YWG - CHI

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YWG — CHI
20 May — 27 May1
Return
1 adult
Economy
0 bags
From?
To?
Fri 20/5
Fri 27/5

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Good to know

Low season

January

High season

August

Cheapest flight

C$ 247

Average price round-trip

C$ 557

Good deal round-trip

C$ 383

Good deal one-way

C$ 390
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (28% more expensive on average)
Flight from Winnipeg to Chicago
(avg. price over the last 2 weeks)
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When to book flights from Winnipeg to Chicago

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$ 390 or less one-way and C$ 383 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.
  • Morning departure is around 20% more expensive 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 flights from Winnipeg to Chicago

Top 4 airlines serving Winnipeg to Chicago

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 30738 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

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Read more about Delta

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Pros: "Amazing Crew, Entertainment and Comfort."
Cons: "Hot meals served in First Class as opposed to just snacks."
Pros: "Comfortable seats and the plane was not crowded."
Cons: "Wheelchair for my mom was not at the gate in Atlanta, she had to walk and we had to still check immigration, customs and reroute our luggage."
Cons: "The food service on the 3 hour leg but we knew that ahead of time so..."
Cons: "Rude crew. Dirty plane."
Cons: "Better space. Better service. Terrible directions"
Pros: "Nothing."
Cons: "Get us off plane. Been stuck at gate in plane for over an hour."
Cons: "Flight delay"
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."
Pros: "The entire flight was excellent, on time, great friendly crew, edible food, movies and options were great, perfect in every way. It was a little chaotic at flight loading on extra security, but I assume it could have something to do with it being on 9/11 and it was ultimately bound for NYC."
Cons: "I honestly cannot think of anything."
Cons: "No sandwiches for sale just snack boxes"
Pros: "surprisingly spacious seats. plane felt brand new. on screen entertainment was great, and relieved to have charging inputs for my device in the seat."
Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"
Pros: "Customer service on the phone."
Cons: "Delays all day on delta. On my way out and on the return flight."
Pros: "For me the boarding was of fast"
Cons: "The food"
Cons: "I really like more legs room and comfort and crew member were very good and helpful. Regarding food I say it’s just ok."
Cons: "The food not so much breadddd"
Cons: "The delayed at the gate looking for passengers, could have been avoided by doing cross checks at the counter. The snacks need to change. For someone who flies every week like me, the cookies and cheeze it’s get old. Some variety will be awesome."
Cons: "Virgin Atlantic has had better days. Living off of a long gone reputation. Great staff but old and worn out planes. Code sharing has done them no favors!"
Pros: "The two stewardesses were awesome helping me to reschedule possible connecting flight due to leaving mdt 2 hours late"
Cons: "The gate agents were extremely slow causing the flight to pull from the gate 28 minutes late. The capitan of the plane needs a course on how to be polite to an upset customer"
Pros: "The crew was attentive."
Cons: "Games on the tv were okay. Tetris would be a nice addition."
Pros: "see above"
Pros: "Ease of boarding and deboarding"
Cons: "The flight was delayed (naturally) so the crew was rushed and inattentive. No pre-flight beverages in first class, and then no follow up service once aloft unless you asked. Makes me wonder why I’m paying extra for mediocre service."
Pros: "Flight attendants"
Cons: "Food"
Pros: "Very orderly."
Pros: "Snacks and drinks were yummy and very appreciated. Entertainment was great. Tons of shows and movies and all for free. There was also free iMessage only WiFi which was enjoyed while messaging friends and loved ones while in the air."
Cons: "For the amount of passengers boarding, they started the boarding process way too late which resulting in a delay taking off. The entire boarding process felt sloppy, disorganized, and hectic. They allowed passengers to board that were seated at the end of the plane while some 1 was boarding, causing tons of congestion. The boarding process was the slowest I have ever experienced in all the flights I’ve been on. The crew was ok, but slightly snappy/rude like typical New Yorkers. The flight from ft. Lauderdale to New York was much more pleasant."
Cons: "Flight delayed 2 hrs"
Pros: "After almost every airline cancelled. Delta still took me to where I needed to go with not one single problem. That pilot was amazing. I forget his name. But the plane didn't slide or anything during take off. Amazing."
Cons: "What was there not to like. We were a little bit late but I wasn't in a rush. I planned well ahead. Delta moved my flight from 10 a.m. to 6 a.m. and that was perfectly fine with me."
Pros: "My experience with Delta was excellent. Everything from checking in, boarding, flight, and landing was simple. Everyone I came into contact with was extremely helpful and courteous."
