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Cheap flights from Illinois to Winnipeg from C$ 211

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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
11 Aug — 18 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Illinois to Winnipeg

Enter your travel dates to find the best prices.

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 12 July 2026.

Tue 25/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Tue 1/97:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 10/7C$ 471
Fri 28/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 31/89:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 10/7C$ 484
Fri 2/105:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Mon 5/1010:10 a.m.
YWG
-
ORD
2 stops19h 32m
Multiple Airlines
Deal found 11/7C$ 487
Fri 21/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Fri 28/87:00 a.m.
YWG
-
ORD
1 stop9h 40m
WestJet
Deal found 12/7C$ 491
Fri 21/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Fri 28/87:00 a.m.
YWG
-
ORD
2 stops24h 53m
Multiple Airlines
Deal found 12/7C$ 511
Mon 24/87:05 a.m.
ORD
-
YWG
2 stops15h 05m
Multiple Airlines
Mon 31/89:05 p.m.
YWG
-
ORD
1 stop19h 35m
Multiple Airlines
Deal found 10/7C$ 527
Fri 11/95:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 13/99:05 p.m.
YWG
-
ORD
1 stop19h 35m
WestJet
Deal found 10/7C$ 531
Thu 20/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Sun 23/82:55 p.m.
YWG
-
ORD
1 stop25h 45m
WestJet
Deal found 9/7C$ 542
Mon 24/85:30 p.m.
ORD
-
YWG
1 stop7h 25m
WestJet
Mon 31/87:10 p.m.
YWG
-
ORD
1 stop21h 30m
WestJet
Deal found 10/7C$ 545
Thu 20/810:25 a.m.
MDW
-
YWG
1 stop9h 55m
Multiple Airlines
Sun 23/85:10 p.m.
YWG
-
MDW
1 stop16h 35m
Multiple Airlines
Deal found 9/7C$ 565
Thu 27/83:15 p.m.
MDW
-
YWG
1 stop9h 40m
Multiple Airlines
Sun 30/84:15 p.m.
YWG
-
MDW
2 stops17h 30m
Multiple Airlines
Deal found 8/7C$ 614
Thu 1/1012:46 p.m.
STL
-
YWG
1 stop11h 49m
Multiple Airlines
Thu 8/109:05 p.m.
YWG
-
STL
2 stops12h 35m
Multiple Airlines
Deal found 9/7C$ 695

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 12 July 2026.

Round-trip from

C$ 471

One-way from

C$ 211

Popular in

January

Cheapest in

October

Average price

C$ 1,107

Good one-way deal

C$ 583 or less
WestJet
  • WestJet
  • 25/8-1/9
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
WestJet
  • WestJet
  • 4/10
  • 1 total stop
  • 7h 25m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 236 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 105 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 629,999 searches. Data last updated 12 July 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 22/8

4:39 p.m.-3:08 p.m.

2 stops22h 29m

Winnipeg

Sat 29/8

3:58 p.m.-9:59 a.m.

2 stops18h 01m

C$ 746

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Mon 28/9

2:40 p.m.-9:27 p.m.

1 stop6h 47m

Winnipeg

Fri 2/10

10:50 a.m.-6:41 p.m.

1 stop7h 51m

C$ 780

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 21/11

1:39 p.m.-8:48 p.m.

1 stop7h 09m

Winnipeg

Sun 22/11

7:15 a.m.-3:26 p.m.

1 stop8h 11m

C$ 781

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 12/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

Winnipeg

Tue 15/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 783

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 1/10

6:15 a.m.-11:56 a.m.

1 stop5h 41m

Winnipeg

Thu 8/10

6:40 a.m.-11:58 a.m.

1 stop5h 18m

C$ 784

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 26/9

8:03 a.m.-3:19 p.m.

1 stop7h 16m

Winnipeg

Tue 29/9

9:20 a.m.-4:18 p.m.

1 stop6h 58m

C$ 790

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 13/8

12:10 p.m.-9:19 p.m.

1 stop9h 09m

Winnipeg

Wed 19/8

8:15 a.m.-2:02 p.m.

1 stop5h 47m

C$ 815

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 31/7

6:00 a.m.-11:52 a.m.

1 stop5h 52m

Winnipeg

Wed 5/8

12:20 p.m.-8:24 p.m.

1 stop8h 04m

C$ 818

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 31/7

6:30 a.m.-6:10 p.m.

2 stops35h 40m

Winnipeg

Wed 5/8

7:10 p.m.-11:46 a.m.

2 stops16h 36m

C$ 851

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 21/8

9:24 a.m.-7:49 p.m.

2 stops10h 25m

Winnipeg

Fri 28/8

4:15 p.m.-9:40 a.m.

2 stops17h 25m

C$ 852

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/7

Showing 1-10 of 53 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 C$ 88). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,520). 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 12 July 2026.

When flying from Illinois to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 12 July 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?

    Winnipeg (YWG), located 7.3 km from the city centre, is the airport you fly into when you book flights from Illinois to Winnipeg.

  • How long is the flight from Illinois to Winnipeg?

    Airlines like Delta, Air Canada, and Porter Airlines fly from Illinois to Winnipeg in about 6h 47m. The time it takes to get you to your destination can typically vary by up to 15h 42m. There are 1353 km between Illinois and Winnipeg. This flight may include one or multiple stops.

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

    The most popular route from Illinois to Winnipeg is Chicago O'Hare Intl - Winnipeg. You may also consider Chicago Midway - Winnipeg or Lambert-St Louis - Winnipeg.

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

    The top 3 most reliable airlines when flying from Illinois to Winnipeg are Atlas Air (100%), SkyWest Airlines (76%) and Air Canada (76%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 583 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 583 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 565.

  • 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 C$ 88). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,520). 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

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk

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