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$97+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
May 31 — Jun 71
Sun 5/31
Sun 6/7
1 adult, Economy
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Cheap 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 May 1, 2026.

This Trip.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/296:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Deal found 4/26$251
This Trip.com deal was found by Cheapflights users on 4/26. 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.
Sat 5/235:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
Mon 5/257:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/26$255
This Trip.com deal was found by Cheapflights users on 4/26. 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.
Tue 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 6/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/26$256
This Trip.com deal was found by Cheapflights users on 4/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 6/17:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/29$259
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 6/19:05 pm
YWG
-
ORD
2 stops22h 24m
Multiple Airlines
Deal found 4/29$285
This Trip.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/275:30 pm
ORD
-
YWG
1 stop18h 45m
WestJet
Tue 6/27:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 4/27$291
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/265:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Tue 6/29:05 pm
YWG
-
ORD
2 stops34h 50m
Multiple Airlines
Deal found 4/26$299
This FlightHub deal was found by Cheapflights users on 4/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 5/296:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Deal found 4/26$308
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/43:20 pm
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
Mon 6/154:25 pm
YWG
-
MDW
1 stop17h 10m
Multiple Airlines
Deal found 4/30$400
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/193:20 pm
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
Thu 5/216:05 pm
YWG
-
MDW
1 stop20h 30m
Multiple Airlines
Deal found 4/29$402
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Fri 5/2910:30 am
MDW
-
YWG
1 stop9h 19m
Multiple Airlines
Mon 6/18:10 pm
YWG
-
MDW
1 stop13h 25m
Multiple Airlines
Deal found 4/29$413
This FlightHub deal was found by Cheapflights users on 4/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:21 am
STL
-
YWG
1 stop8h 43m
WestJet
Fri 6/195:41 pm
YWG
-
STL
1 stop16h 47m
WestJet
Deal found 4/26$433

Find flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated May 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(Trip.com)

One-way from

$97
(Trip.com)

Popular in

January

Cheapest in

February

Average price

$716

Good round-trip deal

$755 or less

Good one-way deal

$624 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. 22% potential increase in price ($178 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Winnipeg.
Search Deals
Price to beat on a one-way 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 May 1, 2026.
Use the filters below to find and compare flights from Illinois to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 6/14

6:21 am-3:04 pm

1 stop8h 43m

Winnipeg

Fri 6/19

5:41 pm-10:28 am

1 stop16h 47m

$433

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sun 6/7

6:21 am-3:04 pm

1 stop8h 43m

Winnipeg

Sun 6/14

6:15 am-11:56 pm

2 stops17h 41m

$471

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/6

3:20 pm-8:40 am

1 stop17h 20m

Winnipeg

Sun 8/9

6:05 pm-9:40 am

1 stop15h 35m

$474

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 6/12

5:36 pm-4:51 pm

1 stop23h 15m

Winnipeg

Fri 6/19

5:41 pm-11:23 pm

1 stop5h 42m

$487

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Wed 10/14

6:30 am-8:16 pm

1 stop13h 46m

Winnipeg

Sat 10/17

8:00 am-11:18 pm

1 stop15h 18m

$491

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 5/29

8:53 am-12:55 am

2 stops16h 02m

Winnipeg

Fri 6/5

6:00 am-4:46 pm

2 stops10h 46m

$504

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 5/27

9:23 am-4:51 pm

1 stop7h 28m

Winnipeg

Wed 6/3

4:15 pm-2:35 pm

2 stops22h 20m

$595

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 6/13

11:45 am-10:43 am

2 stops22h 58m

Winnipeg

Sat 6/20

9:20 am-4:18 pm

1 stop6h 58m

$646

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 7/22

12:27 pm-11:29 pm

1 stop11h 02m

Winnipeg

Sun 7/26

10:30 pm-4:59 pm

2 stops18h 29m

$667

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 6/26

9:17 am-9:45 am

2 stops24h 28m

Winnipeg

Tue 6/30

4:15 pm-9:40 am

2 stops17h 25m

$688

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 56 resultsSorted by cheapest first
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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, February is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $62). Flying from Illinois to Winnipeg in January is currently the most expensive (average of $1,074). 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 May 1, 2026.

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 27% on airfare.

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 May 1, 2026.

The most flights from USIL to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Illinois to Winnipeg?

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 $251, WestJet can have you in Winnipeg from Illinois in 7h 25m. 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 (57%), Air Canada (57%) or United Airlines (57%) 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 $833 for a flight from Illinois to Winnipeg. The cheapest flight overall is $608 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $285.

  • 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, February is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of $62). Flying from Illinois to Winnipeg in January is currently the most expensive (average of $1,074). 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 3 airlines flying from Illinois to Winnipeg

Discover the top 3 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 May 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$356FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$226Average$509FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$661FlexibilityNo cancel feeOn-time69%

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