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Find cheap flights from Winnipeg to Illinois from $145

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 6/1. 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
0 bags
Sun 6/16
Sun 6/23

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Best Illinois Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicago1 stop$267
St. Louis
St. Louis3 stops$465

Good to know

Low season

March

High season

August

Cheapest flight

$145
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 16% increase in price.
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 to Illinois from Winnipeg 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 to Illinois with an airline and back to Winnipeg 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 to Illinois from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $571 one-way - $414 round-trip
  • Morning departure is around 15% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Winnipeg to Illinois

 
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.
8.5
Korean AirOverall score based on 1171 reviews
8.6Boarding
8.3Comfort
8.1Food
8.2Entertainment
8.8Crew
Airline reviews

Not very comfortable seated in the back plane due to turbulence

8.0 ExcellentAnonymous, Apr 2024ICN - ORD
Read more about Korean Air reviews

Not very comfortable seated in the back plane due to turbulence

We were seated at the back and that was very uncomfortable for me with the turbulence we experienced on our way to Chicago.

I enjoyed flying on Korean Air. The service was great and the food was yummy, especially the bibimbap and cold spicy noodles. The only thing that bummed me out on this red-eye flight was that my seat did not properly recline so I was not able to sleep.

Ford not that great the seat not to big for leg room like other airline

Crew was ok, but some passengers were a bit rude. Again, all outlets were not working, only the really slow charging usb plug on the entertainment system. Entertainment system was also bugged, some features just crash, the touch screen wasn't working and when trying to watch a movie the onscreen display kept flashing off and on making it very difficult to watch.

Great crew, decent food Charging plugs were broken on both seats next to me. Only the USB port was available, and that charges, very, very slowly. Seat was also broken, it would not lock into position when reclining.

It was ok. Not good and not a bad experience

not too bad but not too great either. Service on all airlines declined ever since covid. Your Delta Stewardess are not that friendly at all. :-(

I like your stewardess, they are nice. However, your food could have been better and wheres your dessert? You do not offer beer or scotch. I do not drink alcohol biut my husband can have one or two, he has to ask if he can have one. during dinner or lunch, it should be offerred. Also, you do not have the most famous drinks ginger ale

Not accommodating ground staff On board slow service Crew members not very friendly

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Check in was seamless , crew very polite , arrived on time!

Flight arrived early even after leaving late. Bag drop was a zoo, very slow even after using pre-checkin and airport kiosk.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Seriously need to improve the time schedule and the plans

Great TV, easy boarding, wonderful ground crew and flight crew.

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Overall, I would have to say my experience with Air Canada was mediocre their DC tens. Need to be updated not comfortable at all. Only one out of my four flights was decent. The staffing was very nice. Going through customs in Montreal was quick and easy. Air Canada has room for improvement with their facilities.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

Book cheap flights from Winnipeg to Illinois

Recent round-trip flight deals

5/27Mon
1 stopWestJet
8h 35mYWG-ORD
6/1Sat
1 stopWestJet
17h 47mORD-YWG
$267
6/15Sat
1 stopDelta
8h 10mYWG-ORD
6/22Sat
2 stopsDelta
10h 04mORD-YWG
$282
6/13Thu
1 stop
12h 47mYWG-ORD
6/20Thu
2 stops
20h 50mORD-YWG
$370
6/14Fri
nonstopAir Canada
2h 28mYWG-ORD
6/21Fri
1 stopAir Canada
11h 37mORD-YWG
$393
6/13Thu
2 stops
16h 55mYWG-ORD
6/20Thu
3 stops
22h 31mORD-YWG
$395
9/5Thu
nonstopAir Canada
2h 32mYWG-ORD
9/12Thu
1 stopAir Canada
6h 17mORD-YWG
$469
6/13Thu
1 stopPorter Airlines
15h 37mYWG-MDW
6/20Thu
1 stopPorter Airlines
14h 20mMDW-YWG
$469
7/23Tue
nonstopUnited Airlines
2h 28mYWG-ORD
9/10Tue
1 stopUnited Airlines
6h 08mORD-YWG
$483
6/14Fri
nonstopUnited Airlines
2h 28mYWG-ORD
6/21Fri
nonstopUnited Airlines
2h 26mORD-YWG
$487
6/13Thu
1 stopPorter Airlines
10h 17mYWG-MDW
6/20Thu
1 stopPorter Airlines
10h 55mMDW-YWG
$502

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Recent one-way flight deals

6/1Sat
1 stopWestJet
8h 35mYWG-ORD
$145
8/2Fri
1 stopWestJet
8h 27mYWG-ORD
$157
6/1Sat
2 stopsDelta
5h 47mYWG-ORD
$169
8/27Tue
2 stopsDelta
5h 42mYWG-ORD
$180
7/4Thu
1 stop
9h 01mYWG-MDW
$180
9/13Fri
1 stop
12h 49mYWG-MDW
$185
8/27Tue
nonstopUnited Airlines
2h 32mYWG-ORD
$254
9/13Fri
nonstopUnited Airlines
2h 32mYWG-ORD
$260
8/2Fri
nonstopAir Canada
2h 28mYWG-ORD
$576
8/2Fri
nonstopAir Canada
2h 28mYWG-ORD
$720

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Winnipeg - Illinois Flights

Departure:

Winnipeg (YWG)Canada

Return flight deals:

Illinois - Winnipeg

Cabin classes:

$531
$2,001
$227