$189 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 8/31. 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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Cheap Flights from Winnipeg to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$280
St. Louis
St. Louis1 stop$471
Chicago
Chicago1 stop$280
St. Louis
St. Louis1 stop$471

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

Mon, Oct 19 - Thu, Oct 22
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$280WestJet
Thu, Oct 1 - Mon, Oct 5
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$287WestJet
Tue, Sep 29 - Mon, Oct 5
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$297WestJet
Fri, Sep 4 - Sat, Sep 5
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$311WestJet
Tue, Sep 1 - Sat, Sep 5
WestJet Logo
7:00 am - 4:40 pm
YWG
-
ORD
9h 40m
1 stop
WestJet Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$316WestJet
Thu, Sep 24 - Thu, Oct 1
Multiple Airlines Logo
11:15 am - 11:00 am
YWG
-
ORD
23h 45m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$337Multiple Airlines
Tue, Sep 29 - Sun, Oct 4
Multiple Airlines Logo
11:15 am - 11:00 am
YWG
-
ORD
23h 45m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$340Multiple Airlines
Sat, Oct 3 - Wed, Oct 7
Delta Logo
3:58 pm - 11:16 pm
YWG
-
STL
7h 18m
1 stop
Delta Logo
7:10 am - 7:53 pm
STL
-
YWG
12h 43m
2 stops
$471Delta
Sat, Oct 3 - Wed, Oct 7
United Airlines Logo
7:00 am - 12:15 pm
YWG
-
STL
5h 15m
1 stop
United Airlines Logo
6:00 am - 12:37 pm
STL
-
YWG
6h 37m
1 stop
$483United Airlines
Sat, Oct 3 - Wed, Oct 7
United Airlines Logo
7:00 am - 2:16 pm
YWG
-
STL
7h 16m
1 stop
United Airlines Logo
9:04 am - 10:33 pm
STL
-
YWG
13h 29m
1 stop
$484United 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 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 $362 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 $362.

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 $610 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 $648.

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 $362, 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 November, when tickets cost $127 (return) on average. On the other hand, the most expensive months are January and December, when the average cost of round-trip tickets is $447 and $314 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 Saturdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Illinois, Tuesday is the cheapest day to fly and Monday is the most expensive.

Good to know

Low seasonJanuary
Cheapest flight$189
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.
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 $305 one-way - $490 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 9927 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
6.7Food
8.1Crew
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

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

Information on your arrival and departure airports