$126 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 12/10. 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago2 stops$218
St. Louis
St. Louis1 stop$374
Chicago
Chicago2 stops$218
St. Louis
St. Louis1 stop$374

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

Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
12:55 pm - 7:24 pm
YWG
-
MDW
30h 29m2 stops
Multiple Airlines Logo
9:38 am - 3:07 pm
MDW
-
YWG
29h 29m1 stop
$218Multiple Airlines
Sat, Jan 24 - Fri, Jan 30
Multiple Airlines Logo
9:00 pm - 1:37 pm
YWG
-
ORD
16h 37m2 stops
Multiple Airlines Logo
5:40 am - 3:07 pm
ORD
-
YWG
9h 27m1 stop
$233Multiple Airlines
Thu, Jan 29 - Mon, Feb 2
Multiple Airlines Logo
9:00 pm - 10:46 pm
YWG
-
ORD
25h 46m2 stops
Multiple Airlines Logo
9:00 am - 12:36 am
ORD
-
YWG
15h 36m1 stop
$249Multiple Airlines
Mon, Jan 19 - Fri, Jan 23
Multiple Airlines Logo
12:55 pm - 12:05 pm
YWG
-
MDW
23h 10m2 stops
Multiple Airlines Logo
6:20 am - 3:07 pm
MDW
-
YWG
8h 47m1 stop
$253Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
9:00 pm - 1:35 pm
YWG
-
ORD
16h 35m1 stop
Multiple Airlines Logo
6:20 am - 3:07 pm
ORD
-
YWG
8h 47m1 stop
$273Multiple Airlines
Thu, Jan 29 - Mon, Feb 2
WestJet Logo
6:55 pm - 1:35 pm
YWG
-
ORD
18h 40m1 stop
WestJet Logo
2:20 pm - 10:07 am
ORD
-
YWG
19h 47m1 stop
$293WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
9:00 pm - 4:43 pm
YWG
-
ORD
19h 43m1 stop
WestJet Logo
5:30 pm - 10:00 am
ORD
-
YWG
16h 30m1 stop
$298WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
9:00 pm - 4:43 pm
YWG
-
ORD
19h 43m1 stop
WestJet Logo
5:30 pm - 11:40 am
ORD
-
YWG
18h 10m1 stop
$299WestJet
Fri, Mar 6 - Sun, Mar 15
Delta Logo
5:21 pm - 11:23 pm
YWG
-
STL
6h 02m1 stop
Delta Logo
9:30 am - 4:55 pm
STL
-
YWG
7h 25m1 stop
$374Delta
Mon, Jan 26 - Wed, Jan 28
Delta Logo
5:21 pm - 8:52 am
YWG
-
MDW
15h 31m2 stops
Delta Logo
7:16 pm - 11:38 pm
MDW
-
YWG
4h 22m1 stop
$419Delta
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 January.

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 $266 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 $266.

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 $593, 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 $354 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $544 and $473 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 Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Illinois, Thursday is the cheapest day to fly and Wednesday is the most expensive.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$119
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 18% 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 38% 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 $619.

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 $268 one-way - $357 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 9063 reviews
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
Airline reviews

Very bad! They kept delaying my flight and wouldn’t do anything about it

2.0 MediocreSalwa, Dec 2025
DAY - ORD
Read more United Airlines reviews

Very bad! They kept delaying my flight and wouldn’t do anything about it

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)