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."
Pros: "Was initially hoping to fly a US airline but will now look for Aeromexico first. Exceeded my expectations!"
Cons: "The layover in Mexico City was a bit long and the airport was not so great"
Pros: "Good seat"
Cons: "Delayed by 1 hr"
Pros: "Compared to previous flight - this was so much better with upgrade to first class and extra space."
Pros: "Boarding, checking in etc. The usual stuff, nothign spectacular."
Cons: "Seats are getting too crowded!"
Pros: "Nothing"
Cons: "Delay and inoperative Sattelite TV"
Pros: "The crew was beyond friendly and courteous. Lots of leg room."
Cons: "I was an older plane, it was louder than our flight down to Atlanta. Nothing they could do about it, but a slight annoyance."
Pros: "Smooth flight."
Cons: "I have broad shoulders and there was a larger gentleman on the window seat. Being in the middle seat made for a very very cramped flight the whole way. Lots of skin to skin arm contact for much of the flight. There was no way to avoid it."
Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."
Pros: "Very new plane arrived on time no problems"
Cons: "Nothing everything was great"
Pros: "Entertainment was great. Many options"
Cons: "When we arrived for check in we were told we did not have seats assigned, even though I had picked seats previously. At the gate we were told the flight was very full so we would not be able to sit together."
Pros: "Very professional and caring."
Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."
Cons: "All good"
Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."
Pros: "The two native born Senegalese boys, aged about 8 or 9 were delightful, energetic, generally well behaved."
Cons: "They understood my poor French but I couldn't understand most of theirs. They needed a great deal of help with eating the adult meals they were served and using the entertainment system. At first the flight attendants did little if anything to help. Later after I pointed out the problems we were having they were better. Such young ones needed better supervision and meals easier to eat than they received. I needed less stress on the long 8 hour flight. This was not quite a Sky Priority Comfort Plus experience for me."
Pros: "Love the sofa and cookies."
Cons: "The leg room was reduced to the least I've ever seen on this flight. My knees hit and I'm 5'9'."
Pros: "Always have great experience with Delta flight attendants and staff. The entertainment on mobile phone was a really nice add-on, I had never seen before."
Cons: "Flight was delayed in taking off, waiting for connecting passengers. Plane was old, which is most Delta planes, but this one showed it. The tray table looked like it was from the 70s or 80s. Flying into Midway instead of O'hare was anticlimactic."
Pros: "Smooth flying"
Cons: "The entertainment units were terrible. Touch screens effectively impossible to operate in this 737-800."
Pros: "I liked that I had a vacant seat next to me."
Cons: "Small, narrow seats and way too cramped. Absolutely no leg room or much space to the seat in front. Terrible for a long haul international flight compared to other airlines. No free alcohol on an international flight!"
Pros: "Everything was great"
Cons: "Nothing"
Pros: "The crew was good."
Cons: "Seats where uncomfortable. They didn't have the adjustable padded headrest even though we did coming to Winnipeg. You can no longer change your seat selection 24 hrs before you're flight without a fee. There was also no entertainment coming from Winnipeg even though there was entertainment going to Winnipeg."
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: "Yes"
Pros: "Crew was great. Seats were not comfortable."
Cons: "Slightly wider seats."
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"
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."
Cons: "Early on first flight on arrival but late departing by 30 mins due to westjet delay of crew"
Pros: "The trip served its purpose in getting us from point A to B. Good"
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: "I’ve always liked WestJet and it’s services. They are my always my first airline I go to check flights."
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."
Cons: "Non comfortable cold sensation."
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: "Absolutely nothing."
Cons: "Upon my arrival in Calgary I had missed the last shuttle to Banff (my final destination) and no one at the customer service desk would do anything to help me in my stranded situation."
Pros: "Got away a little late (full flight and de-icing) but still managed to get in to Phoenix well ahead of the scheduled arrival time."
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: "Getting on in Palm springs and getting off in Winnipeg. Thanks WestJet"
Cons: "Not knowing to download The app until I was on the plane"
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"
Cons: "Wi fi didn't work"
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"
Pros: "It was a great flight . It wasn't full so there was a lot of room . It was on time and the Crew was very friendly"
