$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 5/12. 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
Chicago1 stop$247
St. Louis
St. Louis1 stop$339
Chicago
Chicago1 stop$247
St. Louis
St. Louis1 stop$339

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

ti, elo 25 - la, elo 29
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
$247WestJet
ke, elo 26 - la, elo 29
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
$251WestJet
ti, huhti 28 - pe, Touko 1
Multiple Airlines Logo
9:05 pm - 10:02 am
YWG
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$266Multiple Airlines
ti, huhti 28 - to, huhti 30
Multiple Airlines Logo
9:05 pm - 10:02 am
YWG
-
ORD
12h 57m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$270Multiple Airlines
ke, huhti 15 - ke, huhti 22
Multiple Airlines Logo
7:30 am - 7:31 pm
YWG
-
MDW
12h 01m
1 stop
Multiple Airlines Logo
6:15 am - 3:09 pm
MDW
-
YWG
8h 54m
1 stop
$278Multiple Airlines
ke, huhti 15 - pe, huhti 17
Multiple Airlines Logo
7:30 am - 5:00 pm
YWG
-
ORD
9h 30m
1 stop
Multiple Airlines Logo
2:20 pm - 10:40 pm
ORD
-
YWG
8h 20m
1 stop
$282Multiple Airlines
ma, huhti 13 - ma, huhti 27
Multiple Airlines Logo
8:00 am - 11:17 am
YWG
-
ORD
27h 17m
1 stop
Multiple Airlines Logo
5:50 am - 3:25 pm
ORD
-
YWG
33h 35m
2 stops
$289Multiple Airlines
ti, maalis 17 - ke, maalis 18
Delta Logo
6:40 am - 2:24 pm
YWG
-
STL
7h 44m
1 stop
Delta Logo
3:05 pm - 11:35 pm
STL
-
YWG
8h 30m
1 stop
$339Delta
la, huhti 18 - ti, huhti 21
Delta Logo
5:20 pm - 11:13 pm
YWG
-
STL
5h 53m
1 stop
Delta Logo
6:20 am - 10:56 am
STL
-
YWG
4h 36m
1 stop
$353Delta
la, huhti 18 - ti, huhti 21
Air Canada Logo
5:30 am - 9:52 pm
YWG
-
STL
16h 22m
2 stops
Air Canada Logo
6:30 am - 11:52 am
STL
-
YWG
5h 22m
1 stop
$394Air Canada
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 August.

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 $205 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 $205.

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 $370, 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 February, when the average cost of round-trip tickets is $602 and $546 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, Saturday is the cheapest day to fly and Monday is the most expensive.

Good to know

Low seasonJanuary
Cheapest flight$140
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 3% lower on average.
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 morning, when round-trip flights cost $605 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 $611.

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 $323 one-way - $336 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 9403 reviews
7.1Entertainment
8.1Crew
6.6Food
7.3Comfort
7.7Boarding
Airline reviews

They never clean the toilet, and the food is worse

4.0 OkayAnonymous, Mar 2026
HND - ORD
Read more United Airlines reviews

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

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

Information on your arrival and departure airports