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$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 8/22. 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
Wed 8/21
Wed 8/28

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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$272

Good to know

Low season

March

High season

July

Cheapest flight

$140
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 2% increase in price.
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 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 $272 one-way - $252 round-trip
  • Morning departure is around 14% 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 1098 reviews
8.2Entertainment
8.6Boarding
8.2Food
8.3Comfort
8.8Crew
Airline reviews

Will try never to fly Delta international again. Flight delayed and staff completely inept in dealing with it. Would not communicate, rude, completely disorganized. Once we reached Seoul the staff there had no idea what to do with us and led us around the airport from one pointless line to another. They were clearly not told how to manage the situation even though they had hours to make a plan. Never again.

2.0 MediocreAnonymous, Jul 2024PDX - SEA
Read more about Korean Air reviews

Will try never to fly Delta international again. Flight delayed and staff completely inept in dealing with it. Would not communicate, rude, completely disorganized. Once we reached Seoul the staff there had no idea what to do with us and led us around the airport from one pointless line to another. They were clearly not told how to manage the situation even though they had hours to make a plan. Never again.

They texted me my gate number and then they texted me again it’s now boarding but in different gate, and the gate was so far from the gate they texted me earlier. I have to run just to get to my flight. They always do that.

The crew and my luggage was still pretty good after a long flight. They take good care of the luggage.

On time departure and exceptional customer service during the entire flight.

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.

I always worry about flying budget airlines but I was impressed by Westjet. The checkin agent was terrific. Seated my husband & me together w/o us asking. TSA checkin was smooth & easy. Plane was clean & comfortable. Drink & snack was unexpected. I will fly with them again.

WiFi was not working. Zero entertainment. Did not receive a discount etc to make up for this.

Calgary WJET supervisor was the most professional, and diligent official who I have experienced personally to resolve our flight issues.

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Flight was canceled last minute and no re-booking was offered. Had to buy a same day flight from another carrier at double the price. I’ll never fly WestJet again.

Flight got cancelled. I had to spend many hours on phone to have it rescheduled at my convenience

Don’t actually know how this flight would have been since we missed it.

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

Constant delays worked out in our favor but definitely extended our travel day

Flight was excellent in all aspects, - comfort , food, drinks, service, entertainment. Inspite of the computer glitch, the flight was on schedule and flawlessly. Thank you, air Canada.

We paid $110 for more leg room. My traveling companion’s knees were right up against the seat in front. Where was more leg room. We feel ripped off. Food,,,there wasn’t any not even a bag of pretzels. As a result, there was very little service.

The crew and the flight was excellent. Captain kept us informed about weather and possibly of turbulence and I appreciated that! The only thing is they didn’t have tv monitors. Other than that, everything was great.

One of the flight attendants was very attentive to a couple traveling with a child under 1 one year old.

We were delayed. Only got 1 snack. Seats were comfortable in preferred seating.

Flight was cancelled. Still stuck at airport. Going on 2 days straight, no sleep. Never fly Air Canada

Terrible. Flight in the morning was circling in air for 45 min due to weather then rerouted to a location further than the final destination to refuel. Sat on tarmac for almost 2 hrs to refuel. Flight was originally to land at 9:30am, we arrived at 2pm and then waited another 30 “for an agent”. Then afternoon return flight was delayed again 3 times for weather then cancelled. Auto rebooked was for the next evening! Just miserable.

It was fine. Give us free headphones or allow Bluetooth or something, or an app to watch on your phone. Grow up

I have never been on an older or dirtier plane.