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: "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: "I liked the entertainment application, and the selection of movies. The crew was courteous."
Cons: "The price was high for the calibre of flight, and the luggage overage charges are just silly."
Pros: "Friendly flight attendants and a smooth ride and landing"
Pros: "Got there"
Cons: "Way too expensive"
Cons: "No luggage space"
Pros: "Nice crew"
Cons: "Nothing"
Pros: "Great crew support & well above the typical airline food."
Cons: "USB charging ports would been nice"
Cons: "More drinks, snacks"
Pros: "It was canceled"
Pros: "Comfortable seat - great service"
Cons: "Delays"
Pros: "Crew was friendly"
Cons: "No more seats, rescheduled for the next day. poor service"
Cons: "It’s mainly all good but there are never really snacks on air canada other than pretzels (and today not even that). They are still my fave airline but they could step that up a bit!"
Pros: "The only person who who tried to relax customers waiting to board was the pilot. Flight was delayed. No updates on monitors, no crew at desk. The pilot was first to arrive and had no information but was engaging and joked with all the passengers just standing around. He was our only assurance that flight was still going. He had same attitude on the plane and seemed determined to get us home eventually."
Cons: "No communication from airline. The flight was delayed but we only find out because we show up to gate and nobody is there. No counter agents. When they eventually show up, there is no explanation. Just acted like everything was normal."
Pros: "Size of seats and entertainment"
Cons: "Late leaving, slow baggage claim"
Pros: "Comfortable seats, friendly crew."
Cons: "Almost two hours delay each way."
Pros: "55 minutes before flight, after getting boarding pass they refused to accept baggage. Had to overnight at my expense."
Cons: "Entertainment system didn't work, but only at my seat, after rebooting from electrical problem."
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: "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!!!"
Pros: "Overall it was a quick and painless flight. The crew was friendly and we had no problems!"
Pros: "We landed on time."
Cons: "Flight attendant asked if I needed headphones and I said yes,her reply : I need a credit card"
Pros: "Again, ground crew took good care of me and saw me to the baggage pick-up. You have lovely staff."
Cons: "They didn't have enough room for my carry on so they forced me to hold it on my lap for the entire flight. When I asked if it could be checked, they said no. This was a big safety hazard which shouldn't be overlooked."
Cons: "Four hours of delays."
Pros: "Crew was great and offered a second drink service, which seems rare these days. Food was very tasty, even if I had to buy it myself."
Cons: "We started boarding too early and the service crew had not yet completed their tasks. Thus, we were standing in the jetway, not moving, for about ten minutes."
Cons: "Kiosk option wasn't supporting the baggage check policy, resulting in passenger were unable to print baggage tag and had to wait in long line over 1.5 hrs to check bag with staff. They also understated. It took me over 2 hrs to get throug check in process, not counting 45mins + through security check and custom. I had asked staff to expedite the process. C my flight was boarding. Staff could care or less and walked away. I had to run to my gate and almost miss my flight. Also, I was told that 1st checked bag was complimentary as this is a express aircraft. Staff wouldn't honor that. Come to find out as I entered the aircraft that they made many passengers do the complimentary gate check anyway. Rude and unaccompdating staff."
Pros: "The crew was very friendly and attentive."
Pros: "The entertainment offerings were good. One crew member in particular helped us get back on the flight after we had been booted."
Cons: "Gate agent for Air Canada completely unhelpful about getting us to our connecting flight. Then the Toronto Airport was just HORRIBLE: all along the way, we had to go through security again to get to the American side, and there was no warning that the drinks we had bought *at the Dublin airport* would all be thrown out. Rude security employees. They also very slowly went through the duty free bottles of whisky I bought *at the Dublin airport*. Then there was this stupid line of kiosks that no one knew how to use, then for some reason another boarding check, then another, and then finally customs, with more rude staff members. We had NO IDEA any of this was coming, and got no warning from Air Canada. Then we rushed to our connecting flight, only to find out that we had been booted from the flight anyway. (I got an email about it, which of course I didn't check because I have limited data -- not everyone is made of money who can afford unlimited data!) Then we got on finally boarded, only to sit on the tarmac forever in uncomfortable seats when they could've just let us sit in the airport. Ugh."
Cons: "they made a bunch of people check bags for plane which normally in my past experience has just gate checked larger bags. i'm not sure why they needed to check the bags, and we got away with not having to do that, but it seemed unnecessary"
