C$ 168 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 21/1. 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, 0 bags

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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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

Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
7:30 a.m. - 10:21 p.m.YWG-MDW
14h 51m1 stop
Multiple Airlines Logo
6:10 a.m. - 3:07 p.m.MDW-YWG
8h 57m1 stop
C$ 303Multiple Airlines
Find Deal
Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
7:30 a.m. - 10:39 p.m.YWG-ORD
15h 09m1 stop
Multiple Airlines Logo
6:20 a.m. - 3:07 p.m.ORD-YWG
8h 47m1 stop
C$ 303Multiple Airlines
Find Deal
Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
4:10 p.m. - 5:41 p.m.YWG-ORD
25h 31m2 stops
Multiple Airlines Logo
6:20 a.m. - 3:07 p.m.ORD-YWG
8h 47m1 stop
C$ 308Multiple Airlines
Find Deal
Fri, 15 May - Wed, 10 Jun
WestJet Logo
8:30 a.m. - 4:43 p.m.YWG-ORD
8h 13m1 stop
WestJet Logo
5:30 p.m. - 11:40 a.m.ORD-YWG
18h 10m1 stop
C$ 315WestJet
Find Deal
Wed, 14 Jan - Mon, 19 Jan
Multiple Airlines Logo
7:30 a.m. - 4:52 p.m.YWG-ORD
9h 22m1 stop
Multiple Airlines Logo
6:20 a.m. - 12:41 a.m.ORD-YWG
18h 21m2 stops
C$ 316Multiple Airlines
Find Deal
Wed, 14 Jan - Mon, 19 Jan
Multiple Airlines Logo
7:30 a.m. - 10:19 p.m.YWG-MDW
14h 49m1 stop
Multiple Airlines Logo
8:28 a.m. - 12:41 a.m.MDW-YWG
16h 13m2 stops
C$ 323Multiple Airlines
Find Deal
Wed, 14 Jan - Mon, 19 Jan
Multiple Airlines Logo
7:30 a.m. - 4:52 p.m.YWG-ORD
9h 22m1 stop
Multiple Airlines Logo
11:48 a.m. - 12:43 a.m.ORD-YWG
12h 55m1 stop
C$ 337Multiple Airlines
Find Deal
Wed, 14 Jan - Mon, 19 Jan
Multiple Airlines Logo
7:30 a.m. - 10:19 p.m.YWG-MDW
14h 49m1 stop
Multiple Airlines Logo
12:57 p.m. - 12:43 a.m.MDW-YWG
11h 46m1 stop
C$ 346Multiple Airlines
Find Deal
Fri, 9 Jan - Fri, 16 Jan
Multiple Airlines Logo
7:30 a.m. - 11:09 p.m.YWG-MDW
15h 39m2 stops
Multiple Airlines Logo
6:10 a.m. - 3:07 p.m.MDW-YWG
8h 57m1 stop
C$ 351Multiple Airlines
Find Deal
Sat, 25 Apr - Thu, 30 Apr
WestJet Logo
4:55 p.m. - 4:43 p.m.YWG-ORD
23h 48m2 stops
WestJet Logo
5:30 p.m. - 10:00 a.m.ORD-YWG
16h 30m1 stop
C$ 387WestJet
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$ 472 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$ 472.

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.

No, with an average price for the route of C$ 538, prices are generally cheapest when you fly direct.

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$ 499 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is C$ 758 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.

Good to know

Low seasonJanuary
Cheapest flightC$ 168
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly (2% 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 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$ 723 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$ 889.

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$ 319 one-way - C$ 851 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 9046 reviews
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
7.7Boarding
Airline reviews

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

10.0 ExcellentJeremy, Nov 2025XNA - ORD
Read more United Airlines reviews

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

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.

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