$140 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 1/30. 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$209
St. Louis
St. Louis1 stop$348
Chicago
Chicago2 stops$209
St. Louis
St. Louis1 stop$348

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, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
9:00 pm - 7:42 pmYWG-MDW
22h 42m2 stops
Multiple Airlines Logo
6:15 am - 3:07 pmMDW-YWG
8h 52m1 stop
$209Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
9:00 pm - 10:12 pmYWG-MDW
25h 12m2 stops
Multiple Airlines Logo
6:15 am - 3:07 pmMDW-YWG
8h 52m1 stop
$217Multiple Airlines
Find Deal
Fri, Jan 16 - Mon, Jan 19
WestJet Logo
6:15 am - 1:35 pmYWG-ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 10:41 pmORD-YWG
8h 21m1 stop
$238WestJet
Find Deal
Thu, Feb 12 - Mon, Feb 16
WestJet Logo
9:00 pm - 1:35 pmYWG-ORD
16h 35m1 stop
WestJet Logo
2:20 pm - 10:40 pmORD-YWG
8h 20m1 stop
$268WestJet
Find Deal
Tue, Apr 14 - Wed, Apr 15
United Airlines Logo
8:30 am - 8:59 pmYWG-STL
12h 29m1 stop
United Airlines Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$348United Airlines
Find Deal
Mon, Dec 15 - Mon, Dec 22
Delta Logo
5:45 pm - 11:29 pmYWG-STL
5h 44m1 stop
Delta Logo
7:06 pm - 11:44 pmSTL-YWG
4h 38m1 stop
$349Delta
Find Deal
Tue, Apr 14 - Wed, Apr 15
United Airlines Logo
8:30 am - 8:59 pmYWG-STL
12h 29m1 stop
United Airlines Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$350United Airlines
Find Deal
Tue, Apr 14 - Wed, Apr 15
Air Canada Logo
7:15 am - 3:21 pmYWG-STL
8h 06m2 stops
Air Canada Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$407Air Canada
Find Deal
Tue, Apr 14 - Wed, Apr 15
Air Canada Logo
6:00 am - 3:21 pmYWG-STL
9h 21m2 stops
Air Canada Logo
1:30 pm - 8:48 pmSTL-YWG
7h 18m1 stop
$463Air Canada
Find Deal
Tue, Mar 3 - Sun, Mar 8
Delta Logo
6:35 am - 1:09 pmYWG-MDW
6h 34m1 stop
Delta Logo
6:00 am - 3:09 pmMDW-YWG
9h 09m1 stop
$548Delta
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 $359 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 $359.

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 $491, 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 $483 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 Fridays 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.

Good to know

Low seasonJanuary
Cheapest flight$140
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Winnipeg to Chicago Midway 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 $618.

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 - $482 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 8997 reviews
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
Airline reviews

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.

10.0 ExcellentDr. Joseph, Oct 2025STL - ORD
Read more United Airlines reviews

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.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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

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