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$135 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 12/15. 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

Search 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

Best Illinois Flight Deals

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

Chicago
Chicago1 stop$261
St. Louis
St. Louis3 stops$545

Good to know

Low season

September

High season

December

Cheapest flight

$135
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 4% 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 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 $335 one-way - $432 round-trip
  • Morning departure is around 112% 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

 
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.
8.5
Korean AirOverall score based on 1043 reviews
8.8Crew
8.3Comfort
8.2Entertainment
8.6Boarding
8.1Food
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 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.

Really good! I like all the crew, they were so nice and very efficient.

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

My flight with Korean Air went quite well, I've flown with them for many years and have grown accustomed to their great service.

The flight crews were extremely professional, helpful, and courteous. Departure and arrival times were accurate. No delay. I will use K airline again. Thanks

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.

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

I had a problem checking in as I didn’t have the correct code. I had to phone BudgetAir.com. They charged me an additional 174US for some tax or something in order to provide me with my booking number. I will never use a third party seller again. Absolutely criminal activity. But I did get to where I wanted to go

Still sitting in a hotel when I'm due for work

My trip was two parts flying from Canada to ATL then to PNS I had confirmed seats with tickets at boarding in Canada and bags tagged for said flight. Got to ATL got help to plane before boarding ended and was told at the gate that I had no seats on this flight even though I had tickets that said so I was told by a supervisor with Delta that I was booked on flight 5 hours later not the one on my ticket had to sit in ATL not knowing if my bags were on flight I was booked on or the one I was told at the gate for 5 hours later or even if I would have seat on that flight as seats were to be assigned at gate. Will never recommend West Jet product and am not sure about Delta any longer and had never booked thru Kayak for flight before and will probably never again and will be sharing my experience with who ever will listen to me about it to warn them to avoid the problems I went thru.

Terrible experience at the gate. Charged for carry on luggage despite them meeting the requirements for sizing.

It was not clear that a shopping bag with gifts would need to be checked. Lucky that my friend checked her carry on so that she could take mine on. It contained fragile items ( and expensive). Plus they charged me $100 for that last minute change.

Never been on a long haul flight that didn't have on flight entertainment. I hope the way back is better !

It was fine for a low cost trip. No entertainment and poor food offer. The sits were ok. It was on time.

Seat barely reclined. Boarding took forever. Flight attendants were not very friendly

Worst airlines. I will never fly this again. Please warn customers. They cancelled our first flight and then gave us flight vouchers that were declined.

Needs to be clearer about baggage allowances upon purchasing tickets

Awful. Late. Basic. Phone charger jacks didn't work. No entertainment No coffee even.

Multiple change of the gates at Pearson, delayed flight was extremely uncomfortable.

The flight went very smoothly, the staff was friendly and very helpful and the pilot flew the plane really, really well. Take off, landing were great and a smooth flight in between!

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

No issues with the flight and flight crew. cleaner seats in economy section would have been better

Very good. But seat selection was not good. We were put on different rows. Would have been nicer to sit besides each other as a couple.

Air Canada is great! Got to my destination earlier than expected and was a smooth ride the whole way there.

I have flown on many airlines all over the world, and this plane flight was the most uncomfortable I have ever experienced.

Boarding was OK. The overhead bins on the Havilland 400 are smaller than the allowable carry on bag sizes, making the bags to be jammed in and as a result slowing the boarding process.

After i biked my flights, i was informed my flight was rescheduled for later time

Book cheap flights from Winnipeg to Illinois

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Winnipeg to Illinois found on KAYAK in the last 72 hours.
11/12Tue
1 stop
9h 26mYWG-ORD
11/26Tue
1 stop
9h 55mORD-YWG
$261
11/5Tue
2 stops
21h 58mYWG-ORD
11/7Thu
1 stop
11h 27mORD-YWG
$343
2/13Thu
1 stopWestJet
7h 41mYWG-ORD
2/17Mon
1 stopWestJet
7h 59mORD-YWG
$382
12/3Tue
1 stopAir Canada
7h 00mYWG-ORD
12/16Mon
nonstopAir Canada
2h 36mORD-YWG
$395
1/29Wed
1 stopAir Canada
7h 00mYWG-ORD
2/5Wed
1 stopAir Canada
9h 08mORD-YWG
$403
11/28Thu
nonstopUnited Airlines
2h 30mYWG-ORD
12/2Mon
nonstopUnited Airlines
2h 36mORD-YWG
$405
12/5Thu
1 stopUnited Airlines
17h 01mYWG-ORD
12/12Thu
1 stopUnited Airlines
15h 51mORD-YWG
$409
11/16Sat
1 stopDelta
6h 01mYWG-MDW
11/29Fri
1 stopDelta
4h 10mMDW-YWG
$432
11/16Sat
2 stopsDelta
8h 36mYWG-ORD
11/28Thu
1 stopDelta
5h 13mORD-YWG
$432
1/29Wed
1 stopWestJet
24h 40mYWG-MDW
2/5Wed
1 stopWestJet
7h 40mMDW-YWG
$442

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Winnipeg to Illinois found on KAYAK in the last 72 hours.
12/15Sun
1 stop
16h 21mYWG-ORD
$135
11/3Sun
1 stop
24h 50mYWG-MDW
$152
1/9Thu
1 stopAir Canada
7h 00mYWG-ORD
$225
1/10Fri
nonstopAir Canada
2h 36mYWG-ORD
$226
12/5Thu
1 stopUnited Airlines
17h 01mYWG-ORD
$232
1/9Thu
2 stopsDelta
8h 53mYWG-ORD
$264
10/30Wed
2 stopsWestJet
16h 38mYWG-MDW
$283
10/30Wed
2 stopsWestJet
31h 08mYWG-ORD
$317
1/9Thu
nonstopUnited Airlines
2h 36mYWG-ORD
$371
12/5Thu
1 stopDelta
6h 01mYWG-MDW
$479

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Last minute flights from Winnipeg to Illinois

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Winnipeg to Illinois that are departing in the next 10 days.
10/26Sat
multi-stop
14h 25mYWG-ORD
10/28Mon
multi-stop
16h 25mORD-YWG
$323
10/26Sat
multi-stop
22h 18mYWG-ORD
10/28Mon
multi-stop
20h 06mORD-YWG
$450
10/26Sat
multi-stopAir Canada
7h 23mYWG-ORD
10/28Mon
multi-stopAir Canada
11h 14mORD-YWG
$891
10/25Fri
multi-stopAir Canada
7h 53mYWG-ORD
10/28Mon
multi-stopAir Canada
12h 03mORD-YWG
$896
10/22Tue
multi-stopPorter Airlines
10h 17mYWG-MDW
10/29Tue
multi-stopPorter Airlines
9h 54mMDW-YWG
$912
10/26Sat
multi-stopPorter Airlines
28h 20mYWG-MDW
10/28Mon
multi-stopPorter Airlines
27h 34mMDW-YWG
$929
10/26Sat
multi-stopWestJet
5h 49mYWG-MDW
10/28Mon
multi-stopWestJet
25h 56mMDW-YWG
$1,002
10/25Fri
multi-stopDelta
11h 33mYWG-ORD
10/27Sun
multi-stopDelta
6h 02mORD-YWG
$1,002
10/25Fri
multi-stopWestJet
26h 03mYWG-MDW
10/28Mon
multi-stopWestJet
13h 52mMDW-YWG
$1,043
10/22Tue
multi-stopDelta
9h 12mYWG-MDW
10/24Thu
multi-stopDelta
10h 33mMDW-YWG
$1,116

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

Information on your arrival and departure airports