring our instruments on board and thus, they cracked from the air pressure during the flight."

Pros: "Service flight on time food"
Cons: "No movies for 7 hour flight"

Pros: "Low fare"
Cons: "Flight delayed initially due to weather. When weather cleared flight delayed half hour because they could not find the pilot."

Pros: "Departure was orderly and staff interactions good"

Pros: "Boarding was good, but pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!"
Cons: "Pretty bad flights overall. One of the worst I ever had in my life! The plane seats we had had so little cushion that is was painful to sit. My husband was avoiding touching the back by leaning on his arms and he is great shape, don't think elderly and in pain by himself...Entertainment simply non-existent and food as well... The crew were borderline okay. Plus the plane drove for about 20 minutes at Montreal and about 20 in Chicago before we left and after we landed...Let's say I saw parts of O'Hare in Chicago, I didn't even know existed!!!"

Cons: "no entertainment and poor seat selection"

Pros: "Love the individual entertainment & the friendly staff team"

Pros: "The flight attendant was very nice and smiling."

Pros: "$800 reimbursement 1st class"
Cons: "They overbooked the flight by 2 passengers."

Pros: "service on the plane was good and the crew was very nice to be patient while we boarded the plane with 3 little kids"

Cons: "I arrived at the gate and looked at my ticket to see "GTE" where the seat number usually is. I was informed upon arriving at the desk at the gate that that meant Air Canada has also decided to participate in the ridiculous practice of overbooking their flights and that even though I purchased my ticket roughly 8 weeks prior, there was a chance I might miss my flight to my friend's WEDDING. The lady who was working the desk was as unhelpful and dismissive as you could possibly imagine, refusing to look at me and giving me attitude for merely waiting in the area to see if anyone had missed the flight so I could get on. It was surreal; the only way I could describe her incomprehensible behavior would be to say it was as if her boss were right in front of her and she was trying her damnedest to get fired. It was one of those situations where you could tell this miserable, miserable person was enjoying the power trip she was on and doing everything in her power to make me feel helpless and angry. I made my flight, miraculously, but it was the worst customer service experience I have ever had in my life, airport or not."

Pros: "Great movie selection"
Cons: "Late departing and on arrival the ground crew wasn't available so we were stuck on the plane awaiting their arrival. I can't understand scheduling issues that end up leaving jets stranded."

Pros: "Professional fight attendants, very nice."
Cons: "The flight took off late but most of the lost time was made up during the flight time."

Cons: "Flight was late so I missed my connection. Then my luggage was delayed by five hours behind me. Generally poor service."

Cons: "Flight delayed, service with discrimination, pride, specially male crew, this is a really bad flight experience."

Pros: "Leg room is comfortable"
Cons: "Flight had one and half hour delay. I did not get E-mail reminder for Check-in, for my return flight from Toronto."

Cons: "It was so late, I almost missed my connecting flight. They were not helpful. They did not communicate well and they refused to take any responsibility."

Cons: "Very bad cabin pressure -- lots of ear pain."

Pros: "Again, nice selection of entertainment and great crew."

Cons: "There was some dripping from the ceiling on those of us in the back of the plane. It might have been condensation from the air conditioning or air flow nozzles. In the groove of the ceiling immediately over the seats there seemed to be some dirt or mold."

Pros: "Not much can go wrong on a flight shorter than 90 minutes."
Cons: "3 delays that added up to 1 hr, but counter personnel kept us informed."

Pros: "I . was impressed with the food and service.over all the whole trip was very good"
Cons: "there was nothing I did not like"

Cons: "Moving through security and customs in the Toronto airport was incredibly slow, with 4 or 5 checkpoints, all with lines. Staff were polite but there were not enough of them. We almost missed our connecting flight, and our bags apparently did miss it, because they have not yet arrived in Chicago (see previous comments). Air Canada should have seen the problem in terms of timing with the connecting flight and expedited better. Will try to avoid Air Canada in the future, especially if there are connections in Toronto."

Pros: "All went smoothly"

Pros: "The saftey"
Cons: "Food"

Cons: "if you get in a que, then the computer goes down , your dead, AC line will be 1.5 hours to get to rebook. then you have 2 day to stay before you can get out. if you decide to go on delta because staying 2 day in hotel is more expensive than buying a new ticket ac will not refund you. Air Canada is the least flexible airline in the world relative to refund."

Pros: "Tv in all seats, individual air controls, the crew was nice and I offered up my bag to go on the checked bags when asked and it was the first one out on the bagged claim"
Cons: "I'm 5'8 and my legs hardly fit when sitting straight in the seat"

Pros: "was forced to spend the night in Toronto because Air Canada didn't seem to know that there would be a huge crowd at the airport that evening. I was told as I exited my flight that I would not make the connecting flight and I had to spend the night in Toronto. I will never fly Air Canada again"

Pros: "The crew members in both the flights were amazing. they seemed like they enjoyed their job. Its not very common at Air Canada."
Cons: "The flight from Chicago to Toronto was delayed by half hour. But the boarding gate agents did not even mention the delay."

