$145 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 2/18. 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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Flight Deals

Cheap Flights from Winnipeg to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$240
St. Louis
St. Louis1 stop$389
Chicago
Chicago1 stop$240
St. Louis
St. Louis1 stop$389

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

Wed, May 20 - Sun, May 24
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 2:30 pm
ORD
-
YWG
21h 00m1 stop
$221WestJet
Thu, Jun 11 - Thu, Jun 18
WestJet Logo
8:30 am - 4:43 pm
YWG
-
ORD
8h 13m1 stop
WestJet Logo
5:30 pm - 11:40 am
ORD
-
YWG
18h 10m1 stop
$233WestJet
Mon, Feb 2 - Mon, Feb 9
WestJet Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
WestJet Logo
2:20 pm - 8:27 am
ORD
-
YWG
18h 07m2 stops
$240WestJet
Fri, Mar 6 - Wed, Mar 11
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m1 stop
Multiple Airlines Logo
7:00 am - 12:41 am
ORD
-
YWG
17h 41m2 stops
$257Multiple Airlines
Sat, Jan 31 - Tue, Feb 3
Multiple Airlines Logo
9:00 pm - 1:37 pm
YWG
-
ORD
16h 37m2 stops
Multiple Airlines Logo
2:53 pm - 3:09 pm
ORD
-
YWG
24h 16m1 stop
$263Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Delta Logo
11:53 am - 4:45 pm
YWG
-
STL
4h 52m1 stop
Delta Logo
6:10 am - 11:03 am
STL
-
YWG
4h 53m1 stop
$389Delta
Sun, Jan 18 - Thu, Jan 22
Delta Logo
6:40 am - 3:00 pm
YWG
-
STL
8h 20m1 stop
Delta Logo
6:10 am - 11:03 am
STL
-
YWG
4h 53m1 stop
$427Delta
Fri, Jan 16 - Sun, Jan 18
United Airlines Logo
5:30 am - 4:03 pm
YWG
-
STL
10h 33m2 stops
United Airlines Logo
4:49 pm - 9:49 am
STL
-
YWG
17h 00m2 stops
$496United Airlines
Sun, Jan 18 - Thu, Jan 22
Air Canada Logo
7:05 am - 3:29 pm
YWG
-
STL
8h 24m1 stop
Air Canada Logo
4:05 pm - 11:54 pm
STL
-
YWG
7h 49m1 stop
$500Air Canada
Fri, Jan 16 - Sun, Jan 18
United Airlines Logo
5:30 am - 3:29 pm
YWG
-
STL
9h 59m1 stop
United Airlines Logo
1:15 pm - 9:49 am
STL
-
YWG
20h 34m2 stops
$527United 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.

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 $308 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 $308.

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 $354 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $602 and $495 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.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$145
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 1% 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 $606 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 $617.

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 $428 one-way - $385 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 9132 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

10.0 ExcellentDr. Joseph, Jan 2026
EWR - ORD
Read more United Airlines reviews

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

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.

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

Information on your arrival and departure airports

Winnipeg (YWG)