Find cheap flights from Winnipeg to Illinois

Search hundreds of travel sites at once for deals on flights to Illinois

YWG — Illinois
Dec 26 — Jan 21
Round-trip
1 adult
Economy
0 bags
From?
To?
Mon 12/26
Mon 1/2

Let KAYAK do the searching

Save 22% or more

Search hundreds of travel sites at once for deals on flights to Illinois

We’re completely free to use – no hidden charges or fees.

Filter by cabin class, free Wi-Fi and more

Bundle your flight + hotel and save

Latest Illinois Flight Deals

Best round-trip prices found by our users on KAYAK in the last 72 hours

MOST POPULARChicago
1 stop from $281

Good to know

Low season

November

High season

December

Cheapest flight

$157

Average price round-trip

$691

Good deal round-trip

$470

Good deal one-way

$188
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 0% increase in price.
Flight from Winnipeg to Chicago O'Hare Intl
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Winnipeg to the following destinations at these prices or less: Chicago $297 one-way - $399 round-trip
  • High season is considered to be January, February and December. The cheapest month to fly from Winnipeg is January.
  • Morning departure is around 65% 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 - booking Illinois flights

Top 4 airlines serving Winnipeg to Illinois

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 31824 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

Delays really ruin days, excitement, the overall experience of traveling. Having inaccurate times and poor communication sucks.

Read more about Delta

Delays really ruin days, excitement, the overall experience of traveling. Having inaccurate times and poor communication sucks.

Cramped seats. No "food" service due to the short flight. When was the last time real food was served on any domestic flight? Crew not too friendly. Poor sound system to hear the pilot and flight attendants.

