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$166 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 9/21. 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

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Flight Deals

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

Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
11:15 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 9:45 amMDW  Chicago Midway-YWG Winnipeg
22h 00m1 stop Toronto Island
$320Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
8:45 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
14h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 9:45 amMDW  Chicago Midway-YWG Winnipeg
22h 00m1 stop Toronto Island
$328Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
11:15 am - 2:35 pmYWG  Winnipeg-MDW Chicago Midway
27h 20m2 stops Montreal St Hubert Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 8:40 amMDW  Chicago Midway-YWG Winnipeg
20h 55m1 stop Toronto Island
$331Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
8:45 pm - 2:35 pmYWG  Winnipeg-MDW Chicago Midway
17h 50m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 9:45 amMDW  Chicago Midway-YWG Winnipeg
22h 00m1 stop Toronto Island
$338Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
Multiple Airlines Logo
8:45 pm - 2:35 pmYWG  Winnipeg-MDW Chicago Midway
17h 50m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 8:40 amMDW  Chicago Midway-YWG Winnipeg
20h 55m1 stop Toronto Island
$339Multiple Airlines
Thu, Sep 10 - Sun, Sep 13
WestJet Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$351WestJet
Wed, Sep 2 - Sat, Sep 5
WestJet Logo
4:55 pm - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
23h 45m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$357WestJet
Wed, Sep 2 - Sat, Sep 5
WestJet Logo
7:00 am - 4:40 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
9h 40m1 stop Calgary
WestJet Logo
5:30 pm - 12:55 amORD  Chicago O'Hare Intl-YWG Winnipeg
7h 25m1 stop Calgary
$358WestJet
Wed, Sep 23 - Fri, Sep 25
United Airlines Logo
5:00 am - 9:59 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
16h 59m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
United Airlines Logo
9:25 pm - 4:27 pmORD  Chicago O'Hare Intl-YWG Winnipeg
19h 02m2 stops Nashville Intl Toronto Pearson Intl
$618United Airlines
Wed, Oct 7 - Wed, Oct 14
United Airlines Logo
5:10 am - 6:30 pmYWG  Winnipeg-ORD Chicago O'Hare Intl
13h 20m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
United Airlines Logo
6:03 pm - 2:22 pmORD  Chicago O'Hare Intl-YWG Winnipeg
20h 19m2 stops Atlanta Hartsfield-Jackson Toronto Pearson Intl
$667United Airlines
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 September.

Flight prices are below average for this route right now.

Flights to Illinois from Winnipeg usually cost between $509 and $692 in September.
The lowest price found in the past 5 days was $351 on WestJet (Sep 10-Sep 13).

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 $306 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 $306.

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 afternoon, when round-trip flights cost $630 on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $655.

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 $448 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 $380 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $692 and $666 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 Tuesday, as it's usually the priciest day. When flying back from Illinois, Tuesday is the cheapest day to fly and Wednesday is the most expensive.

Find deals

Good to know

Low season

January

Cheapest flight

$166
Best time to beat the crowds but there is an average 55% increase in price.
Most popular time to fly with an average 10% 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.

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 $384 one-way - $551 round-trip

Reviews of the top airline 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 10104 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.7Food
Airline reviews

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

2.0 MediocreGreg, Jun 2026
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

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

Information on your arrival and departure airports

Winnipeg (YWG)