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$102+ Cheap flights from Illinois to Winnipeg (YWG)

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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated septiembre 15, 2025.

Round-trip from

$208
(Kiwi.com)

One-way from

$102
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$556

Good round-trip deal

$415 or less
From Illinois to Winnipeg
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One-way flight from Illinois to Winnipeg
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Highest demand for flights based on searches. 0% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 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 Illinois to Winnipeg.
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Find flight deals from Illinois to Winnipeg

Cheapest flights from Illinois to Winnipeg
Explore the most affordable flight options available from Illinois to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
lun. 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
dom. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$208
This Vliegwinkel deal was found by Cheapflights users on 9/15. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/95:30 pmORD - YWG
1 stop29h 40mWestJet
dom. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/15$211
This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 10/105:30 pmORD - YWG
1 stop18h 11mWestJet
dom. 10/128:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/15$215
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 10/115:30 pmORD - YWG
2 stops17h 56mWestJet
vie. 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$216
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 10/125:30 pmORD - YWG
1 stop15h 31mWestJet
vie. 10/178:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/14$218
This oojo deal was found by Cheapflights users on 9/13. 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.
jue. 10/165:30 pmORD - YWG
1 stop18h 11mWestJet
vie. 10/248:30 amYWG - ORD
1 stop8h 13mWestJet
Deal found 9/13$232
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
lun. 10/65:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$233
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 10/83:12 pmORD - YWG
1 stop25h 10mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$234
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
lun. 10/65:30 pmORD - YWG
1 stop15h 31mWestJet
jue. 10/169:05 pmYWG - ORD
1 stop19h 38mWestJet
Deal found 9/14$235
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 10/115:30 pmORD - YWG
2 stops17h 56mMultiple Airlines
lun. 10/139:00 amYWG - ORD
1 stop14h 44mMultiple Airlines
Deal found 9/14$236
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
mar. 10/281:56 pmMDW - YWG
1 stop25h 11mMultiple Airlines
mar. 11/49:00 pmYWG - MDW
2 stops15h 41mMultiple Airlines
Deal found 9/12$256
This Kiwi.com deal was found by Cheapflights users on 9/12. 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. 10/106:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
lun. 10/139:05 pmYWG - MDW
2 stops16h 33mMultiple Airlines
Deal found 9/12$327

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Winnipeg 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 15, 2025.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Illinois

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/9

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

dom. 10/12

8:30 am-4:43 pm

1 stop8h 13m

$208

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/16

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

vie. 10/24

8:30 am-4:43 pm

1 stop8h 13m

$232

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 10/10

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

mié. 10/15

9:05 pm-4:43 pm

1 stop19h 38m

$241

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

vie. 10/10

5:30 pm-5:40 pm

1 stop24h 10m

Winnipeg

lun. 10/13

9:00 am-11:44 pm

1 stop14h 44m

$244

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

mar. 10/28

1:56 pm-3:07 pm

1 stop25h 11m

Winnipeg

mar. 11/4

9:00 pm-12:41 pm

2 stops15h 41m

$256

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 10/6

5:30 pm-9:01 am

1 stop15h 31m

Winnipeg

jue. 10/16

9:00 am-11:39 pm

1 stop14h 39m

$273

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

jue. 10/9

1:26 pm-12:30 am

2 stops11h 04m

Winnipeg

dom. 10/12

8:30 am-4:43 pm

1 stop8h 13m

$275

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

lun. 11/17

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

dom. 11/23

12:55 pm-1:35 pm

3 stops24h 40m

$316

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb. 10/4

1:40 pm-9:25 pm

1 stop7h 45m

Winnipeg

dom. 10/5

6:30 am-8:20 pm

2 stops13h 50m

$325

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

vie. 10/10

6:20 am-4:22 pm

1 stop10h 02m

Winnipeg

lun. 10/13

9:05 pm-1:38 pm

2 stops16h 33m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 40 results
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Best time to book a flight from Illinois to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Illinois 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 Illinois to Winnipeg

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

Currently, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in December is currently the most expensive (average of $501). 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 IL to YWG?

Find hourly flight availability from Illinois to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 15, 2025.

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

Weekly flight availability from Illinois to Winnipeg

Explore weekly flight availability from Illinois to Winnipeg. 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 15, 2025.

The most flights from USIL to YWG are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Winnipeg. 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 into for flights to Winnipeg from Illinois?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Illinois. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • How long is the flight from Illinois to Winnipeg?

    For as low as $208, WestJet can have you in Winnipeg from Illinois in 15h 31m. The distance from Illinois to Winnipeg is about 706 mi.

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

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

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

    Consider SkyWest Airlines (76%), Air Canada (76%) or United Airlines (76%) when booking your flight. These represent the most reliable airlines when flying from Illinois to Winnipeg.

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay $663 for a flight from Illinois to Winnipeg. The cheapest flight overall is $183 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $238.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois to Winnipeg 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 Illinois to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $358). Flying from Illinois to Winnipeg in December is currently the most expensive (average of $501). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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Top 2 airlines flying from Illinois to Winnipeg

Discover the top 2 airlines that operate flights from Illinois to Winnipeg. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$226Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$615FlexibilityNo cancel feeOn-time69%

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