Book cheap flights from Winnipeg to Illinois

Recent round-trip flight deals

9/6Fri
1 stopWestJet
8h 27mYWG-ORD
9/14Sat
1 stopWestJet
26h 08mORD-YWG
$272
8/20Tue
3 stops
28h 12mYWG-ORD
8/27Tue
3 stops
31h 27mORD-YWG
$297
9/6Fri
1 stopWestJet
25h 37mYWG-ORD
9/14Sat
1 stopWestJet
17h 49mORD-YWG
$299
8/6Tue
2 stops
14h 58mYWG-ORD
8/13Tue
2 stops
18h 13mORD-YWG
$304
8/23Fri
2 stopsAir Canada
13h 47mYWG-ORD
8/25Sun
2 stopsAir Canada
16h 46mORD-YWG
$312
8/23Fri
2 stopsAir Canada
13h 47mYWG-ORD
8/25Sun
2 stopsAir Canada
16h 46mORD-YWG
$321
9/6Fri
2 stopsDelta
25h 18mYWG-ORD
9/14Sat
1 stopDelta
5h 36mORD-YWG
$362
9/6Fri
2 stopsDelta
22h 53mYWG-ORD
9/14Sat
1 stopDelta
5h 36mORD-YWG
$385
8/20Tue
2 stopsPorter Airlines
10h 17mYWG-MDW
8/27Tue
2 stopsPorter Airlines
9h 52mMDW-YWG
$387
8/7Wed
2 stopsPorter Airlines
10h 17mYWG-MDW
8/14Wed
2 stopsPorter Airlines
9h 52mMDW-YWG
$440

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Recent one-way flight deals

8/22Thu
1 stop
9h 05mYWG-MDW
$140
8/22Thu
1 stop
15h 53mYWG-ORD
$145
8/23Fri
1 stop
15h 17mYWG-ORD
$148
8/23Fri
nonstopAir Canada
2h 32mYWG-ORD
$213
8/23Fri
1 stopPorter Airlines
11h 32mYWG-MDW
$213
8/23Fri
nonstopAir Canada
2h 32mYWG-ORD
$219
8/17Sat
1 stopDelta
4h 48mYWG-ORD
$275
8/23Fri
2 stopsWestJet
13h 23mYWG-MDW
$304
12/26Thu
2 stopsWestJet
29h 45mYWG-ORD
$321
8/11Sun
1 stopDelta
4h 48mYWG-ORD
$325

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Last minute flights from Winnipeg to Illinois

Last minute flight, train and bus deals

7/25Thu
multi-stop
12h 58mYWG-ORD
8/25Sun
multi-stop
8h 37mORD-YWG
$371
7/24Wed
multi-stop
8h 47mYWG-ORD
8/25Sun
multi-stop
8h 37mORD-YWG
$383
7/24Wed
multi-stopWestJet
9h 27mYWG-ORD
8/28Wed
multi-stopWestJet
17h 43mORD-YWG
$481
7/25Thu
multi-stopWestJet
10h 07mYWG-ORD
8/28Wed
multi-stopWestJet
17h 43mORD-YWG
$509
7/24Wed
multi-stopAir Canada
7h 54mYWG-ORD
8/25Sun
nonstopAir Canada
2h 26mORD-YWG
$679
7/25Thu
multi-stopAir Canada
6h 25mYWG-ORD
8/31Sat
multi-stopAir Canada
12h 49mORD-YWG
$682
7/25Thu
multi-stopDelta
11h 29mYWG-ORD
8/31Sat
multi-stopDelta
16h 26mORD-YWG
$974
7/23Tue
multi-stopDelta
6h 17mYWG-MDW
7/28Sun
multi-stopDelta
10h 53mMDW-YWG
$1,036
7/24Wed
nonstopUnited Airlines
2h 28mYWG-ORD
8/31Sat
multi-stopUnited Airlines
8h 03mORD-YWG
$1,104
7/23Tue
nonstopUnited Airlines
2h 28mYWG-ORD
7/28Sun
nonstopUnited Airlines
2h 26mORD-YWG
$1,124

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Winnipeg - Illinois Flights

Departure:

Winnipeg (YWG)Canada

Return flight deals:

Illinois - Winnipeg

Cabin classes:

$852
$531
$2,001
$212