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Cheap flights from Illinois to Winnipeg from C$ 186

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
16 Sep — 23 Sep1
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 17 August 2026.

Tue 1/95:30 p.m. -
1 stop7h 25m
Sat 5/97:00 a.m. -
1 stop9h 40m
Deal found 13/8C$ 400
Thu 17/95:30 p.m. -
1 stop7h 25m
Sun 20/97:00 a.m. -
1 stop9h 40m
Deal found 12/8C$ 404
Wed 2/92:41 p.m. -
2 stops29h 34m
Fri 11/97:00 a.m. -
1 stop9h 40m
Deal found 12/8C$ 415
Mon 31/85:30 p.m. -
1 stop7h 25m
Sun 6/97:00 a.m. -
1 stop9h 40m
Deal found 12/8C$ 427
Sun 27/95:30 p.m. -
1 stop7h 25m
Sun 4/107:00 a.m. -
1 stop9h 40m
Deal found 13/8C$ 429
Tue 29/95:30 p.m. -
1 stop7h 25m
Tue 6/107:00 a.m. -
1 stop9h 40m
Deal found 15/8C$ 434
Mon 28/95:30 p.m. -
1 stop7h 25m
Mon 5/107:00 a.m. -
1 stop9h 40m
Deal found 14/8C$ 436
Fri 11/95:30 p.m. -
1 stop7h 25m
Fri 18/97:00 a.m. -
1 stop9h 40m
Deal found 12/8C$ 443
Wed 2/95:30 p.m. -
1 stop7h 25m
Sat 5/97:00 a.m. -
1 stop9h 40m
Deal found 14/8C$ 445
Mon 31/85:30 p.m. -
1 stop7h 25m
Thu 10/96:00 a.m. -
2 stops15h 39m
Deal found 12/8C$ 470
Mon 28/92:29 p.m. -
2 stops24h 56m
Mon 5/105:00 p.m. -
1 stop18h 32m
Deal found 13/8C$ 547
Fri 11/99:59 a.m. -
1 stop5h 09m
Fri 18/911:15 a.m. -
2 stops23h 45m
Deal found 12/8C$ 771

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 17 August 2026.

Round-trip from

C$ 400

One-way from

C$ 186

Popular in

August

Cheapest in

February

Average price

C$ 1,742

Good one-way deal

C$ 467 or less
WestJet
  • WestJet
  • 1/9-5/9
  • 2 total stops
  • 17h 05m total
  • Illinois to Winnipeg
Search Deals
2/9
  • 2/9
  • 2 total stops
  • 29h 34m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 25% potential increase in price (C$ 505 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 97 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 17 August 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

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Tue 1/9

5:30 p.m.-12:15 p.m.

1 stop18h 45m

Winnipeg

Sun 6/9

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 663

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Thu 24/9

5:30 p.m.-12:55 a.m.

1 stop7h 25m

Winnipeg

Sun 27/9

7:00 a.m.-4:40 p.m.

1 stop9h 40m

C$ 706

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Sat 26/9

8:45 a.m.-6:12 p.m.

2 stops9h 27m

Winnipeg

Sat 3/10

9:05 p.m.-9:00 a.m.

2 stops11h 55m

C$ 814

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Tue 1/9

12:52 p.m.-3:25 p.m.

2 stops26h 33m

Winnipeg

Wed 2/9

5:42 p.m.-11:26 p.m.

1 stop5h 44m

C$ 828

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Fri 13/11

9:45 a.m.-10:50 p.m.

2 stops13h 05m

Winnipeg

Sat 21/11

5:35 p.m.-11:23 p.m.

1 stop5h 48m

C$ 838

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Mon 16/11

9:45 a.m.-11:54 a.m.

1 stop26h 09m

Winnipeg

Sat 21/11

5:35 p.m.-11:23 p.m.

1 stop5h 48m

C$ 866

ChicagoWinnipeg

ORD Chicago O'Hare Intl - YWG Winnipeg

ORDYWG

Chicago O'Hare Intl

Wed 14/10

11:45 a.m.-7:54 p.m.

1 stop8h 09m

Winnipeg

Wed 21/10

9:20 a.m.-4:19 p.m.

1 stop6h 59m

C$ 873

ChicagoWinnipeg

MDW Chicago Midway - YWG Winnipeg

MDWYWG

Chicago Midway

Fri 25/9

11:45 a.m.-5:58 p.m.

2 stops30h 13m

Winnipeg

Mon 28/9

11:15 a.m.-2:35 p.m.

2 stops27h 20m

C$ 875

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Mon 21/9

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

1 stop5h 52m

Winnipeg

Wed 23/9

7:00 a.m.-3:38 p.m.

1 stop8h 38m

C$ 879

St. LouisWinnipeg

STL Lambert-St Louis - YWG Winnipeg

STLYWG

Lambert-St Louis

Wed 30/9

11:21 a.m.-10:10 p.m.

2 stops10h 49m

Winnipeg

Wed 7/10

8:00 a.m.-4:43 p.m.

1 stop8h 43m

C$ 888

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

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, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 603). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,708). 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 17 August 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 17 August 2026.

The most flights from USIL to YWG are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).

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

Airfare is below average for this route at the moment.
Illinois to Winnipeg flights typically cost between C$ 917 and C$ 1,208 in September.
The cheapest round-trip price found within the last 5 days was C$ 400 on WestJet (1 Sep-5 Sep).

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 WestJet, Porter Airlines, and Delta fly from Illinois to Winnipeg in about 6h 55m. The time it takes to get you to your destination can typically vary by up to 11h 50m. There are 1162 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 Copa Airlines (73%), SkyWest Airlines (63%) and Air Canada (63%).

  • What are the cheapest flights from Illinois to Winnipeg?

    On average you can expect to pay C$ 543 for a flight from Illinois to Winnipeg. The cheapest flight overall is C$ 467 while the most popular route, (Chicago O'Hare Intl - Winnipeg) is currently priced at C$ 505.

  • 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, September is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 603). Flying from Illinois to Winnipeg in January is currently the most expensive (average of C$ 1,708). 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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Yes! Cheapflights helps users easily find flights from Illinois to Winnipeg with no change fees.

Can Cheapflights notify me if prices for flights from Illinois to Winnipeg become cheaper?

Yes! Start tracking prices for Illinois to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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