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Cheap flights from Illinois to Winnipeg from C$ 164

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 13/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
20 Jan — 27 Jan1
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 21 December 2025.

Sat 27/127:05 p.m.ORD - YWG
1 stop16h 40mWestJet
Tue 30/128:05 p.m.YWG - ORD
2 stops21h 17mWestJet
Deal found 19/12C$ 1,199
Fri 26/126:30 p.m.ORD - YWG
1 stop5h 14mWestJet
Mon 29/1212:20 p.m.YWG - ORD
2 stops20h 41mWestJet
Deal found 20/12C$ 1,389
Fri 26/1211:48 a.m.MDW - YWG
1 stop11h 56mWestJet
Mon 29/1212:20 p.m.YWG - MDW
2 stops20h 29mWestJet
Deal found 20/12C$ 1,396
Fri 26/126:30 p.m.ORD - YWG
1 stop5h 14mMultiple Airlines
Mon 29/1212:10 p.m.YWG - ORD
1 stop7h 14mMultiple Airlines
Deal found 20/12C$ 1,413
Tue 23/126:30 p.m.ORD - YWG
1 stop5h 14mMultiple Airlines
Sat 27/126:00 a.m.YWG - ORD
1 stop6h 33mMultiple Airlines
Deal found 19/12C$ 1,479
Thu 25/126:02 p.m.ORD - YWG
2 stops25h 45mWestJet
Sun 28/125:45 p.m.YWG - ORD
1 stop18h 05mWestJet
Deal found 19/12C$ 1,554
Sat 27/129:10 a.m.ORD - YWG
Nonstop2h 47mAir Canada
Tue 30/125:30 a.m.YWG - ORD
1 stop7h 31mAir Canada
Deal found 19/12C$ 1,581
Thu 25/122:00 p.m.ORD - YWG
1 stop7h 44mAir Canada
Sun 28/122:20 p.m.YWG - ORD
Nonstop2h 43mAir Canada
Deal found 19/12C$ 1,602
Thu 25/125:59 p.m.MDW - YWG
1 stop5h 45mWestJet
Sun 28/125:45 p.m.YWG - MDW
1 stop17h 21mWestJet
Deal found 20/12C$ 1,607
Fri 26/1211:48 a.m.MDW - YWG
1 stop5h 07mMultiple Airlines
Mon 29/124:55 p.m.YWG - MDW
1 stop17h 24mMultiple Airlines
Deal found 20/12C$ 1,613

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 21 December 2025.

Round-trip from

C$ 298

One-way from

C$ 164

Popular in

February

Cheapest in

May

Average price

C$ 969
3/2-10/2
  • 3/2-10/2
  • 3 total stops
  • 59h 24m total
  • Illinois to Winnipeg
Search Deals
13/1
  • 13/1
  • 2 total stops
  • 21h 56m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 21 December 2025.
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

Tue 3/2

2:53 p.m.-3:09 p.m.

1 stop24h 16m

Winnipeg

Tue 10/2

5:55 a.m.-5:03 p.m.

2 stops35h 08m

C$ 298

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-2:30 p.m.

1 stop21h 00m

Winnipeg

Sun 7/6

8:30 a.m.-4:43 p.m.

1 stop8h 13m

C$ 327

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 19/1

11:48 a.m.-12:43 a.m.

1 stop12h 55m

Winnipeg

Mon 26/1

9:00 p.m.-1:58 p.m.

2 stops16h 58m

C$ 327

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 2/2

9:00 a.m.-12:36 a.m.

1 stop15h 36m

Winnipeg

Mon 9/2

8:00 a.m.-7:38 p.m.

1 stop11h 38m

C$ 357

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 8/1

4:49 p.m.-3:07 p.m.

1 stop22h 18m

Winnipeg

Thu 15/1

9:00 p.m.-12:08 p.m.

2 stops15h 08m

C$ 374

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 3/3

5:15 a.m.-12:40 a.m.

3 stops19h 25m

Winnipeg

Wed 4/3

7:30 a.m.-11:47 p.m.

2 stops16h 17m

C$ 457

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 16/1

2:20 p.m.-10:41 p.m.

1 stop8h 21m

Winnipeg

Thu 22/1

9:00 p.m.-1:35 p.m.

1 stop16h 35m

C$ 466

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 2/2

1:00 p.m.-5:26 p.m.

1 stop28h 26m

Winnipeg

Mon 9/2

4:25 p.m.-10:10 a.m.

2 stops17h 45m

C$ 491

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Fri 16/1

5:11 p.m.-1:26 a.m.

1 stop8h 15m

Winnipeg

Fri 23/1

5:05 p.m.-2:46 p.m.

2 stops21h 41m

C$ 506

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 3/3

11:00 a.m.-12:39 a.m.

1 stop13h 39m

Winnipeg

Wed 4/3

7:30 a.m.-7:07 p.m.

1 stop11h 37m

C$ 528

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/12

Showing 1-10 of 32 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 month to book a flight from Illinois to Winnipeg?

Currently, May is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in November is currently the most expensive (average of C$ 847). 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 21 December 2025.

It’s optimal to fly from Illinois to Winnipeg in the morning. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight in the evening.

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 21 December 2025.

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).

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, Air Canada, and Delta fly from Illinois to Winnipeg in about 4h 53m. The time it takes to get you to your destination can typically vary by up to 16h 07m. 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 SkyWest Airlines (59%), United Airlines (59%) and Air Canada (51%).

  • 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, May is the cheapest month in which you can book a flight from Illinois to Winnipeg (average of C$ 123). Flying from Illinois to Winnipeg in November is currently the most expensive (average of C$ 847). 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
Portage la Prairie

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Illinois to Winnipeg?

Cheapflights makes it easy to find Illinois to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Illinois to Winnipeg?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Winnipeg from Illinois.

Can Cheapflights find flights from Illinois to Winnipeg with no change fees?

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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