Fo

Get the comfort plus! Worth every penny

Thanks

Pros: "Amazing Crew, Entertainment and Comfort."
Cons: "Hot meals served in First Class as opposed to just snacks."
Pros: "Absolutely nothing."
Cons: "Honestly everything."
Pros: "I appreciate that Delta chooses customer safety over profit by not packing flights and continuing to social distance."
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"
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: "Very fast and efficient boarding process. We began moving right when they closed the door. Smooth flight, friendly attendants."
Cons: "Stop charging $2 for headphones lol"
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: "The flight was on time, the crew was pleasant and looked like they enjoyed working in the air."
Cons: "Our second time on a 787 Dreamliner across the Atlantic as about the same as the the first. The seat pitch is very tight so when a passenger reclines into the next row the seatback nearly touches your face. The Dreamliner seats seem to be very hard and it's difficult to get comfortable."
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: "For me the boarding was of fast"
Cons: "The food"
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 crew was attentive."
Cons: "Games on the tv were okay. Tetris would be a nice addition."
Pros: "see above"
Pros: "The service and the crew were extremely courteous polite and professional ."
Cons: "As it is an all flights just not enough leg room and a very tight chair."
Pros: "Flight attendants"
Cons: "Food"
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: "When I went into customer service and explained that I lost my flight because of bean at the immigration for almost 2hrs and the woman she say u going on the next flight, one hr later I was heading to my destination Richmond."
Pros: "Very new plane arrived on time no problems"
Cons: "Nothing everything was great"
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."
Pros: "Being interviewed as I waited in line to check my luggage. Personal touch and felt good safety screening. Bottle of water given out. The friendliness and helpfulness of the crew. I was in the back of the plane. Very cheery despite the masses of people."
Cons: "Seat size small. Although I appreciate the serving of food during the flight, felt a lot of junky carbs and sugar."
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: "Everything was great"
Cons: "Nothing"
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: "We were a little cramped in, but overall it was nice."
Cons: "Not much. It was a quick flight overall."
Pros: "Crew was great. Seats were not comfortable."
Cons: "Slightly wider seats."
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: "Plane was delayed. Wanted to sleep during flight but couldn’t because flight attendants were chatting loudly amongst themselves"
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!"
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: "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: "Fast cheap flight"
Cons: "Nothong"
Pros: "Great crew services, as usual. Nice, smooth flight."
Cons: ""We're waiting for a pilot," doesn't exactly scream, "well oiled machine". How do you rate a bag of pretzels as " Food?""
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: "Wi fi didn't work"
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: "Great crew, West jet connect worked fabulously"
Cons: "Cramped space and airplane food"
Pros: "No stops,"
Cons: "Cramped."
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 crew"
Cons: "Uncomfortable seats and Not enough leg room, especially for tall people. I was in the middle seat and had to basically climg over a sleeping person to get to the washroom"
Pros: "I liked the whole experience.... the crew are always friendly ... they are willing to go that extra mile... I love WestJet as a company and what they stand for... I will not fly any other airline if I have a choice"
Cons: "How misrable people are ... some times I feel for the crew"
Pros: "Overall no issues whatsoever, which is good. Speedy check-in."
Cons: "No luggage space"
Pros: "Nice crew"
Cons: "Nothing"
Pros: "Service"
Cons: "All was as good as expected"
Cons: "Delays"
Cons: "No more seats, rescheduled for the next day. poor service"
Pros: "Staff were pleasant"
Cons: "Flight was rescheduled for 4 times ... Every time standing in a line for the new boarding pass"
Pros: "Business class was comfortable."
Cons: "Flight was delayed 2 hours."
Pros: "The flight was on time and there was adequate foot room"
Cons: "No free snacks- biscuits or pretzels?"
Pros: "The movies on board"
Cons: "The fact the plane was late"
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: "On time, entertainment screen"
Cons: "that there is a charge for headphones"
Pros: "كل شي"
Pros: "Had extra space because plane was not full"
Cons: "Flight was delayed. Changed gate three times"
Pros: "Service flight on time food"
Cons: "No movies for 7 hour flight"
Cons: "no entertainment and poor seat selection"
Pros: "Overall it was a quick and painless flight. The crew was friendly and we had no problems!"
Cons: "First flight was canceled, they did not get me on a flight till 4 pm the next day! Not to mention the two French Canadians I talked to were extremely rude. Finally the 3rd customer service women tried to get me home sooner but was unable to!! Have flown for years on air Canada without issues but this last trip was such an inconvenience I will not being flying with them agin!! They also did not cover my hotel or the taxi costs associated with me having my flight canceled, not even a discount!!!!!"
Cons: "Four hours of delays."
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."
Cons: "The boarding lady on lines 3-5 was rude with several people."
Pros: "The crew was very friendly and attentive."
Cons: "Flight was late so I missed my connection. Then my luggage was delayed by five hours behind me. Generally poor service."
Pros: "Seats were comfortable"
Cons: "35 minute delay in departing. Sat on plane at gate waiting to depart."
Pros: "Fast loading and unloading."
Cons: "Late!"
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."
Pros: "The flight last less time than expected."
Pros: "Nice staff"
