$187 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 2/10. 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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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$332
St. Louis
St. Louis1 stop$381
Chicago
Chicago1 stop$332
St. Louis
St. Louis1 stop$381

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, Apr 25 - Thu, Apr 30
WestJet Logo
6:55 pm - 4:43 pm
YWG
-
ORD
21h 48m
1 stop
WestJet Logo
5:30 pm - 11:00 pm
ORD
-
YWG
29h 30m
1 stop
$332WestJet
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:55 pm - 4:43 pm
YWG
-
ORD
21h 48m
1 stop
WestJet Logo
5:30 pm - 11:00 pm
ORD
-
YWG
29h 30m
1 stop
$333WestJet
Fri, Apr 17 - Tue, Apr 21
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
Multiple Airlines Logo
5:32 pm - 7:25 pm
ORD
-
YWG
25h 53m
2 stops
$334Multiple Airlines
Sat, Apr 25 - Thu, Apr 30
WestJet Logo
6:55 pm - 4:43 pm
YWG
-
ORD
21h 48m
1 stop
WestJet Logo
5:30 pm - 11:25 am
ORD
-
YWG
17h 55m
2 stops
$339WestJet
Mon, Jun 8 - Thu, Jun 11
WestJet Logo
6:30 am - 4:43 pm
YWG
-
ORD
10h 13m
1 stop
WestJet Logo
5:30 pm - 11:40 am
ORD
-
YWG
18h 10m
1 stop
$346WestJet
Fri, Apr 17 - Tue, Apr 21
Multiple Airlines Logo
6:15 am - 1:35 pm
YWG
-
ORD
7h 20m
1 stop
Multiple Airlines Logo
5:15 am - 12:39 am
ORD
-
YWG
19h 24m
2 stops
$348Multiple Airlines
Wed, Jun 3 - Wed, Jun 10
Air Canada Logo
11:00 am - 8:05 pm
YWG
-
STL
9h 05m
1 stop
Air Canada Logo
7:30 am - 2:23 pm
STL
-
YWG
6h 53m
1 stop
$381Air Canada
Sat, Mar 14 - Fri, Mar 20
Air Canada Logo
7:05 am - 3:29 pm
YWG
-
STL
8h 24m
1 stop
Air Canada Logo
5:00 am - 11:57 am
STL
-
YWG
6h 57m
1 stop
$394Air Canada
Sun, Feb 1 - Thu, Feb 5
Delta Logo
6:40 am - 2:38 pm
YWG
-
STL
7h 58m
1 stop
Delta Logo
6:10 am - 11:03 am
STL
-
YWG
4h 53m
1 stop
$400Delta
Sun, Feb 1 - Thu, Feb 5
Delta Logo
6:40 am - 2:38 pm
YWG
-
STL
7h 58m
1 stop
Delta Logo
6:10 am - 11:03 am
STL
-
YWG
4h 53m
1 stop
$401Delta
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 $191 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 $191.

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 February, when the average cost of round-trip tickets is $602 and $499 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 Wednesday is the most expensive.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$182
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 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 morning, when round-trip flights cost $608 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 $623.

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 9188 reviews
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

Reliable, nice crew, I fly often on that flight and I like it all.

10.0 ExcellentMM, Jan 2026
YVR - ORD
Read more United Airlines reviews

Reliable, nice crew, I fly often on that flight and I like it all.

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

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

Information on your arrival and departure airports

Winnipeg (YWG)