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Winnipeg

$139+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/272:20 pm
ORD
-
YWG
1 stop8h 20m
WestJet
Fri 3/66:15 am
YWG
-
ORD
1 stop7h 20m
WestJet
Deal found 1/28$241
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 6/67:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$267
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/272:20 pm
ORD
-
YWG
2 stops21h 47m
Multiple Airlines
Fri 3/67:30 am
YWG
-
ORD
1 stop27h 46m
Multiple Airlines
Deal found 1/28$275
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 6/67:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$282
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 6/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$287
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 3/176:00 am
MDW
-
YWG
2 stops18h 40m
Multiple Airlines
Fri 3/207:30 am
YWG
-
MDW
1 stop12h 17m
Multiple Airlines
Deal found 1/28$296
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/15:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 6/107:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$296
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:05 am
ORD
-
YWG
1 stop10h 04m
Multiple Airlines
Mon 3/98:00 am
YWG
-
ORD
1 stop15h 47m
Multiple Airlines
Deal found 1/27$298
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 6/57:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$302
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 3/179:28 am
ORD
-
YWG
2 stops15h 12m
Multiple Airlines
Fri 3/207:30 am
YWG
-
ORD
1 stop15h 09m
Multiple Airlines
Deal found 1/28$303
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Sun 5/35:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Wed 6/107:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 1/28$311
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 2/256:02 pm
ORD
-
YWG
2 stops30h 38m
Multiple Airlines
Wed 3/47:30 am
YWG
-
ORD
1 stop9h 22m
Multiple Airlines
Deal found 1/28$313

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Kiwi.com)

One-way from

$139
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$1,231

Good round-trip deal

$976 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. 30% potential increase in price ($274 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Fri 2/27

2:20 pm-12:07 pm

2 stops21h 47m

Winnipeg

Fri 3/6

7:30 am-11:16 am

1 stop27h 46m

$275

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/17

6:00 am-12:40 am

2 stops18h 40m

Winnipeg

Fri 3/20

7:30 am-7:47 pm

1 stop12h 17m

$296

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 2/26

11:05 am-11:32 am

1 stop24h 27m

Winnipeg

Sun 3/1

8:20 pm-10:05 am

1 stop13h 45m

$367

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 2/27

6:00 am-3:09 pm

1 stop9h 09m

Winnipeg

Fri 3/6

7:30 am-7:47 pm

1 stop12h 17m

$370

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/8

5:15 am-3:09 pm

1 stop9h 54m

Winnipeg

Wed 4/15

7:30 am-10:39 pm

1 stop15h 09m

$392

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 2/25

8:16 pm-12:40 am

3 stops28h 24m

Winnipeg

Wed 3/4

7:30 am-11:47 pm

2 stops16h 17m

$392

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 3/6

6:05 am-3:09 pm

1 stop9h 04m

Winnipeg

Mon 3/9

8:20 pm-8:53 am

2 stops12h 33m

$407

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 3/3

7:00 am-12:40 am

3 stops17h 40m

Winnipeg

Wed 3/4

7:30 am-9:13 pm

2 stops13h 43m

$409

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 3/1

6:51 pm-3:30 pm

2 stops20h 39m

Winnipeg

Wed 3/4

7:30 am-12:40 am

3 stops17h 10m

$429

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 2/26

10:00 am-12:39 am

1 stop14h 39m

Winnipeg

Sun 3/1

5:00 am-1:01 pm

1 stop8h 01m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 35 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 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 January 29, 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 evening could potentially save you up to 22% 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 January 29, 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 $479, WestJet can have you in Winnipeg from Illinois in 8h 19m. The distance from Illinois to Winnipeg is about 841 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 (54%), Air Canada (54%) or United Airlines (54%) 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 $1,160 for a flight from Illinois to Winnipeg. The cheapest flight overall is $973 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $250.

  • 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.

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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Alternative routes for Illinois to Winnipeg

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$156Average$330FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$230Average$515FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$263Average$641FlexibilityNo cancel feeOn-time69%

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