C$ 275 Find Cheap Flights from Winnipeg to Illinois – Compare and Save

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 12/8. 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Thu, 1 Oct - Tue, 6 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 422WestJet
Thu, 24 Sep - Sun, 27 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 424WestJet
Tue, 29 Sep - Sun, 4 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 436WestJet
Fri, 25 Sep - Thu, 1 Oct
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 5:25 p.m.
ORD
-
YWG
23h 55m
1 stop
C$ 454WestJet
Fri, 4 Sep - Sun, 6 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 474WestJet
Fri, 30 Oct - Sun, 1 Nov
WestJet Logo
6:15 a.m. - 1:35 p.m.
YWG
-
ORD
7h 20m
1 stop
WestJet Logo
2:20 p.m. - 9:40 p.m.
ORD
-
YWG
7h 20m
1 stop
C$ 475WestJet
Thu, 1 Oct - Sun, 4 Oct
WestJet Logo
4:55 p.m. - 4:40 p.m.
YWG
-
ORD
23h 45m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 478WestJet
Tue, 29 Sep - Fri, 2 Oct
Multiple Airlines Logo
11:15 a.m. - 11:00 a.m.
YWG
-
ORD
23h 45m
2 stops
Multiple Airlines Logo
7:00 a.m. - 8:30 p.m.
ORD
-
YWG
13h 30m
1 stop
C$ 481Multiple Airlines
Mon, 21 Sep - Tue, 22 Sep
WestJet Logo
7:00 a.m. - 4:40 p.m.
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:55 a.m.
ORD
-
YWG
7h 25m
1 stop
C$ 485WestJet
Tue, 15 Sep - Sat, 19 Sep
Delta Logo
5:44 p.m. - 9:07 a.m.
YWG
-
MDW
15h 23m
2 stops
Delta Logo
4:30 p.m. - 3:08 p.m.
MDW
-
YWG
22h 38m
2 stops
C$ 731Delta
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.

How much is a round-trip flight from Winnipeg to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Winnipeg to Illinois departing in October.

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 5 days was to Chicago, at C$ 552 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 5 days was C$ 552.

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

The average price for all round-trip flights from Winnipeg to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost C$ 884 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$ 1,007.

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$ 611 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 November, when tickets cost C$ 180 (return) on average. On the other hand, the most expensive months are January and December, when the average cost of round-trip tickets is C$ 634 and C$ 446 respectively.

Good to know

Low seasonJanuary
Best time to beat the crowds but there is an average 61% increase in price.
Most popular time to fly and prices are also 23% lower on average.

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.

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$ 606 one-way - C$ 774 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 9900 reviews
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

2.0 MediocreGreg, Jun 2026
YYZ - ORD
Read more United Airlines reviews

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Reliable, nice crew, I fly often on that flight and I like it all.

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

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

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

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.

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Very good over all , would have been nice to have entertainment on the flight

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

The flight itself was fine, but two of the ladies at the gate were extremely rude to a few of us in line. Their customer service really needs some help. I’ve always had good experiences with WestJet until these two ladies. They had the worst attitudes and really left a bad taste in my mouth after a good trip

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Flight got cancelled. I had to spend many hours on phone to have it rescheduled at my convenience

I like the fact air Canada is on time The food you guys serve is not good

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

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

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

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

It was swiss air flight and they were very helpful and kind

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

Information on your arrival and departure airports