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Cheap flights from Illinois to Winnipeg from C$ 114

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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
26 Dec — 2 Jan1
1 adult
1 adult, Economy, 0 bags

Find 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 26 November 2025.

Tue 2/123:30 p.m.STL - YWG
2 stops23h 37mMultiple Airlines
Sun 14/127:30 a.m.YWG - STL
1 stop26h 22mMultiple Airlines
Deal found 25/11C$ 372
Tue 2/123:30 p.m.STL - YWG
2 stops23h 37mMultiple Airlines
Wed 10/127:30 a.m.YWG - STL
1 stop27h 37mMultiple Airlines
Deal found 25/11C$ 398
Mon 8/129:06 p.m.ORD - YWG
2 stops21h 00mMultiple Airlines
Fri 12/126:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Deal found 24/11C$ 405
Thu 4/123:30 p.m.STL - YWG
2 stops23h 37mMultiple Airlines
Sun 14/127:30 a.m.YWG - STL
1 stop26h 22mMultiple Airlines
Deal found 25/11C$ 411
Wed 3/127:43 p.m.STL - YWG
2 stops43h 24mMultiple Airlines
Wed 10/127:30 a.m.YWG - STL
1 stop27h 37mMultiple Airlines
Deal found 24/11C$ 412
Fri 5/126:11 a.m.ORD - YWG
1 stop8h 56mMultiple Airlines
Tue 9/129:00 p.m.YWG - ORD
2 stops17h 31mMultiple Airlines
Deal found 23/11C$ 439
Mon 8/128:42 p.m.MDW - YWG
2 stops27h 08mMultiple Airlines
Fri 12/127:30 a.m.YWG - MDW
1 stop12h 12mMultiple Airlines
Deal found 24/11C$ 481
Thu 27/1110:12 a.m.ORD - YWG
2 stops28h 55mMultiple Airlines
Sun 7/127:30 a.m.YWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 25/11C$ 587
Fri 28/116:00 a.m.ORD - YWG
1 stop9h 07mMultiple Airlines
Fri 5/126:15 a.m.YWG - ORD
1 stop7h 20mMultiple Airlines
Deal found 24/11C$ 636
Fri 5/126:15 a.m.MDW - YWG
1 stop8h 52mMultiple Airlines
Tue 9/128:05 p.m.YWG - MDW
1 stop14h 00mMultiple Airlines
Deal found 23/11C$ 653
Fri 28/116:05 a.m.MDW - YWG
1 stop9h 02mMultiple Airlines
Fri 5/127:30 a.m.YWG - MDW
1 stop14h 42mMultiple Airlines
Deal found 24/11C$ 698
Tue 23/1210:22 p.m.ORD - YWG
2 stops26h 21mMultiple Airlines
Sun 28/125:40 p.m.YWG - ORD
1 stop8h 12mMultiple Airlines
Deal found 24/11C$ 721

Cheap flight deals from Illinois to Winnipeg

Keep the following information in mind while searching for Illinois to Winnipeg flight deals. Data was last updated 26 November 2025.

Round-trip from

C$ 289

One-way from

C$ 114

Popular in

February

Cheapest in

May

Average price

C$ 782
WestJet
  • WestJet
  • 23/1-26/1
  • 2 total stops
  • 15h 41m total
  • Illinois to Winnipeg
Search Deals
8/1
  • 8/1
  • 1 total stop
  • 22h 18m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 26 November 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

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$ 296

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 23/1

6:20 a.m.-3:07 p.m.

1 stop8h 47m

Winnipeg

Mon 26/1

9:00 p.m.-12:05 p.m.

2 stops15h 05m

C$ 308

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 16/1

6:10 a.m.-3:07 p.m.

1 stop8h 57m

Winnipeg

Mon 19/1

9:00 p.m.-12:05 p.m.

2 stops15h 05m

C$ 308

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 9/1

5:50 a.m.-3:07 p.m.

1 stop9h 17m

Winnipeg

Fri 16/1

7:30 a.m.-10:44 p.m.

1 stop15h 14m

C$ 315

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 1/3

6:00 a.m.-3:09 p.m.

1 stop9h 09m

Winnipeg

Thu 5/3

6:15 a.m.-11:25 p.m.

2 stops17h 10m

C$ 333

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Thu 8/1

3:43 p.m.-3:07 p.m.

1 stop23h 24m

Winnipeg

Thu 15/1

9:00 p.m.-6:51 a.m.

2 stops33h 51m

C$ 343

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 16/1

6:10 a.m.-3:07 p.m.

1 stop8h 57m

Winnipeg

Sun 18/1

8:05 p.m.-10:10 a.m.

1 stop14h 05m

C$ 353

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 8/12

9:06 p.m.-6:06 p.m.

2 stops21h 00m

Winnipeg

Fri 12/12

6:15 a.m.-1:35 p.m.

1 stop7h 20m

C$ 405

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 6/12

7:43 p.m.-3:07 p.m.

2 stops19h 24m

Winnipeg

Wed 10/12

7:30 a.m.-11:07 a.m.

1 stop27h 37m

C$ 436

St. LouisWinnipeg

STL - YWG

STLYWG

Lambert-St Louis

Sat 6/12

7:43 p.m.-3:07 p.m.

2 stops19h 24m

Winnipeg

Sun 14/12

7:30 a.m.-9:52 a.m.

1 stop26h 22m

C$ 436

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/11

Showing 1-10 of 27 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$ 128). Flying from Illinois to Winnipeg in November is currently the most expensive (average of C$ 866). 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 26 November 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 26 November 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.

  • 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 (83%), United Airlines (83%) and Air Canada (82%).

  • 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$ 128). Flying from Illinois to Winnipeg in November is currently the most expensive (average of C$ 866). 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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