Cons: "after wetting half hour in the line they said i didn't pay for my ticket and tell me to parches a new ticket"

Pros: "On time or early"

Pros: "It was comfy. Individual screen."
Cons: "We took off 25 minutes late and no food was served, not even a snack. I had to pay 25$ to check in my suitcase."

Cons: "Flight was late"

Pros: "Run by united but more efficient than a recent Air Canada flight."
Cons: "3 hour flight and had to pay extra for entertainment. Only two biscuits given for food. Cramped seats for anyone 6ft tall."

Cons: "I could not check in online for both legs of the flight. Stuck in the middle seat even though I was ready to check in 24 hrs prior."

Pros: "Overall it was good. The crew was very friendly. The plane was small and it was a short flight, so everything else was average as expected for a short flight."

Pros: "The crew was good and the in-flight entertainment options were decent."
Cons: "Plane took forever to take off because we were waiting for people late from layovers. Got one drink, no snacks, nothing else. Plane arrived over an hour late."

Cons: "It was a United flight and everywhere it said it was Air Canada instead of United. Hopping terminals and running through them last minute is not fun. To top it off the flight got delayed a ton of times and messed up our schedules completely."

Pros: "Everithing-----Ramesh"
Cons: "Ramesh"

Pros: "The information screen did not work... Air Canada booth at Winnipeg staff excellent.. Calgary terrible"

Cons: "delayed 2-3 hours in Vancouver so missed connection, had to rent a vehicle to get home. Everytime, United into O'Hare… never again!"

Pros: "Cancellation came with a new flight and coucher for sleeping overnight at a O'Hare Hotel which was very well organized and went smoothly. Staff at ORD were waiting for us and very helpful."
Cons: "Was unable to check in my Air Canada flight the day before to find out the next day, at the airport that the flight was cancelled. The Air Canada flight was operated by United and no such information was provided in my reservation on Kayak or at the Air Canada counter in SAN airport, so I had to guess that another Star Alliance member would be taking over."

Pros: "Everything was great"

Cons: "Gate was changed after check-in, but lack of announcements nearly caused my 84 year old mother to miss her flight, which was changed from gate 80 to 62."

Pros: "Entertainment system not working for the majority of the flight"

Pros: "Great first experience flying."

Pros: "Still able to make it there on the day I needed to be there"
Cons: "Had to be rerouted"

Pros: "The staff was very polite and kind"
Cons: "The ten hour delay"

Cons: "Flight was on an older CRJ 200, which was a little cramped and grungy-appearing."

Cons: "Charge for baggage. Pretzels - ugh!"

Cons: "No entertainment on this flight"

Pros: "All went well on on time and service was good."

Pros: "The staff was friendly and accommodating. The flight was smooth."
Cons: "Nothing"

Cons: "My flight was delayed 9 times with 9 different gate changes. I was supposed to arrive by 10PM and didn't land until 2 AM."

Pros: "Nothing"
Cons: "Flight was delayed. Now have to sleep in airport because connecting flight was missed. Terrible experience."

Pros: "Another flight was issued"
Cons: "My original flight schedule was cancelled"

Pros: "Flights was ontime"
Cons: "Plane was too hot, and then way to cold. This seems to be a re-occurring problem. I am not sure why the plane can't just be set to be be 68-72 degrees. There is no need for it to be above 80 or less than 60."

Cons: "Unable to depart due to pilot wanting windows washed. Created significant delay. Had to rebook flight for next day. Additional cost as a result. I will seek a refund which was due to the delay."

Pros: "It ending"
Cons: "I don't even know where to begin. Horrible flight with two obnoxious dunk clowns that kept this red eye flight awake. Because they were loud and obnoxious they got all the service on the flight. The way they acted, very inappropriately to another passenger, and sneaking booze from their carry on-Wished there was an air marshal on the flight. Won't be flying United again."

Pros: "Crew and workers were all pleasant and polite"
Cons: "United knows they can't fly into Orange County after curfew. This was handled terrible. After 4 delays. All weather related we were finally boarded. Yay hope. Not even to our destination. Boarded to LAX. Now we are seated. The announcement pilots won't fly. No. It is illegal for them to fly. Why not tell customers. Don't blame pilots. Also you know the rules why board us. Even if we flew we still needed a two hour ride to SNA. It was sheer luck I called and was told another flight leaving in 8 min at gate 14 ten gates away. My running to catch that flight was not good. I made it panting. Arrived in LAX at 2:00 a m Not my destination. If nothing else people should be compensated by United don't you think?"

Pros: "Flight on time."
Cons: "Seats uncomfortable"

Pros: "The flight to OHare was fine. No problems whatever. There was no entertainment. The juice was ok."
Cons: "The snack I could not eat for dietary restrictions."

Pros: "Good in flight entertainment"
Cons: "seats were a little less shitty but still shitty"

Pros: "Ive had a hip injury so walking is problematic. I was worried about my 45 minute transfer time in Ohare. The boarding attendant at Charleston ordered a wheelchair to meet me. I got to my plane as it boarded. A distance I couldn't have walked, much less in the time allotted."
Cons: "Not enough time between the two flights for the distance between the two terminals."