Cons: "Not much"
Pros: "Flight was good but there was no tv"
Cons: "There was no TV or to play games"
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"
Pros: "I liked the boarding lines based on groups."
Cons: "Only was offered a small bag of mixed snacks and a drink."
Cons: "Delayed, no food, waiting time to get out of plane too long"
Pros: "Got us home safely. Confortable seats."
Cons: "Left one piece of luggage behind. Had to wait for it to be sent on next flight."
Pros: "More leg room and in flight entertainment."
Cons: "Stewardess spilled hot tea on my husband and did not apologize."
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."
Pros: "Again, nice selection of entertainment and great crew."
Pros: "You want comfort? this is the way to go."
Cons: "Entertainment on short flight was limited."
Cons: "Same movies"
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"
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: "Check in was excellent"
Cons: "Flight was 4 and half hours late for weather and mechanical reasons. Airline responded very well but such a long delay is annoying"
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."
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: "Everithing-----Ramesh"
Cons: "Ramesh"
Pros: "Everything was great"
Pros: "Entertainment system not working for the majority of the flight"
Cons: "Flight was on an older CRJ 200, which was a little cramped and grungy-appearing."
Pros: "Seats were ok."
Cons: "Crew was very grumpy and not accommodating to families (ours and others). No wifi or outlets."
Cons: "The actual flight was fine. It was the delay, followed by what seemed changing info on when it was happening. Every 30 minutes it changed. Five minutes before the flight, the info board said it had been moved to 9:40pm and was changed from Gate 3 to Gate 30, a very long distance to get to. However t"
Cons: "With the exception of delays due to thunderstorms all was excellent."
Cons: "My name was on both reservations, i did not notice this until my wife and i tried to check in. They would not change the name on one of the tickets to my wife, Kathleen. So we had to cancel the entire reservation. I have trip insurance with Allianz, and am trying to get a refund for the tickets. If"
Pros: "Amazing crew"
Cons: "Tight seats, no access to actual WiFi unless you purchase a yearly or monthly plan"
Cons: "Boarding could have been better. If you have 5 groups you should have 5 lines — not 2. Also the terminal in Holland was extraordinarily cold."
Pros: "The crew was very helpful and kind."
Cons: "The entertainment app did not allow me to watch any of the quality programming and my seat to Chicago was extremely cramped and did not recline."
Cons: "Several delays for maintenance and then plane in our gate when we landed"
Pros: "Economy plus was so roomy and the crew was very attentive and nice."
Pros: "On time"
Cons: "Space a little cramped.for spmepne 6'3""
Pros: "Everything was really smooth sailing."
Cons: "Everything was great! The Charleston airport is small yet very nice inside"
Cons: "Charge for baggage. Pretzels - ugh!"
Pros: "Check-in process was smooth"
Pros: "Lots of leg room for a regional jet."
Cons: "AC was not very good. Very warm on flight."
Pros: "The flight was actually with United not Lufthansa."
Cons: "It was like they changed our Lufthansa flight to United. I was not able to get our seat until the last minute at the counter. Luckily the crew was good and helpful atherwise I could not even sit with my husband. My chair was broken so I had to sit very straight. The screen was very tiny like only half size of the one on Luthansa flight. The food was only so so as well but that was just my personal taste."
Cons: "No entertainment on this flight"
Cons: "Delayed due to a late crew member. Arrived 2 hours late into O'Hare making for a very tight connection. Other than the delay, all was fine."
Cons: "Flight attendants seemed completely unwilling to accommodate any requests outside of their "service time"."
Pros: "Staff are so nice"
Pros: "Staff in Syracuse where awsome from the guy at the united check in Guest to the TSA Gal who had to give us a patdown super sweet and helpful."
Cons: "In both airports I was wheeled to gates and left in the way of people coming and going. I tried to get the attention of airline employees and when I did they told someone else and so I sat for between 40-60 minutes."
Pros: "The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something."
Cons: "Delayed for over an hour but not notified of the length of the delay in a fashion which would allow me to drive the 2 hours to Chicago in order to make my connection. Repeatedly told the connecting flight was the last one out of the entire airport to my final destination. Heard other travelers discussing that they had been rebooked onto an alternate airline and then found a later flight on Kayak, walked up to podium and asked to be rebooked on that specific flight, which they grudgingly did. Of note, I was repeatedly reassured that they were "sure" I would make my connection without a problem and to stop worrying so much. My flight left out of Madison 2 minutes after my connection departed Chicago. I usually fly a different airline, whose flights out of Madison were all on time that day, and will do so in the future despite more expensive ticket. The actual crew on the flight was lovely and apologetic, did everything they could to help us despite the delays. At least that's something."
Pros: "Flight was on time and boarding was smooth."
Cons: "The crew weren’t as welcoming. No leg room at all."
Cons: "Extremely small plane. No tv in headrests or on plane, Not enough room for everyone's carry on, no usb charging ports, don't offer unlimited snacks and beverages. They did not offer ANY drinks or snack on this flight which is ridiculous."
Pros: "All went well on on time and service was good."
Pros: "I was impressed that he came into the cabin to talk to us face-to-face instead of just over the intercom. He was friendly and humorous at boarding, and completely serious when he needed to divert. Explained clearly why and kept us informed of next steps."
Cons: "Other than sitting in the airport for 4 hour and changing to 3 different gate and not getting in till 7:30. Need I say more"
