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Find cheap flights from Winnipeg to Illinois from C$ 211

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Illinois departing on 5/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 7/6
Fri 14/6

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Good to know

Low season

March

High season

August

Cheapest flight

C$ 211
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (16% more expensive on average)
Flight from Winnipeg to Chicago

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Winnipeg to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Illinois from Winnipeg is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Illinois with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Illinois from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 C$ 267 one-way - C$ 669 round-trip
  • Morning departure is around 19% 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

Top 5 airlines serving from Winnipeg to Illinois

 
Need help choosing which airline to fly with from Winnipeg to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.5
Korean AirOverall score based on 1181 reviews
8.6Boarding
8.8Crew
8.3Comfort
8.2Food
8.2Entertainment
Airline reviews

Not very comfortable seated in the back plane due to turbulence

8.0 ExcellentAnonymous, Apr. 2024ICN - ORD
Read more about Korean Air reviews

Not very comfortable seated in the back plane due to turbulence

We were seated at the back and that was very uncomfortable for me with the turbulence we experienced on our way to Chicago.

I enjoyed flying on Korean Air. The service was great and the food was yummy, especially the bibimbap and cold spicy noodles. The only thing that bummed me out on this red-eye flight was that my seat did not properly recline so I was not able to sleep.

Ford not that great the seat not to big for leg room like other airline

Crew was ok, but some passengers were a bit rude. Again, all outlets were not working, only the really slow charging usb plug on the entertainment system. Entertainment system was also bugged, some features just crash, the touch screen wasn't working and when trying to watch a movie the onscreen display kept flashing off and on making it very difficult to watch.

Great crew, decent food Charging plugs were broken on both seats next to me. Only the USB port was available, and that charges, very, very slowly. Seat was also broken, it would not lock into position when reclining.

It was ok. Not good and not a bad experience

not too bad but not too great either. Service on all airlines declined ever since covid. Your Delta Stewardess are not that friendly at all. :-(

I like your stewardess, they are nice. However, your food could have been better and wheres your dessert? You do not offer beer or scotch. I do not drink alcohol biut my husband can have one or two, he has to ask if he can have one. during dinner or lunch, it should be offerred. Also, you do not have the most famous drinks ginger ale

Not accommodating ground staff On board slow service Crew members not very friendly

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Check in was seamless , crew very polite , arrived on time!

Flight arrived early even after leaving late. Bag drop was a zoo, very slow even after using pre-checkin and airport kiosk.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Westjet delayed then rebooked us on flights for economy class when we paid for business class and now need a refund for fare difference and they aren't getting back to us

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

The experience was generally above average. The only downside was the absence of WiFi during my flight from Vancouver to San Francisco.

on demand entertainment in seat back awesome Check in Kiosk too demanding with endless demand for more information information then says go to counter. Counter agent unfriendly. Do it yourself check in luggage procedure not intuitive, upset employees frustrated the whole procedure.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

Touchscreens do not work. WiFi did not work. Food is possibly the worst on any European airline. Drinks came by only four times on a cross-Atlantic. The plane was two hours late because—it was announced—Lufthansa didn't have enough large aircraft in their fleet to accommodate an on-time flight.

The crew member put her luggage and boxes behind my seat so I was able to recline while the passenger in front of me did for 8 hours. My knees were forced against the seat for hours :(. Dude sitting next to me hasn't showered in weeks so I almost threw up.

I always try to book flights that don’t charge for baggage. Yet I was charged $75 for this flight.

Our flight to Chicago O'Hare was delayed an hour, causing us to miss our connection to MSP and spend an extra 3 hours at O'Hare so we could board a plane with a damaged door and wait another 45 minutes or so. The crew was great, the food decent, The drinks were great: 2 glasses of a nice South African Shiraz, an ice cold can of Beck's Beer, and Dewar's White Label on the rocks.

A350 has great entertainment. Make sure to watch the plane's external tail and nose camera's on landing and take off. Seats were a little hard for a 10 hour flight. I am gluten intolerant, they had good alternative meals for me on the flight.

Boarding was horrible. We were packed into a bus with few seats and made to stand for 10 to 15 minutes, then driven for 5 minutes on wild curves. Complementary food and drink was a tiny chocolate and a bottle of water. Seating was cramped. Aircraft had no video.

didn’t even get to go one of my returning flights cancelled and I wasn’t even in their system, vacation ruined thanks for nothing

Need more time for connecting flights in Munich Food seems worse now on Lufthansa Very uncomfortable seats

Better flight than mum to Frankfurt. But food was very mediocre.

Flight landed on time but land services kept us in the plane for 3 hours. I missed connecting flight.

Book cheap flights from Winnipeg to Illinois

Recent round-trip flight deals

18/9Wed
1 stopDelta
6h 07mYWG-MDW
24/9Tue
1 stopDelta
4h 36mMDW-YWG
C$ 405
25/5Sat
2 stopsDelta
9h 18mYWG-MDW
29/5Wed
2 stopsDelta
13h 51mMDW-YWG
C$ 440
18/9Wed
1 stopWestJet
9h 59mYWG-MDW
24/9Tue
2 stopsWestJet
13h 25mMDW-YWG
C$ 468
18/9Wed
2 stopsWestJet
10h 29mYWG-MDW
24/9Tue
2 stopsWestJet
25h 18mMDW-YWG
C$ 477
26/5Sun
1 stop
4h 07mYWG-MDW
28/5Tue
1 stop
22h 53mMDW-YWG
C$ 523
6/6Thu
2 stops
27h 32mYWG-ORD
13/6Thu
1 stop
12h 12mORD-YWG
C$ 529
24/6Mon
directAir Canada
2h 28mYWG-ORD
29/6Sat
1 stopAir Canada
8h 07mORD-YWG
C$ 626
4/6Tue
directAir Canada
2h 28mYWG-ORD
8/6Sat
1 stopAir Canada
11h 40mORD-YWG
C$ 634
8/6Sat
directUnited Airlines
2h 28mYWG-ORD
11/6Tue
1 stopUnited Airlines
7h 10mORD-YWG
C$ 679
4/6Tue
directUnited Airlines
2h 28mYWG-ORD
11/6Tue
1 stopUnited Airlines
7h 10mORD-YWG
C$ 686

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Recent one-way flight deals

5/6Wed
1 stop
12h 47mYWG-ORD
C$ 211
5/6Wed
1 stop
6h 34mYWG-MDW
C$ 229
5/6Wed
2 stops
15h 45mYWG-ORD
C$ 238
5/6Wed
2 stopsDelta
10h 11mYWG-MDW
C$ 266
14/7Sun
1 stopDelta
8h 12mYWG-ORD
C$ 310
14/7Sun
1 stopWestJet
9h 59mYWG-MDW
C$ 359
14/7Sun
1 stopWestJet
9h 59mYWG-MDW
C$ 362
5/6Wed
directUnited Airlines
2h 28mYWG-ORD
C$ 560
8/7Mon
directAir Canada
2h 28mYWG-ORD
C$ 785
14/7Sun
directUnited Airlines
2h 28mYWG-ORD
C$ 974

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Winnipeg - Illinois Flights

Departure:

Winnipeg (YWG)Canada

Return flight deals:

Illinois - Winnipeg

Cabin classes:

C$ 11,494
C$ 2,688
C$ 4,500
C$ 497

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