Pros: "Excellent service and friendly staff"
Cons: "Absolutely not enough room to stretch your legs"

Pros: "Lots of turbulence"

Pros: "Crew was great"
Cons: "Very complicated boarding. Unpleasant and arrogant gate attendand, she did not show too much of interest in helping us. My husband and I traveled together, but we were seated separately. She changed our seats, but the seats were still not together just in the same row."

Pros: "The O'Hare bathrooms, which I shaved in? Everything else about the flights and the airports were awful, like of course"

Cons: "Delayed three times"

Pros: "Flight was n time, boarding was fast and efficient."

Pros: "Nice plane for a small one"
Cons: "Bumpy ride."

Pros: "Constant updates by email. Very informative"
Cons: "Nothing"

Pros: "The crew was very accommodating during the flight"
Cons: "Delayed over 3 hours, with not much explanation"

Pros: "The crew was very unrespctful spasialy her name is nachelle"

Pros: "Service and crew were excellent. Seats had extra legroom built in."
Cons: "Terrible internet service for the $8.99 I paid. Also the early departure of passengers who have to catch connecting flights doesn't work when those passengers are in window seats. Just get people off the plane and keep passengers from starting conversations with the crew while exiting"

Pros: "My daughter and I sat in Economy Plus which was great because it was towards the front and plenty of leg room. We both have long legs, so this extra comfort made our flight much better and relaxing."
Cons: "One of the Flight Attendants was crabby and unpleasant. This was the first time I've ever had an unpleasant Flight Attendant on a United Flight. I travel quite a bit for business and always try to fly United. I always carry a large purse which always stays on my lap and her and I went back and forth because she insisted that I put it on the floor under the seat. This really upset me."

Pros: "So glad the flight left on time and we actually arrived early!!"
Cons: "'Snacks' were spicy and they should be aware not everyone likes spicy food"

Pros: "On time, boarded quickly, checked my carry on all the way through Tampa for me"

Pros: "Everything was as described"
Cons: "Small plane"

Cons: "A lady with a dog on a leash was allowed on board. I do not think it was a service dog. In the gate area, the dog was encouraged to get up on the seat. The owner also walked the dog over to a couple to visit, and the couple had a large cat in a carrier. The dog owner did not see the cat in the carrier for a few minutes. Then, when she did realized it she did not move away. You could see that the dog noticed the cat and was getting excited, and proceeded to bark. I don't know why she didn't back away when she noticed the cat. On board, the dog, still on a leash, didn't stay under her feet. The owner did not hang on to the leash."

Pros: "smooth sailing the staff was pretty good"

Pros: "Newer plane,"

Pros: "Plane was clean, crew was efficient."
Cons: "Boarding was a nightmare, baggage took 20-30 minutes on the opposite end to be unloaded."

Pros: "They held up connecting flight so that we didn't miss it. We had minimal time to get there because the first flight had to be towed a foot. I really appreciated that"

Cons: "Due to the frequent gate change updates from Kayak we ended up at the wrong terminal. Because of this we were late for our flight which they would not let us get boarding passes for so they bumped us to a flight 2 hrs later. After getting through security we realized the original flight was delayed. We asked the airline if we could get back on that flight and we were rudely told no without a good reason. So we sat for what ended up being and hour looking at the plane we "missed" before it took off. No using United again."

Pros: "Flight was uneventful. Went smoothly."
Cons: "Seating wa very cramped. Long legged people were shoving their knees into my husband's back and I was unable to stretch my legs. Also, there was not a free gluten free snack available."

Cons: "Flight attendants slow to bring drinks around"

Pros: "Crew was very cooperative."
Cons: "Seats were not together we were 3 kids and 2 adults all seats were separate. Crew solve the problem anyway."

Cons: "Seats were not very comfortable."

Pros: "Everything went smoothly"
Cons: "Smoothly and on time"

Cons: "Was told I could sit next to my travel partner but when we went to check in at the boarding gate, we did not have seats together...."

Pros: "Efficient boarding. Ticket price a value."
Cons: "Unfriendly crew. Small, cramped seats. Issues with assigned seats. In-flight entertainment is cost only - i.e. no free option."

Pros: ". We got back 30minutes early then schedule!"

Pros: "left on time without fanfare."
Cons: "internet was weak."

Pros: "Great customer service"

Pros: "I slept during both flights. The connections were close by and I had time to grab a bite to eat."
Cons: "I have no complaints whatsoever. The weather cooperated and the flight crew was super good."

Pros: "Very friendly and great service. Gave us drinks twice."

Pros: "They checked my carry on at the gate in Hartford and said it would go through to me final destination and it wasn't in Cincinnati when I arrived. In fact that was yesterday and I still don't have my luggage."

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Winnipeg to Chicago

Airlines flying from Winnipeg to Chicago 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 Winnipeg to Chicago

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Winnipeg to Chicago

Pre-flight testing

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

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