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$107+ Cheap flights from Winnipeg (YWG) to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORD
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap flight deals from Winnipeg to Illinois

Keep the following information in mind while searching for Winnipeg to Illinois flight deals. Data was last updated septiembre 11, 2025.

Round-trip from

$192
(Trip.com)

One-way from

$107
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$395

Good round-trip deal

$385 or less

Good one-way deal

$329 or less
From Winnipeg to Illinois
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One-way flight from Winnipeg to Illinois
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Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Winnipeg to Illinois.
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Price to beat on a one-way flight from Winnipeg to Illinois.
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Find flight deals from Winnipeg to Illinois

Cheapest flights from Winnipeg to Illinois
Explore the most affordable flight options available from Winnipeg to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/256:30 amYWG - MDW
2 stops16h 17mMultiple Airlines
dom. 10/266:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 9/10$225
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/36:15 pmYWG - ORD
1 stop18h 24mWestJet
dom. 10/55:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 9/9$236
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/258:30 amYWG - ORD
1 stop8h 13mWestJet
dom. 10/262:20 pmORD - YWG
1 stop29h 46mWestJet
Deal found 9/10$237
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/111:20 amYWG - ORD
2 stops32h 24mMultiple Airlines
lun. 10/65:30 pmORD - YWG
1 stop15h 31mMultiple Airlines
Deal found 9/9$253
This oojo deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/186:30 amYWG - ORD
1 stop10h 13mWestJet
jue. 10/235:30 pmORD - YWG
1 stop29h 40mWestJet
Deal found 9/10$262
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/99:00 amYWG - ORD
1 stop14h 39mMultiple Airlines
jue. 10/165:05 amORD - YWG
1 stop11h 17mMultiple Airlines
Deal found 9/11$270
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/267:30 amYWG - MDW
2 stops27h 47mMultiple Airlines
dom. 11/25:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Deal found 9/11$271
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/266:15 amYWG - ORD
1 stop7h 20mMultiple Airlines
dom. 11/26:06 pmORD - YWG
2 stops30h 29mMultiple Airlines
Deal found 9/11$275
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/26:15 pmYWG - ORD
2 stops22h 28mWestJet
dom. 10/55:30 pmORD - YWG
1 stop15h 31mWestJet
Deal found 9/10$276
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/99:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
dom. 10/126:20 amMDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 9/11$278
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/179:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
dom. 10/196:20 amMDW - YWG
2 stops18h 10mMultiple Airlines
Deal found 9/11$288
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/109:00 amYWG - MDW
1 stop14h 46mMultiple Airlines
mar. 10/148:05 amMDW - YWG
2 stops33h 35mMultiple Airlines
Deal found 9/10$315

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 11, 2025.
Use the filters below to find and compare flights from Winnipeg to Illinois that are best for you.

Fly from

Winnipeg

Fly to

Illinois

Route

Depart

Return

Price

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

sáb. 10/25

6:30 am-10:47 pm

2 stops16h 17m

Chicago Midway

dom. 10/26

6:20 am-3:07 pm

1 stop8h 47m

$225

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 10/3

6:15 pm-12:39 pm

1 stop18h 24m

Chicago O'Hare Intl

dom. 10/5

5:30 pm-9:01 am

1 stop15h 31m

$236

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 10/9

9:00 am-11:39 pm

1 stop14h 39m

Chicago O'Hare Intl

jue. 10/16

5:05 am-4:22 pm

1 stop11h 17m

$270

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

dom. 10/26

7:30 am-11:17 am

2 stops27h 47m

Chicago Midway

dom. 11/2

5:20 am-2:07 pm

1 stop8h 47m

$271

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

jue. 10/2

6:15 pm-4:43 pm

2 stops22h 28m

Chicago O'Hare Intl

dom. 10/5

5:30 pm-9:01 am

1 stop15h 31m

$276

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

jue. 10/9

9:00 am-11:46 pm

1 stop14h 46m

Chicago Midway

dom. 10/12

6:20 am-12:30 am

2 stops18h 10m

$278

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 10/4

9:10 am-9:58 pm

1 stop12h 48m

Chicago O'Hare Intl

dom. 10/5

5:30 pm-11:26 am

2 stops17h 56m

$281

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

vie. 10/17

4:30 pm-4:43 pm

2 stops24h 13m

Chicago O'Hare Intl

dom. 10/19

5:30 pm-11:41 am

1 stop18h 11m

$283

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

lun. 9/29

9:00 am-5:26 pm

1 stop8h 26m

Chicago O'Hare Intl

mar. 9/30

5:30 pm-2:30 pm

1 stop21h 00m

$289

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

sáb. 10/25

8:30 am-4:43 pm

1 stop8h 13m

Chicago O'Hare Intl

dom. 10/26

2:20 pm-9:09 pm

2 stops30h 49m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 39 results
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Best time to book a flight from Winnipeg to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Winnipeg to Illinois?

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $245). Flying from Winnipeg to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to IL?

Find hourly flight availability from Winnipeg to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Illinois as you normally would.

Weekly flight availability from Winnipeg to Illinois

Explore weekly flight availability from Winnipeg to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 11, 2025.

The most flights from YWG to USIL are scheduled on a Wednesday (8 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated septiembre 11, 2025.
Get a feel of what it's like to fly with United Airlines and Air Canada from Winnipeg to Illinois by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Comfort

7.3

Entertainment

7.1

Overall

7.4

Food

6.6

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Illinois?

    Winnipeg (YWG), located 4.6 mi from the city center, is the airport you fly out of when you book flights from Winnipeg to Illinois.

  • How long is the flight from Winnipeg to Illinois?

    There are many flights that can get you from Winnipeg to Illinois in 8h 51m. Fly via WestJet or Delta to get the fastest option. Winnipeg and Illinois are separated by a distance of 841 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Winnipeg to Illinois?

    While some choose either Winnipeg - Chicago Midway or Winnipeg - Lambert-St Louis, Winnipeg - Chicago O'Hare Intl is the most popular route from Winnipeg to Illinois.

  • What are the most reliable airlines from Winnipeg to Illinois?

    The top 3 most reliable airlines when flying from Winnipeg to Illinois are Copa Airlines (84%), Avianca (82%) and SkyWest Airlines (77%).

  • What are the cheapest flights from Winnipeg to Illinois?

    Looking for the cheapest flight from Winnipeg to Illinois? While on average our users pay $535, our data indicates the cheapest price to be $189. The most popular route (Winnipeg - Chicago O'Hare Intl), is priced around $206.

  • Can I find deals for flights from Winnipeg to Illinois that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Illinois.

  • Can I find deals for business class flights from Winnipeg to Illinois?

    Yes. Cheapflights offers flight deals from Winnipeg to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Illinois (average of $245). Flying from Winnipeg to Illinois in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Winnipeg to Illinois

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Top 2 airlines flying from Winnipeg to Illinois

Discover the top 2 airlines that operate flights from Winnipeg to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$199Average$546FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$230Average$645FlexibilityNo cancel feeOn-time67%

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