Cons: "One of the crew members was late to arrive, so boarding was delayed. However, The gate crew was amazing, very communicative and apologetic. During the flight the attendants seemed very agitated, I think a smile would go along way to improve the attitude of everyone. I also work with the public, I get that it is challenging, but I do believe that the simple gesture of a smile sets the tone."
Pros: "Clean aircraft, swift flight"
Cons: "Seat was changed to last row/middle seat (not what initially booked or confirmed with online check-in). Before takeoff, attendant moved all passengers in back row to alternate seats. Which meant that I was no longer traveling with my colleague. Unfortunately, that made our intended meeting time impossible."
Pros: "United Provide good service"
Cons: "The flight delayed"
Pros: "Very short flight seating was normal for what I expect as a guy my size"
Cons: "I couldnt figure out their wifi to check on my connecting flight. I could get other stuff to work on it but couldnt find flight information"
Pros: "The crews and staff were competent and helpful."
Cons: "The seat pitch and width isn't worth the price of the flight. Some passengers winced some when they saw where they would be seatied in the cramped cabin. For the plane type, I would think not much can be done for the width, but the tight seat pitch is very tight for most of the people that fly."
Cons: "I'm 5'3 and could not even lean forward to rest my head on the table in front of me because there wasn't enough room. I shouldn't have to pay an additional 95 dollars to have what was previously considered a normal seat with normal leg room, especially after loosing 6 hours of my life due to United flight delays during the course of my trip."
Pros: "very kind flight crew, no complaints coming back!"
Cons: "We did have one seemingly annoyed flight attendant on the way to NOLA from Chicago, and older woman. Seemed like every question we had was a burden. Everyone else was really nice, though."
Cons: "My flight to LAX was delayed by over two hours and I had to call and reschedule. I was rescheduled to an AA flight connecting in Chicago. The flight from Chicago to LAX was delayed by over four hours!"
Cons: "I never made it on the flight due to weather conditions they couldn't even hold the flight, and then when I have to get my own accommodations had to pay for my own hotel that is not cool"
Pros: "The staff was friendly and accommodating. The flight was smooth."
Cons: "Nothing"
Pros: "Flight and service were great."
Cons: "United it terrible at letting you know flights are delayed. Got to the airport and found out my flight wasn't going to take off till 2:45 which was 4 hours later then my scheduled flight. I asked the ticketing associate why it was delayed and she said that it was due to crew issues. At least let me know that the flight is delayed so I didn't have to get to the airport 5 hours before my flight took off."
Pros: "Some gate agents were very helpful and friendly with making (gratis) layover changes due to weather issues in my original layover city."
Cons: "They don't assign seats ahead of time, in FCA...too much "juggling" people around prior to boarding."
Pros: "Pilots and some flight attendants were kind and friendly."
Cons: "On the return home, I was seated in the last row right next to the lavatory. I was bumped into at least 25 times by other passengers and flight attendants. I would suggest removing the aisle seat on both sides."
Pros: "Crew was great."
Cons: "Unfortantely their was a mechanical problem that delayed the flight. I understand that failures occur, but only having one mechanic available to work this problem is not good. What happend to the two person concept when working on critical aircraft systems? Pretty hard landing at Chicago."
Pros: "Nothing."
Cons: "No alternative options given. Slow response. No retrieval of email confirmation after purchase of trip. Flight was delayed and no notice was given. Rental car had to ordered last minute and was left without room and board for the night. Had to call again for actual co formation of second flight because no notice was given,"
Cons: "The seats are so narrow in coach that the man with broad shoulders that sat next to me could not help being in my seat. I needed to be able to sleep, since it was an overnight flight. This was not possible."
Pros: "The flight attendents were attentive and did a great job."
Cons: "Customer service was rude to us about our carry on. It was fine on the way to Boston, but made to pay and check it on the way back. other customers had bags our size but we we're rudely told "you need to go pay for your bag that's it". The bag fit effortlessly in the top on the way there."
Pros: "guess that the only thing I liked is that there was no problem during the flight."
Cons: "When we landed un Houston it took forever to get off the plane. It was unclear where to get my luggage. I had to leave it to pass through TSA to run and try to catch my flight from Houston to Chicago. When I arrived at my gate I got there just in time because they were starting to board the plane. I was uconfortable sitting between two men. I traveled alone. When we landed in Chicago, took forever to get to the gate so we can get off the plane. There was no entertainment, at least for me. My phone was way low in battery and ai couldn't watch anything."
Cons: "Delays, had to stay overnight in Chicago since we arrived 6 hours late"
Cons: "For reasons known only to them, United managed to separate the reservations of my wife and mine. Having paid for the trip with the Mileage Plus Explorer card, the first checked bag is free for each traveler. At the kiosk check-in at Logan, the machine wanted to bill us $25 to check my wife's bag. It took another 20 minutes to get this rectified."
Pros: "Crew was very nice."
Cons: "Plane aisle was a tight squeeze with carry on bag plus seats were very close together, and I'm a small person at 5'1". Otherwise flight was good."
Cons: "There was no air circulating on the plane the entire flight. The plane was over 90 degrees when we got on. Everyone on the flight asked for the air to be on and we were told it was. No air was coming out of the vents. Horrible flight."

