C$ 187 Find Cheap Flights from Winnipeg to Illinois

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 2/10. 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
1 adult, Economy

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Winnipeg to Illinois, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Winnipeg to Illinois

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Illinois

Tue, 30 Sep - Sat, 4 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 238WestJet
Find Deal
Mon, 24 Nov - Fri, 28 Nov
WestJet Logo
6:15 a.m. - 1:35 p.m.YWG-ORD
7h 20m1 stop
WestJet Logo
2:20 p.m. - 10:41 p.m.ORD-YWG
8h 21m1 stop
C$ 254WestJet
Find Deal
Tue, 30 Sep - Mon, 6 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 9:01 a.m.ORD-YWG
15h 31m1 stop
C$ 294WestJet
Find Deal
Mon, 29 Sep - Sat, 4 Oct
 Logo
9:00 a.m. - 5:26 p.m.YWG-ORD
8h 26m1 stop
 Logo
1:40 p.m. - 9:25 p.m.ORD-YWG
7h 45m1 stop
C$ 295
Find Deal
Tue, 30 Sep - Sat, 4 Oct
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
1:40 p.m. - 11:10 p.m.ORD-YWG
9h 30m2 stops
C$ 302WestJet
Find Deal
Sun, 19 Oct - Sun, 2 Nov
 Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
 Logo
5:11 a.m. - 3:07 p.m.ORD-YWG
9h 56m1 stop
C$ 326
Find Deal
Tue, 14 Oct - Tue, 21 Oct
United Airlines Logo
2:20 p.m. - 4:51 p.m.YWG-ORD
2h 31mdirect
United Airlines Logo
7:54 p.m. - 10:33 p.m.ORD-YWG
2h 39mdirect
C$ 462United Airlines
Find Deal
Tue, 14 Oct - Tue, 21 Oct
United Airlines Logo
7:00 a.m. - 9:31 a.m.YWG-ORD
2h 31mdirect
United Airlines Logo
7:10 a.m. - 1:09 p.m.ORD-YWG
5h 59m1 stop
C$ 474United Airlines
Find Deal
Wed, 1 Oct - Wed, 15 Oct
Delta Logo
12:44 p.m. - 5:35 p.m.YWG-MDW
4h 51m1 stop
Delta Logo
1:08 p.m. - 11:27 p.m.MDW-YWG
10h 19m2 stops
C$ 482Delta
Find Deal
Tue, 30 Sep - Thu, 2 Oct
Delta Logo
6:40 a.m. - 12:28 p.m.YWG-MDW
5h 48m2 stops
Delta Logo
9:35 a.m. - 8:11 p.m.MDW-YWG
10h 36m2 stops
C$ 495Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Winnipeg to Illinois flights

Get data-powered insights and trends into flights from Winnipeg to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Winnipeg to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Winnipeg found in the last 72 hours was to Chicago, at C$ 341 round-trip. The most popular route is from Winnipeg (YWG) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was C$ 341.

Can I save money by flying with a layover from Winnipeg to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at C$ 596 on average.

What is the cheapest month to fly from Winnipeg to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Winnipeg to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Winnipeg to Illinois is September, when tickets cost C$ 543 (return) on average. On the other hand, the most expensive months are April and November, when the average cost of round-trip tickets is C$ 710 and C$ 667 respectively.

What’s the cheapest day of the week to fly from Winnipeg to Illinois?

The average price of all round-trip flights from Winnipeg to Illinois clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Illinois on a Wednesday and more expensive on a Sunday. On your return trip to Winnipeg, you should consider flying back on a Tuesday, and avoid Wednesdays for better deals.

How far in advance should I book a flight from Winnipeg to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Winnipeg to Illinois, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Winnipeg to Illinois, you should book around 7 weeks before departure, which saves you about 58% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flightC$ 187
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 0% lower 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 from Winnipeg to Illinois is likely to change within 7 days, so travellers 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 from Winnipeg to Illinois with an airline and back 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 from Winnipeg to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost C$ 512 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is C$ 625.

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$ 582 one-way - C$ 548 round-trip

Reviews of the top 3 airlines flying from Winnipeg to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Winnipeg to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.4
United AirlinesOverall score based on 8941 reviews
7.3Comfort
7.7Boarding
6.6Food
7.1Entertainment
8.1Crew
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

Seat back entertainment monitors would be nice. We did enjoy the In-Flight WiFi.

Upgraded to sit at the exit door so good leg room.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

Everything you need to know for your flight from Winnipeg to Illinois

Information on your arrival and departure airports

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