Pros: "The staff rocked it, despite being in a tough position with grumpy passengers. The desk staff before boarding was less helpful. The seats were comfortable. Entertainment was rated low because it was a short flight it really should have been an N/A because I didn't use it. Not sure how to fairly rate that. No food as far as I could tell."
Cons: "2 hour delay, then sat for another hour or so after being the last to board for fueling and waiting for ground crew."
Pros: "Everything went smoothly. The crew was fabulous and the flight smooth."
Cons: "Not a single complaint from me!"
Cons: "The fact that my ticket said something different from my itinerary and I spent far too long at the counter to get a seat assignment."
Cons: "We were late getting into Chicago and I missed my connection to Albuquerque. I was scheduled to arrive at my destination at noon and because we were late, I didn't get home until almost midnight."
Pros: "entertainment choices"
Cons: "boarding process crew not helpful in baggage storage"
Cons: "The flight left almost 1 hour late because paperwork wasn't signed off"
Pros: "Legroom of seat, on demand and complimentary entertainment system and stable connection of Wifi."
Cons: "Delay of the flight..."
Pros: "One person assisting passengers whose flights had been canceled was gracious and skillful."
Cons: "My flight, 370 was canceled. Initially, one of the AC staff at customer service was overwhelmed and impatient. The next flight was delayed by about seven hours. My baggage didn't arrive in Toronto. I found it extremely difficult to learn where the baggage could be, spent hours on hold with Air Canada and then Dynamex, and waited four days to receive my bag. I was with about 100 people at a summer camp. The staff created a funny skit about AC, Dynamex (sp?) and the endless "your call is important to us" tape recording. I understand that flight plans must be canceled and changed due to weather, but AC relies too heavily on automated "service.""
Pros: "Was arbitrarily assigned a seat with extra legroom. No excessive turbulence; landing was smooth."
Cons: "I was among the last to board and had to place my carry-on under the seat in front because there was no room in the overhead bin. This kept me cramped the entire time despite the "preferred" seating. Soft drink servings were really skimpy."
Cons: "the gate changed FOUR times and passengers were never notified as there were no crew at the gate. The flight was delayed by two hours. there was no in-flight entertainment on board as it wasn't working. upon landing, we were forced to stay in the plane for an extra 30 minutes because the gate and crew were not ready. I was NOT impressed by this flight and am very upset with how things went. I expected better of AC and will not be flying again with them."
Pros: "Nothing, this was the worst flight ever. Delays, no communication, lacked proper updates, ground time,.."
Cons: "Everything, the plane left late. So my bags got lost. The person loading the bags, which I could see from my window, moved at an incredible slow pace and seemed like it took an hour till he was done loading the bags"
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: "You want comfort? this is the way to go."
Cons: "Entertainment on short flight was limited."
Pros: "The pilots always announced when to expect turbulence and apologized ahead of time; turbulence really wasn't that bad either. In-flight entertainment never cut out, though the options were limited."
Cons: "The intercom that the flight attendant used to speak to the passengers was very quiet, so it was hard to hear what he was saying every time. However, the pilots' intercom was very clear."
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: "The female flight attendant was very good at her job."
Cons: "The plane was late out of Toronto making for a mad rush at O'hare to make connection."
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."
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: "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."
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: "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: "Na"
Cons: "Na"
Cons: "Flight was on an older CRJ 200, which was a little cramped and grungy-appearing."
Pros: "The crew was great despite the delay."
Cons: "I choosed this very very expensive flight because it was so import to be home in CPH at 9.00 for an important meeting. My flight from Chicago was delayed and nothing was done by the pilots to arrive on time. Despite the delay, I managed to arrive on time to my Connecting flight to CPH - only to realize that I was moved to a later flight. Now I have spent 2.300 USD on a poor flight that do NOT bring me to my destination on time. I am a frequent flyer, and will do everything I can Avoiding United going forward. Never United again"
Pros: "The check in process at LAX was very efficient and smooth. and the crew on the plane was very considerate. And the tv system on some of the planes is very enjoyable."
Cons: "There was a technical issue on the plane so they had us get off and wait hoping they could fix the problem. It turned into a 3 hour wait. They covered a meal for us which was good and gave us $50 off our next flight. But I’m not sure I want to book united again. The lady at the service desk was not very patient (which is understandable since a loy of people had to rebook their connecting flights). But I was smiling at her and just asking how to go about changing our connecting flights and she seemed a little bit ready to get rid of me. And the next plane we got on, one of our tv screens didn’t work. And the connecting flight was delayed also because of a technical problem."
