$109 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 9/25. 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$199
St. Louis
St. Louis2 stops$432
Chicago
Chicago1 stop$199
St. Louis
St. Louis2 stops$432

Book Cheap Winnipeg to Illinois Plane Tickets

 
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, Oct 17 - Mon, Oct 20
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 9:01 amORD-YWG
15h 31m1 stop
$199WestJet
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Fri, Oct 17 - Mon, Oct 20
WestJet Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:26 amORD-YWG
17h 56m2 stops
$223WestJet
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Sun, Oct 19 - Sun, Nov 2
 Logo
8:30 am - 4:43 pmYWG-ORD
8h 13m1 stop
 Logo
5:11 am - 3:07 pmORD-YWG
9h 56m1 stop
Mon, Oct 27 - Thu, Oct 30
 Logo
9:00 pm - 11:14 amYWG-ORD
14h 14m2 stops
 Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
Tue, Oct 14 - Tue, Oct 21
United Airlines Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
United Airlines Logo
7:54 pm - 10:33 pmORD-YWG
2h 39mnonstop
$336United Airlines
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Tue, Oct 14 - Tue, Oct 21
United Airlines Logo
7:00 am - 9:31 amYWG-ORD
2h 31mnonstop
United Airlines Logo
7:10 am - 1:09 pmORD-YWG
5h 59m1 stop
$345United Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 15
Delta Logo
12:44 pm - 5:35 pmYWG-MDW
4h 51m1 stop
Delta Logo
1:08 pm - 11:27 pmMDW-YWG
10h 19m2 stops
$351Delta
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Wed, Sep 24 - Wed, Oct 1
Air Canada Logo
5:00 am - 10:53 amYWG-ORD
5h 53m1 stop
Air Canada Logo
9:55 am - 5:45 pmORD-YWG
7h 50m1 stop
$358Air Canada
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Fri, Sep 19 - Mon, Sep 29
Air Canada Logo
2:20 pm - 4:51 pmYWG-ORD
2h 31mnonstop
Air Canada Logo
1:01 pm - 3:31 pmORD-YWG
2h 30mnonstop
$390Air Canada
Find Deal
Sat, Oct 25 - Tue, Oct 28
Delta Logo
8:45 am - 8:33 pmYWG-STL
11h 48m2 stops
Delta Logo
6:00 pm - 11:30 amSTL-YWG
17h 30m2 stops
$432Delta
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 $211 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 $211.

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 $453, 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 $395 (return) on average. On the other hand, the most expensive months are April and November, when the average cost of round-trip tickets is $517 and $485 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.

If you are looking for a flight deal from Winnipeg to Illinois, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Illinois, Friday is the cheapest day to fly and Wednesday is the most expensive.

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 the 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 flight$109
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Winnipeg to Chicago O'Hare Airport

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 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 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 $440 on average. Morning departures are around 36% 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 $628.

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 $329 one-way - $369 round-trip

Reviews of the top 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
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
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.

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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