$173 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 6/8. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$310
St. Louis
St. Louis1 stop$402
Chicago
Chicago1 stop$310
St. Louis
St. Louis1 stop$402

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

Mon, May 25 - Fri, May 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
$310WestJet
Sun, May 3 - Fri, May 8
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
$313WestJet
Fri, May 22 - Sun, May 24
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
$317WestJet
Wed, May 27 - Fri, May 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
$321WestJet
Tue, Sep 8 - Tue, Sep 22
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
$331WestJet
Wed, May 27 - Fri, May 29
Multiple Airlines Logo
9:05 pm - 7:55 am
YWG
-
ORD
34h 50m
2 stops
Multiple Airlines Logo
5:30 pm - 12:55 am
ORD
-
YWG
7h 25m
1 stop
$343Multiple Airlines
Tue, Jun 23 - Tue, Jun 30
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
$345WestJet
Tue, Sep 8 - Mon, Sep 21
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
$346WestJet
Wed, Jun 10 - Sat, Jun 13
Delta Logo
12:46 pm - 6:18 pm
YWG
-
MDW
5h 32m
1 stop
Delta Logo
9:54 am - 3:19 pm
MDW
-
YWG
5h 25m
1 stop
$377Delta
Sat, May 30 - Sat, Jun 6
Delta Logo
6:40 am - 1:19 pm
YWG
-
MDW
6h 39m
1 stop
Delta Logo
7:13 pm - 11:26 pm
MDW
-
YWG
4h 13m
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.

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 May.

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 $297 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 $297.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from Winnipeg to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $599 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 $625.

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 $358 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $652 and $602 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, Wednesday is the cheapest day to fly and Monday is the most expensive.

Good to know

Low seasonMarch
Cheapest flight$173
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Winnipeg to St. Louis

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.

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 $218 one-way - $465 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 9589 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

10.0 ExcellentJim, Apr 2026
BWI - ORD
Read more United Airlines reviews

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

Food and drink service was very low quality. The flight attendants in business class must have been short some staff. Service was sluggish and not much English was spoken

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

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

Information on your arrival and departure airports