Cons: "Charge for baggage. Pretzels - ugh!"
Pros: "Efficient crew and easy boarding."
Cons: "No frills but ok."
Cons: "To whom it may concern I had booked flight from Casablanca to Chicago via Frankfurt , on May 6th , by Lufthansa, two hours before the flight , at the counter in CMN , they notified me , that the flight , is over booked , and I can’t catch this flight , and they offered me different difficult options, , till the flight boarded , they offered me one of the most inconvenient flights , and reward me some amount , in this case : I missed my flight which accordingly , lose my appointment , and lose my business. I frustrated with this decision at late hours . I asked full consideration of all the difficulty situation and the turbles they put me ."
Pros: "The leg room and comfort in economy, for a 767, were surprisingly good but the quality of screen and entertainment was lacking. The screen on my iPhone is bigger than the screen on the seatback which if compared to other airlines is not up to the mark. The lack of facilities to charge things like ipads or iPhone was disappointing."
Cons: "The seat comfort was good as was the legroom in economy. The crew were friendly and helpful and I found the overall experience good. If Unitied could build on that and just offer power (even usb) and larger screens they would be onto a winner."
Pros: "Good. Seating. Not too crowded"
Cons: "Na"
Cons: "The TVs were so incredibly small even on Economy Plus, it was almost a joke. Then 1/3 of the flight in my image went white and there were no other open seats to change to. The flight was United, not Luft."
Cons: "No entertainment on this flight"
Cons: "Delays and poor communication. Ended up on other airline and 14 hrs to get from Madison, WI to Baltimore, MD"
Pros: "The flight length and capacity was fine. Crew was nice enough."
Cons: "The plane was outdated, the entertainment was a screen smaller than my phone and had only set movies or shows that played in repeat. Apparently you could download their app and watch other stuff but we weren't informed of that at all while waiting to board which would have been sensible (when there was Wi-Fi access). For a long flight, that would have been nice. They also made a big scene about the bathrooms, apparently us in economy didn't pay enough to use the bathrooms in front of the thin blue curtain that wasn't really closed. It was a bit weird, they're just crappy bathrooms regardless of where they are on the plane."
Pros: "bad movie choices"
Pros: "Nothing"
Cons: "I had to print out my own labels for my bags. No one told me this . Mind you, I was already in line! I had to go print label. Get in line again. Attendant said I need to put the label on myself. And for me to step aside. I was not gonna get out of line again. No one was there to let customers know of this labeling. People were confused! Then I paid $25 online for my luggage. Then my luggage was over 50 pounds. I was charged $100. So I paid $125 for my luggage. Lax TSA Employees are rude and mean. Yelling do this and do that. Like we prisoners. I will never fly United again. I will let everyone know of my experience. Terrible customer service. Then your screens don't work on your airplane. Cannot watch movies. Therefore your plane is not up to par. But I paid up to $700! Never again. Good luck United."
Pros: "Not much to like on United. The boarding was the best part as the staff were somewhat helpful."
Cons: "One nice flight attendant out of the five I interacted with. I'm flying United less and less because the service just sucks."
Cons: "United's In-flight entertainment did not work."
Pros: "The crew from the ticket agents all the way up were great. The app for iPhone is great."
Cons: "I paid for 30 minutes of WiFi to download the United app on my iPad. I wanted to watch the movies/tv shows that were available to passengers. The WiFi was spotty and slow so I wasn’t able to load the app. Needless to say I was disappointed. I also was disappointed with the seating. I am an average size person and I felt very cramped in my seat. My shoulders and neck are killing me after a 2 hour flight. I know that I chose the economy seating but I don’t remember the seats being quite so narrow or the leg room being non existent."
Pros: "Excellent flight"
Cons: "At check in time being told I needed a eta visa to enter Canada!"
Cons: "No reclining seats and no meal. Flew from LAX to CHICAGO. Very uncomfortable. Advertisement for free WiFi on plane, but makes you pay when you log in."
Pros: "The staff all the way through were awesome. Facilities were clean and as expected."
Cons: "Policies about ultra economy tickets sucked. I'm certain I was warned multiple times in the fine print about the hazards of buying a cheap ticket. The fact I was forced to spend money to check a bag and given undo stress about whether or not I'd get bumped because you're not allowed advanced check-in or guaranteed seats with basic economy ticket is not right. Seems the price should simply be the cost to guarantee a basic flight (two carry-on's, guaranteed seat assignment, advanced check-in) so folks can opt out and go for a cheaper ticket on another airline that offer a cheaper fare for the above mentioned guaranteed basic flight options. Felt like a bait and switch."
