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$140+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/47:23 pmMDW - YWG
2 stops29h 18mMultiple Airlines
Sun 12/77:30 amYWG - MDW
1 stop26h 22mMultiple Airlines
Deal found 10/29$193
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/92:49 pmMDW - YWG
1 stop24h 18mMultiple Airlines
Fri 12/127:30 amYWG - MDW
1 stop12h 12mMultiple Airlines
Deal found 10/29$203
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
Sun 1/114:55 pmYWG - ORD
1 stop26h 48mMultiple Airlines
Deal found 10/30$218
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Thu 12/45:05 amORD - YWG
2 stops19h 36mMultiple Airlines
Sun 12/77:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 10/30$228
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/910:00 amORD - YWG
2 stops14h 41mMultiple Airlines
Fri 12/127:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 10/29$229
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:05 amORD - YWG
2 stops18h 36mMultiple Airlines
Wed 1/77:30 amYWG - ORD
1 stop16h 31mMultiple Airlines
Deal found 10/29$289
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:05 amORD - YWG
2 stops18h 36mMultiple Airlines
Thu 1/87:30 amYWG - ORD
1 stop13h 31mMultiple Airlines
Deal found 10/29$303
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/95:01 amORD - YWG
1 stop10h 06mMultiple Airlines
Mon 11/1012:55 pmYWG - ORD
2 stops22h 19mMultiple Airlines
Deal found 10/29$316
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/2512:39 pmORD - YWG
1 stop26h 28mMultiple Airlines
Sun 4/268:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 10/29$318
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/3111:45 amORD - YWG
2 stops47h 35mMultiple Airlines
Sun 4/268:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 10/29$327
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/306:00 amORD - YWG
2 stops38h 06mMultiple Airlines
Thu 1/87:30 amYWG - ORD
1 stop13h 31mMultiple Airlines
Deal found 10/29$332
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 11/216:05 amMDW - YWG
1 stop9h 02mMultiple Airlines
Sun 11/237:30 amYWG - MDW
2 stops16h 43mMultiple Airlines
Deal found 10/28$341

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$140
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$574

Good round-trip deal

$1,004 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
Search Deals
From Illinois to Winnipeg
Search Deals
One-way flight from Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Illinois to Winnipeg.
Search Deals

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 October 30, 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

MDW - YWG

MDWYWG

Chicago Midway

Thu 12/4

7:23 pm-3:07 pm

1 stop19h 44m

Winnipeg

Sun 12/7

7:30 am-10:12 pm

1 stop14h 42m

$202

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 12/13

1:24 pm-3:07 pm

1 stop25h 43m

Winnipeg

Sun 1/11

4:55 pm-7:43 pm

1 stop26h 48m

$218

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Mon 3/23

6:15 am-1:35 pm

1 stop7h 20m

$270

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 3/9

2:20 pm-11:52 am

1 stop21h 32m

Winnipeg

Fri 3/13

6:15 am-1:35 pm

1 stop7h 20m

$297

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 1/12

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Thu 1/15

7:50 am-1:35 pm

1 stop29h 45m

$298

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 1/30

6:00 am-3:07 pm

1 stop9h 07m

Winnipeg

Mon 2/2

8:20 pm-10:05 am

1 stop13h 45m

$309

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/13

4:15 pm-11:13 am

2 stops18h 58m

Winnipeg

Mon 3/23

6:00 am-3:20 pm

1 stop9h 20m

$319

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Mon 3/23

9:00 pm-5:12 pm

2 stops20h 12m

$376

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 12/4

4:21 pm-12:41 am

3 stops32h 20m

Winnipeg

Sun 12/7

12:55 pm-6:05 am

2 stops17h 10m

$396

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 12/13

9:59 am-12:42 am

2 stops14h 43m

Winnipeg

Sun 1/11

7:30 am-11:25 pm

1 stop15h 55m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 31 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, May is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $91). Flying from Illinois to Winnipeg in November is currently the most expensive (average of $614). 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 October 30, 2025.

One of the essential ways to save on airfare from Illinois to Winnipeg is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 39% on airfare.

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 $270, WestJet can have you in Winnipeg from Illinois in 8h 20m. The distance from Illinois to Winnipeg is about 706 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Illinois to Winnipeg one-way?

    $273 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and Porter Airlines, with prices starting from $285 and $362, respectively.

  • 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 (89%), Air Canada (89%) or United Airlines (89%) 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 $1,090 for a flight from Illinois to Winnipeg. The cheapest flight overall is $1,004 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $209.

  • 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, May is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $91). Flying from Illinois to Winnipeg in November is currently the most expensive (average of $614). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$230Average$552FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$415Average$614FlexibilityNo cancel feeOn-time69%

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