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Cheap flights from Illinois to Winnipeg from C$ 152

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 25/1. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — YWG
11 Jan — 18 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 12 December 2025.

Wed 10/124:35 p.m.ORD - YWG
2 stops26h 26mMultiple Airlines
Sun 14/127:30 a.m.YWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 9/12C$ 918
Mon 22/1210:37 a.m.ORD - YWG
1 stop33h 31mMultiple Airlines
Mon 5/18:00 a.m.YWG - ORD
2 stops36h 04mMultiple Airlines
Deal found 11/12C$ 975
Thu 11/125:00 a.m.ORD - YWG
2 stops14h 35mMultiple Airlines
Wed 17/124:55 p.m.YWG - ORD
1 stop27h 28mMultiple Airlines
Deal found 10/12C$ 1,063
Wed 10/122:49 p.m.MDW - YWG
2 stops33h 01mMultiple Airlines
Sun 14/127:30 a.m.YWG - MDW
1 stop10h 42mMultiple Airlines
Deal found 9/12C$ 1,088
Thu 25/129:10 a.m.ORD - YWG
Nonstop2h 47mUnited Airlines
Sun 28/122:20 p.m.YWG - ORD
Nonstop2h 43mUnited Airlines
Deal found 10/12C$ 1,112
Sat 27/128:30 p.m.ORD - YWG
1 stop13h 19mAir Canada
Tue 30/125:30 a.m.YWG - ORD
1 stop14h 15mAir Canada
Deal found 11/12C$ 1,157
Thu 25/123:10 p.m.MDW - YWG
2 stops24h 20mMultiple Airlines
Sun 28/127:30 a.m.YWG - MDW
1 stop14h 42mMultiple Airlines
Deal found 10/12C$ 1,183
Thu 25/128:21 p.m.ORD - YWG
2 stops29h 05mMultiple Airlines
Sun 28/125:40 p.m.YWG - ORD
1 stop8h 12mMultiple Airlines
Deal found 10/12C$ 1,214
Thu 11/121:50 p.m.MDW - YWG
1 stop21h 55mWestJet
Wed 17/125:45 p.m.YWG - MDW
1 stop24h 33mWestJet
Deal found 10/12C$ 1,426
Thu 11/127:44 a.m.MDW - YWG
2 stops16h 58mMultiple Airlines
Wed 17/128:20 p.m.YWG - MDW
1 stop13h 45mMultiple Airlines
Deal found 10/12C$ 1,436
Thu 25/129:50 a.m.MDW - YWG
1 stop29h 17mWestJet
Sun 28/128:05 p.m.YWG - MDW
2 stops15h 01mWestJet
Deal found 11/12C$ 1,596
Wed 10/121:50 p.m.MDW - YWG
1 stop9h 54mWestJet
Sun 14/125:45 p.m.YWG - MDW
1 stop24h 33mWestJet
Deal found 9/12C$ 1,607

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 December 2025.

Round-trip from

C$ 324

One-way from

C$ 152

Popular in

February

Cheapest in

May

Average price

C$ 939
10/1-15/1
  • 10/1-15/1
  • 3 total stops
  • 48h 25m total
  • Illinois to Winnipeg
Search Deals
25/1
  • 25/1
  • 3 total stops
  • 29h 24m total
  • Illinois to Winnipeg
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 38 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 12 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

MDW - YWG

MDWYWG

Chicago Midway

Sun 25/1

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

1 stop8h 47m

Winnipeg

Sun 1/2

7:30 a.m.-10:19 p.m.

1 stop14h 49m

C$ 371

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-11:40 a.m.

1 stop18h 10m

Winnipeg

Sun 7/6

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

1 stop8h 13m

C$ 441

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 30/1

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

1 stop8h 21m

Winnipeg

Mon 2/2

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

1 stop7h 20m

C$ 451

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sun 25/1

8:43 p.m.-12:41 a.m.

3 stops27h 58m

Winnipeg

Sun 1/2

8:20 p.m.-9:03 p.m.

2 stops24h 43m

C$ 488

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 25/5

5:30 p.m.-11:33 a.m.

2 stops18h 03m

Winnipeg

Mon 1/6

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

1 stop8h 13m

C$ 519

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 10/1

6:10 a.m.-12:41 a.m.

2 stops18h 31m

Winnipeg

Thu 15/1

8:20 p.m.-10:10 a.m.

1 stop13h 50m

C$ 521

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 10/1

5:15 a.m.-12:41 a.m.

3 stops19h 26m

Winnipeg

Thu 15/1

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

2 stops21h 02m

C$ 539

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 18/2

1:28 p.m.-11:32 a.m.

2 stops22h 04m

Winnipeg

Sun 22/2

7:30 a.m.-7:59 p.m.

1 stop12h 29m

C$ 542

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 23/4

7:00 a.m.-12:39 a.m.

2 stops17h 39m

Winnipeg

Mon 27/4

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

1 stop8h 13m

C$ 568

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 23/4

7:00 a.m.-12:39 a.m.

2 stops17h 39m

Winnipeg

Thu 30/4

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

1 stop8h 13m

C$ 568

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 36 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 12 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 12 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 and Air Canada fly from Illinois to Winnipeg in about 6h 53m. The time it takes to get you to your destination can typically vary by up to 11h 17m. 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 (73%), United Airlines (73%) and Air Canada (70%).

  • 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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