Pros: "It got us from a to b but not much more to be said!"
Cons: "The idea of the entertainment system broadcast to your hand held device is fine - it didn't work for me though."
Cons: "Confusion and lack of communication about the extra screening process in the airport right before boarding. No information provided ahead of time, to alert me to arrive at the boarding gate early for the extra screening. After I passed through the extra security screening at the gate in Munich, and then went to the counter to complete the extra passport check and security questions, I was asked to step aside and wait. No one told me why. I had to insist on an explanation to the airline staff, and realized there was a mistake - they thought I had not gone through the extra security screening before going to the passport check counter, but I had. This created extra stress and delay for me, as this took place when boarding had started. Respectfully, I suggest that staff is more communicative."
Pros: "Both flight were delayed and I had to reschedule my flights and miss my arrangements."
Cons: "It looks like that there is no respect for Time ."
Pros: "All went well on on time and service was good."
Cons: "Leg I was only offered economy. Not plus"
Pros: "United did a great job keeping us informed of where the plane was and why we were being delayed. Only 15 minutes late. But staff explained why and I think this helps ease people's anxiety. Inflight wifi was awesome!"
Pros: "Easy boarding, room for everything!"
Cons: "On our returning flight, although I'm certain I seated us together, my traveling partner and I weren't seated near each other."
Cons: "Neither my fiancée nor I were particularly fond of the inflight sauna. I had try dry my sweat soaked shirt in the bathroom while waiting to make my connection. If the flight had been any longer I would have opened the door to let a breeze in."
Pros: "I really liked the price for the exact time I wanted to travel!"
Cons: "A bit cramped."
Pros: "We didn't crash?"
Cons: "After much concerns and inquiries made bag did NOT make the plane! There is as no one to h love me to n white Planes for 45 minutes! No one at the counter? Wow! Finally supervisor Jill was able to track it down in Chicago where th y took it off the he plane as my carry on because they had no room l ft from the h limited space. After working very hard to get my bag of o White Plains that evening, supervisor Jill hung out an hour past her shift ended to get it on the last transport to my hotel. The transport blew herself by ft and never showed up or called the o say he wasn't coming back! I got my bag on he next morning just in tim for my event! I also was not credited my frequent flyer miles. Some glitch in the system. Overall I must rate my experience as a one star simply because the pilots got us there safely."
Pros: "The flight attendants were very nice."
Cons: "The seating was a little tight but overall it was a really good flight."
Cons: "Because of a delay in SFO to Chicago O'Hare airport I missed my connecting flight back home. My connecting flight left early without me. While boarding the plane in SFO, the people at the gate made me check my carry on bag. Which I thought was very weird. When we finally got to Chicago I stood in line for two and a half hours to talk to one of the worst customer service lady of my life. She swore at me many times over me trying to be polite and wait for her to call me up to find another flight. Instead she looked at me and said "what are you waiting for?" She said to me "Oh here's a flight. But oh wait it's already sold out or gone" and she would laugh. Finally she found a flight close to where I live. My baggage had got lost from my connecting flight leaving without me. I got all of my luggage 2 days after. My carry on bag that got checked at my gate was in a clear trash bag. I took it out of the bag to find that it was completely trashed. My handles were ripped off which put a huge whole revealing all of my personal items. My carry on bag has only been used once and can never be used again. I unpacked my bag and noticed $300 worth of my stuff was missing. I have called to make many complaints to talk to corporate office but no one would give me the correct number. I will NEVER fly United Airlines again. I am so disappointed."
Cons: "Flights were significanly delayed that resulted in missing connecting flights. During my return trip I ran to make my connecting flight just barely on time and once boarded we sat on the plan for an hour before taking off. Flight to get to Richmond on united was a major problem. I work up with a notification that my flight time had been moved up 2.5 hours ( a problem as I live 2.5 hours away from the airport) I called and they said it was a mistake that I was good to take the origional flight. A few hours later I get a phone call from united asking if I could be at the airport 2.5 hours early. I said unfortunately no because I had already spoken to someone from united and they had reassumed me that the origional flight was still good. She then said if I couldn't make it early it was no problem. So I get to the airport at the origional time after speaking to two different agents who told me this was ok to find the plane delayed and causing me to miss my missed connection."