Book cheap flights from Winnipeg to Illinois

Recent round-trip flight deals

2/12Sun
1 stopMultiple Airlines
9h 15mYWG-MDW
2/15Wed
1 stopMultiple Airlines
9h 00mMDW-YWG
$281
2/12Sun
1 stopMultiple Airlines
8h 14mYWG-ORD
2/15Wed
2 stopsMultiple Airlines
13h 15mORD-YWG
$307
1/27Fri
1 stopDelta
7h 19mYWG-MDW
1/29Sun
2 stopsDelta
12h 57mMDW-YWG
$310
5/12Fri
1 stopMultiple Airlines
9h 32mYWG-MDW
5/15Mon
1 stopMultiple Airlines
7h 35mMDW-YWG
$313
2/12Sun
2 stopsMultiple Airlines
11h 24mYWG-ORD
2/15Wed
2 stopsMultiple Airlines
12h 10mORD-YWG
$313
2/12Sun
2 stopsMultiple Airlines
12h 18mYWG-ORD
2/15Wed
1 stopMultiple Airlines
10h 28mORD-YWG
$325
1/20Fri
1 stopMultiple Airlines
7h 59mYWG-ORD
1/23Mon
1 stopMultiple Airlines
7h 12mORD-YWG
$335
1/20Fri
1 stopMultiple Airlines
7h 59mYWG-ORD
1/23Mon
1 stopMultiple Airlines
7h 12mORD-YWG
$337
5/12Fri
1 stopAir Canada
6h 56mYWG-ORD
5/15Mon
1 stopAir Canada
13h 11mORD-YWG
$339
1/20Fri
1 stopDelta
7h 19mYWG-MDW
1/23Mon
2 stopsDelta
8h 46mMDW-YWG
$340
2/12Sun
1 stopDelta
7h 47mYWG-ORD
2/15Wed
1 stopDelta
9h 07mORD-YWG
$340
2/9Thu
1 stopUnited Airlines
7h 59mYWG-ORD
2/14Tue
1 stopUnited Airlines
13h 35mORD-YWG
$344
2/11Sat
2 stopsDelta
11h 24mYWG-ORD
2/14Tue
1 stopDelta
7h 12mORD-YWG
$370
2/11Sat
2 stopsDelta
11h 24mYWG-ORD
2/14Tue
2 stopsDelta
9h 27mORD-YWG
$375
2/9Thu
1 stopUnited Airlines
8h 10mYWG-ORD
2/18Sat
1 stopUnited Airlines
5h 45mORD-YWG
$431
1/23Mon
1 stopUnited Airlines
7h 59mYWG-ORD
1/23Mon
2 stopsUnited Airlines
17h 15mORD-YWG
$443
2/14Tue
1 stopAir Canada
9h 36mYWG-ORD
2/15Wed
1 stopAir Canada
13h 35mORD-YWG
$455
2/9Thu
1 stopUnited Airlines
6h 51mYWG-ORD
2/12Sun
1 stopUnited Airlines
13h 35mORD-YWG
$461
12/26Mon
1 stopAir Canada
12h 34mYWG-ORD
12/31Sat
1 stopAir Canada
7h 05mORD-YWG
$494
1/20Fri
1 stopEndeavor Airlines
7h 19mYWG-MDW
1/23Mon
2 stopsEndeavor Airlines
11h 57mMDW-YWG
$640

Search by stops

Search by airline

Search by price

Recent one-way flight deals

12/13Tue
2 stopsMultiple Airlines
22h 03mYWG-ORD
$157
12/13Tue
1 stopMultiple Airlines
23h 30mYWG-MDW
$169
12/13Tue
1 stopAir Canada
7h 39mYWG-ORD
$176
12/19Mon
1 stopUnited Airlines
7h 39mYWG-ORD
$180
12/14Wed
2 stopsDelta
12h 15mYWG-ORD
$181
12/19Mon
1 stopMultiple Airlines
15h 26mYWG-MDW
$184
12/13Tue
3 stopsMultiple Airlines
25h 59mYWG-ORD
$190
12/29Thu
1 stopAir Canada
13h 54mYWG-ORD
$196
12/1Thu
1 stopUnited Airlines
7h 39mYWG-ORD
$207
12/13Tue
2 stopsDelta
11h 19mYWG-ORD
$236
12/13Tue
2 stopsDelta
10h 29mYWG-MDW
$243
12/12Mon
2 stopsDelta
9h 40mYWG-ORD
$249
12/1Thu
2 stopsMultiple Airlines
24h 45mYWG-ORD
$252
12/1Thu
1 stopMultiple Airlines
22h 35mYWG-MDW
$253
12/17Sat
2 stopsDelta
9h 39mYWG-ORD
$259
1/20Fri
2 stopsWestJet
11h 39mYWG-ORD
$316
12/26Mon
1 stopAir Canada
12h 05mYWG-ORD
$321
12/29Thu
1 stopUnited Airlines
14h 14mYWG-ORD
$323
12/15Thu
2 stopsWestJet
17h 05mYWG-ORD
$392
12/8Thu
1 stopEndeavor Airlines
11h 26mYWG-MDW
$450

Search by stops

Search by airline

Search by price

Winnipeg - Illinois Flights

Departure:

Winnipeg (YWG)Canada

Return flight deals:

Illinois - Winnipeg

Cabin classes:

$1,059
$1,098
$338

Browse origins:

Browse destinations: