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$160+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
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 June 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/1810:25 am
MDW
-
YWG
1 stop23h 20m
Multiple Airlines
Sat 7/2511:15 am
YWG
-
MDW
2 stops22h 25m
Multiple Airlines
Deal found 6/18$374
This Mytrip deal was found by Cheapflights users on 6/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/239:50 am
ORD
-
YWG
1 stop15h 05m
Multiple Airlines
Sun 7/266:05 pm
YWG
-
ORD
1 stop14h 55m
Multiple Airlines
Deal found 6/19$375
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 9/65:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sun 9/1311:15 am
YWG
-
ORD
2 stops23h 45m
Multiple Airlines
Deal found 6/20$377
This Trip.com deal was found by Cheapflights users on 6/20. 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.
Sun 9/65:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 9/139:05 pm
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 6/20$389
This Mytrip deal was found by Cheapflights users on 6/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:40 pm
ORD
-
YWG
1 stop14h 32m
Multiple Airlines
Wed 9/3011:40 am
YWG
-
ORD
2 stops9h 55m
Multiple Airlines
Deal found 6/17$400
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/189:57 pm
ORD
-
YWG
2 stops22h 18m
Multiple Airlines
Thu 7/237:00 am
YWG
-
ORD
1 stop9h 40m
Multiple Airlines
Deal found 6/19$420
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Mon 8/105:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sat 8/156:00 am
YWG
-
ORD
1 stop10h 40m
WestJet
Deal found 6/20$458
This Trip.com deal was found by Cheapflights users on 6/18. 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.
Thu 8/275:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 8/302:55 pm
YWG
-
ORD
1 stop25h 45m
WestJet
Deal found 6/18$459
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Mon 8/105:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Sat 8/156:00 am
YWG
-
ORD
2 stops14h 52m
Multiple Airlines
Deal found 6/20$465
This Trip.com deal was found by Cheapflights users on 6/17. 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.
Mon 7/65:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Thu 7/96:15 am
YWG
-
ORD
1 stop8h 07m
Multiple Airlines
Deal found 6/17$468
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Mon 8/103:15 pm
MDW
-
YWG
1 stop18h 30m
Multiple Airlines
Fri 8/148:45 pm
YWG
-
MDW
1 stop12h 55m
Multiple Airlines
Deal found 6/19$474
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
Mon 8/103:15 pm
MDW
-
YWG
2 stops19h 28m
Porter Airlines
Fri 8/148:45 pm
YWG
-
MDW
1 stop12h 55m
Porter Airlines
Deal found 6/19$475

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 June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$374
(Kiwi.com)

One-way from

$160
(Vliegwinkel)

Popular in

January

Cheapest in

February

Average price

$877

Good round-trip deal

$865 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. 14% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($52 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 21, 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

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 7/18

10:25 am-12:55 am

2 stops14h 30m

Winnipeg

Sat 7/25

4:15 pm-9:40 am

2 stops17h 25m

$518

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 9/19

8:03 am-3:19 pm

1 stop7h 16m

Winnipeg

Wed 9/23

11:40 am-8:20 pm

2 stops8h 40m

$550

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 8/10

5:30 pm-12:55 am

1 stop7h 25m

Winnipeg

Sat 8/15

9:05 pm-5:29 pm

3 stops20h 24m

$595

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 7/14

9:19 am-8:40 am

2 stops23h 21m

Winnipeg

Tue 7/21

4:15 pm-9:40 am

2 stops17h 25m

$629

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 7/10

6:00 am-11:52 am

1 stop5h 52m

Winnipeg

Mon 7/13

2:05 pm-8:22 pm

1 stop6h 17m

$649

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 7/7

1:13 pm-10:38 pm

1 stop9h 25m

Winnipeg

Fri 7/10

2:05 pm-8:07 pm

1 stop6h 02m

$649

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 7/6

5:10 am-8:57 pm

1 stop15h 47m

Winnipeg

Fri 7/10

7:00 am-12:11 pm

1 stop5h 11m

$651

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Tue 7/21

9:06 am-8:57 pm

1 stop11h 51m

Winnipeg

Sat 7/25

12:56 pm-6:13 pm

1 stop5h 17m

$651

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 7/18

6:00 am-11:52 am

1 stop5h 52m

Winnipeg

Sat 7/25

7:00 am-2:23 pm

1 stop7h 23m

$651

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 7/18

6:55 pm-11:29 pm

1 stop4h 34m

Winnipeg

Thu 7/23

11:15 am-2:35 pm

2 stops27h 20m

$661

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 43 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 June 21, 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 34% 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 June 21, 2026.

The most flights from USIL to YWG are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 $550, Porter Airlines can have you in Winnipeg from Illinois in 7h 16m. 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 most popular routes from Illinois to Winnipeg?

    While some choose either Lambert-St Louis - Winnipeg or Chicago Midway - 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 (79%), Air Canada (79%) or United Airlines (79%) 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 $1,108 for a flight from Illinois to Winnipeg. The cheapest flight overall is $494 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at $375.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 June 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$208Average$405FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$362Average$714FlexibilityNo cancel feeOn-time69%

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