Pros: "The pilot continued to interrupt our flight home. Watching movies, 4-5 hours his overrides of loud, loud announcement were useless. Trying to take a nap, dark, early evening. We at 29,000 feet, we're ahead of schedule, we are going to arrive 30 minutes early. Then we arrive early sit on the tarmac, because guess what was at our gate; ANOTHER AIRPLANE! All his rushing and interruption were a waste. The ground team had him wait 200 feet away from the gate for another period of time. We arrived three to five minutes early, at 7:30 PM. Very unpleasant flight."
Pros: "I think these older flight attendants should retire if they don't like their jobs anymore. They were completely rude to many guest."
Pros: "At least I made it"
Cons: "Flight attendant for United 426 to Chicago was rude, flight delayed and they weren't very helpful"
Cons: "It was so late it left me in the lurch and ruined my week"
Cons: "I was on a super late flight to Chicago and for some reason was placed in Boarding Group 5 (I have a United cc, so I thought that came with the perks). I got over that part. But then they made me check my roller-board claiming they were full up. When I boarded, there was PLENTY of overhead bin space. So I had to go to baggage claim after midnight for no reason. Bummer."
Pros: "Nothing much"
Cons: "Your refund or rescheduling policies."
Cons: "Somehow I ended up with a middle seat all three flights I took. I would have upgraded if offered. Plane wasn't all that comfortable. All and all, you guys got me where I needed to go, so I can't really complain. Thank you"
Pros: "The staff was friendly and accommodating. The flight was smooth."
Cons: "Nothing"
Cons: "No free wifi. No free entertainment. Smaller than a kids small fruit snack bag of trail mix for a 4+ hour flight. Gate issues delaying our boarding-resulting in late take off.- and delayed transit home to last available route of the night- thank goodness!"
Pros: "We didn't crash"
Cons: "The gate attendant reopened the plane for the man in front of me because he had one book bag and refused to let me on because I had two. The room and taxi voucher were adequate. But $30 in food vouchers doesn't get you very far in an airport. Also that's just enough to survive the lay over that was caused by your maintenance issues. Your attendant then tried to put me on standby all day the following day with a guaranteed flight at 8pm. I then asked him to check other airlines and was able to get an 8am one. The sheer lack of customer service is impressive. PS if your airline screws up, the least I deserve is a seat upgrade or some free sky mile points."
Pros: "NOTHING."
Cons: "We had a confirmed reservation on tickets that I bought months ago. However, when we went to get our seats, the flight had been oversold. We were involuntarily booted off the flight- even though one on standby got a seat, and another person did not show up- we could have gotten on the flight! We were heavily compensated and the staff were as generous as they could be, but it was completely frustrating and upsetting when you have to go through that, after ahead time planning to be booted off a flight like that."
Pros: "I liked the staff. Everyone was nice and hospitable."
Cons: "The ride was a bit bumpy, but sometimes that's uncontrollable."
Pros: "Nice CSR people in AZO"
Cons: "United delayed the flight. This information became available about an hour in advance- well after we drove two hours (We live in Montana) to get to the airport. The attendants said / not our problem. I called United's Customer Service number to discuss ways of mediating the delay that resulted in us missing the wedding venue and entire reason we booked the $1400 flight. I again got a "not my problem" response- no the flights can be modified, no we will not provide vouchers, no we really don't care that our poor quality and service cost you and your family tremendously in time, effort, and lost memories. I know we are at the mercy of airlines, but what a painful disappointment. My experience with Delta has been better and I suggest avoiding United Airlines if other flight options exist.... Even consider a very long drive over the use of the airline."
Cons: "Where do I start. Let's start with booking and the lack of knowledge, inability to listen and respond in an appropriate manner, and the fact that after I asked to speak to a manager due to the previous issues with the agent, and after being transferred all I needed was some understanding and support due to a family emergency and instead I get a short rude push back and then hung up on by the manager after I expressed my struggle and desperation for help. The lack of empathy and just the overall experience was beyond horrible, and if it wasn't for the desperate situation I was in I would have never used your services."
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

Flexible cancellations

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

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